66508-37-0,MFCD27986862
Catalog No.:AA00FCUT

66508-37-0 | FOSMIDOMYCIN, SODIUM SALT

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1mg
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5mg
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$246.00   $172.00
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10mg
≥95%
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25mg
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
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Technical Information
Catalog Number:
AA00FCUT
Chemical Name:
FOSMIDOMYCIN, SODIUM SALT
CAS Number:
66508-37-0
Molecular Formula:
C4H9NNaO5P
Molecular Weight:
205.0815
MDL Number:
MFCD27986862
SMILES:
O=CN(CCCP(=O)(O[Na])O)O
Properties
Properties
 
Form:
Solid  
MP:
78-81°C  
Storage:
-20 ℃;Keep in dry area;  

Computed Properties
 
Complexity:
177  
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  

Literature

Title: IspC as target for antiinfective drug discovery: synthesis, enantiomeric separation, and structural biology of fosmidomycin thia isosters.

Journal: Journal of medicinal chemistry 20131024

Title: Improved efficacy of fosmidomycin against Plasmodium and Mycobacterium species by combination with the cell-penetrating peptide octaarginine.

Journal: Antimicrobial agents and chemotherapy 20131001

Title: DXR inhibition by potent mono- and disubstituted fosmidomycin analogues.

Journal: Journal of medicinal chemistry 20130808

Title: Isoprenoid biosynthesis inhibition disrupts Rab5 localization and food vacuolar integrity in Plasmodium falciparum.

Journal: Eukaryotic cell 20130201

Title: Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR).

Journal: Bioorganic & medicinal chemistry letters 20121101

Title: α-Substituted β-oxa isosteres of fosmidomycin: synthesis and biological evaluation.

Journal: Journal of medicinal chemistry 20120726

Title: The isoprenoid-precursor dependence of Plasmodium spp.

Journal: Natural product reports 20120701

Title: Crystal structure of Brucella abortus deoxyxylulose-5-phosphate reductoisomerase-like (DRL) enzyme involved in isoprenoid biosynthesis.

Journal: The Journal of biological chemistry 20120504

Title: Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.

Journal: European journal of medicinal chemistry 20120501

Title: Changes in the hydrocarbon-synthesizing activity during growth of Botryococcus braunii B70.

Journal: Bioresource technology 20120401

Title: Remodeling the isoprenoid pathway in tobacco by expressing the cytoplasmic mevalonate pathway in chloroplasts.

Journal: Metabolic engineering 20120101

Title: Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr): a review of the synthesis and biological evaluation of recent inhibitors.

Journal: Current topics in medicinal chemistry 20120101

Title: Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs.

Journal: Bioorganic & medicinal chemistry letters 20111201

Title: Floral odor bouquet loses its ant repellent properties after inhibition of terpene biosynthesis.

Journal: Journal of chemical ecology 20111201

Title: Synthesis of functionalized cinnamaldehyde derivatives by an oxidative Heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors.

Journal: The Journal of organic chemistry 20111104

Title: New N-acetyltransferase fold in the structure and mechanism of the phosphonate biosynthetic enzyme FrbF.

Journal: The Journal of biological chemistry 20111014

Title: Reverse fosmidomycin derivatives against the antimalarial drug target IspC (Dxr).

Journal: Journal of medicinal chemistry 20111013

Title: Characterization and application of the Fe(II) and α-ketoglutarate dependent hydroxylase FrbJ.

Journal: Chemical communications (Cambridge, England) 20110928

Title: Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: an attempt to improve the activity against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20110915

Title: Resistance of the Burkholderia cepacia complex to fosmidomycin and fosmidomycin derivatives.

Journal: International journal of antimicrobial agents 20110901

Title: Chemical rescue of malaria parasites lacking an apicoplast defines organelle function in blood-stage Plasmodium falciparum.

Journal: PLoS biology 20110801

Title: Design, synthesis, and X-ray crystallographic studies of α-aryl substituted fosmidomycin analogues as inhibitors of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Journal: Journal of medicinal chemistry 20110728

Title: Isoprene synthesis in plants: lessons from a transgenic tobacco model.

Journal: Plant, cell & environment 20110601

Title: Induction of a longer term component of isoprene release in darkened aspen leaves: origin and regulation under different environmental conditions.

Journal: Plant physiology 20110601

Title: A second target of the antimalarial and antibacterial agent fosmidomycin revealed by cellular metabolic profiling.

Journal: Biochemistry 20110503

Title: A high-throughput screening assay for simultaneous selection of inhibitors of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate synthase (Dxs) or 1-deoxy-D-xylulose 5-phosphate reductoisomerase (Dxr).

Journal: Journal of biomolecular screening 20110301

Title: Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors.

Journal: Bioorganic & medicinal chemistry 20110201

Title: Fosmidomycin uptake into Plasmodium and Babesia-infected erythrocytes is facilitated by parasite-induced new permeability pathways.

Journal: PloS one 20110101

Title: Isoprenoid precursor biosynthesis offers potential targets for drug discovery against diseases caused by apicomplexan parasites.

Journal: Current topics in medicinal chemistry 20110101

Title: Evidence of isoprenoid precursor toxicity in Bacillus subtilis.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Characterization and structure of DhpI, a phosphonate O-methyltransferase involved in dehydrophos biosynthesis.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20101012

Title: Synthesis and antiplasmodial activity of highly active reverse analogues of the antimalarial drug candidate fosmidomycin.

Journal: ChemMedChem 20101004

Title: Crystal structure of 1-deoxy-d-xylulose 5-phosphate reductoisomerase from the hyperthermophile Thermotoga maritima for insights into the coordination of conformational changes and an inhibitor binding.

Journal: Journal of structural biology 20100601

Title: Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase.

Journal: The Journal of organic chemistry 20100521

Title: Effects of fosmidomycin on plant photosynthesis as measured by gas exchange and chlorophyll fluorescence.

Journal: Photosynthesis research 20100401

Title: A high-throughput colorimetric-based bioassay method for determination of fosmidomycin in plasma and urine and application for pharmacokinetic study.

Journal: Journal of pharmacological and toxicological methods 20100101

Title: The malarial drug target Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (PfDXR): development of a 3-D model for identification of novel, structural and functional features and for inhibitor screening.

Journal: Protein and peptide letters 20100101

Title: Coordination chemistry based approach to lipophilic inhibitors of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.

Journal: Journal of medicinal chemistry 20091112

Title: Chemical genomics in Escherichia coli identifies an inhibitor of bacterial lipoprotein targeting.

Journal: Nature chemical biology 20091101

Title: The carotenogenesis pathway via the isoprenoid-beta-carotene interference approach in a new strain of Dunaliella salina isolated from Baja California Mexico.

Journal: Marine drugs 20090301

Title: The plastidial 2-C-methyl-D-erythritol 4-phosphate pathway provides the isoprenyl moiety for protein geranylgeranylation in tobacco BY-2 cells.

Journal: The Plant cell 20090101

Title: Use of high-density tiling microarrays to identify mutations globally and elucidate mechanisms of drug resistance in Plasmodium falciparum.

Journal: Genome biology 20090101

Title: The biosynthesis and accumulation of beta-carotene in Dunaliella salina proceed via the glyceraldehyde 3-phosphate/pyruvate pathway.

Journal: Natural product research 20090101

Title: Kinetic characterization and phosphoregulation of the Francisella tularensis 1-deoxy-D-xylulose 5-phosphate reductoisomerase (MEP synthase).

Journal: PloS one 20090101

Title: Isoprene and nitric oxide reduce damages in leaves exposed to oxidative stress.

Journal: Plant, cell & environment 20081201

Title: Studies addressing the importance of charge in the binding of fosmidomycin-like molecules to deoxyxylulosephosphate reductoisomerase.

Journal: ChemMedChem 20080801

Title: Significance of terpenoids in induced indirect plant defence against herbivorous arthropods.

Journal: Plant, cell & environment 20080401

Title: Towards new antimalarial drugs: synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors.

Journal: Chemistry & biodiversity 20080401

Title: Synthesis of beta- and gamma-oxa isosteres of fosmidomycin and FR900098 as antimalarial candidates.

Journal: Bioorganic & medicinal chemistry 20080315

Title: Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake.

Journal: BMC microbiology 20080101

Title: Assessment of the pharmacokinetics and dynamics of two combination regimens of fosmidomycin-clindamycin in patients with acute uncomplicated falciparum malaria.

Journal: Malaria journal 20080101

Title: gamma-Substituted bis(pivaloyloxymethyl)ester analogues of fosmidomycin and FR900098.

Journal: Archiv der Pharmazie 20071201

Title: Synthesis and evaluation of alpha,beta-unsaturated alpha-aryl-substituted fosmidomycin analogues as DXR inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20070901

Title: Assessment of in vitro antimalarial interactions between dihydroartemisinin and fosmidomycin.

Journal: The Southeast Asian journal of tropical medicine and public health 20070901

Title: The methylerythritol phosphate pathway for isoprenoid biosynthesis in coccidia: presence and sensitivity to fosmidomycin.

Journal: Experimental parasitology 20070801

Title: An Escherichia coli undecaprenyl-pyrophosphate phosphatase implicated in undecaprenyl phosphate recycling.

Journal: Microbiology (Reading, England) 20070801

Title: Molecular epidemiology of malaria in Cameroon. XXV. In vitro activity of fosmidomycin and its derivatives against fresh clinical isolates of Plasmodium falciparum and sequence analysis of 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Journal: The American journal of tropical medicine and hygiene 20070801

Title: Structures of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase provide new insights into catalysis.

Journal: The Journal of biological chemistry 20070706

Title: Conformationally restrained aromatic analogues of fosmidomycin and FR900098.

Journal: Archiv der Pharmazie 20070701

Title: Structure of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in a quaternary complex with a magnesium ion, NADPH and the antimalarial drug fosmidomycin.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20070601

Title: Effect of fosmidomycin on metabolic and transcript profiles of the methylerythritol phosphate pathway in Plasmodium falciparum.

Journal: Memorias do Instituto Oswaldo Cruz 20070601

Title: Divergent strategy for the synthesis of alpha-aryl-substituted fosmidomycin analogues.

Journal: The Journal of organic chemistry 20070511

Title: Bioassay for determination of fosmidomycin in plasma and urine: application for pharmacokinetic dose optimisation.

Journal: Journal of microbiological methods 20070401

Title: Pharmacokinetics and pharmacodynamics of fosmidomycin monotherapy and combination therapy with clindamycin in the treatment of multidrug resistant falciparum malaria.

Journal: Malaria journal 20070101

Title: [Evaluation of in vitro antibacterial activity of fosmidomycin and its derivatives].

Journal: Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 20070101

Title: Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.

Journal: Journal of medicinal chemistry 20061214

Title: Arylmethyl substituted derivatives of Fosmidomycin: synthesis and antimalarial activity.

Journal: European journal of medicinal chemistry 20061201

Title: Isoprenoid biosynthesis in plants - 2C-methyl-D-erythritol-4-phosphate synthase (IspC protein) of Arabidopsis thaliana.

Journal: The FEBS journal 20061001

Title: Synthesis and antimalarial activity of chain substituted pivaloyloxymethyl ester analogues of Fosmidomycin and FR900098.

Journal: Bioorganic & medicinal chemistry 20060801

Title: The relationship between the methyl-erythritol phosphate pathway leading to emission of volatile isoprenoids and abscisic acid content in leaves.

Journal: Plant physiology 20060801

Title: Plastid cues posttranscriptionally regulate the accumulation of key enzymes of the methylerythritol phosphate pathway in Arabidopsis.

Journal: Plant physiology 20060501

Title: Involvement of 2-C-methyl-D-erythritol-4-phosphate pathway in biosynthesis of aphidicolin-like tetracyclic diterpene of Scoparia dulcis.

Journal: Chemical & pharmaceutical bulletin 20060501

Title: Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors.

Journal: Journal of medicinal chemistry 20060420

Title: Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Journal: Bioorganic & medicinal chemistry 20060401

Title: Synthesis of alpha-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20060401

Title: A fragment-based approach to understanding inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.

Journal: Chembiochem : a European journal of chemical biology 20051001

Title: Fosmidomycin analogues as inhibitors of monoterpenoid indole alkaloid production in Catharanthus roseus cells.

Journal: Phytochemistry 20050801

Title: Alkoxycarbonyloxyethyl ester prodrugs of FR900098 with improved in vivo antimalarial activity.

Journal: Archiv der Pharmazie 20050701

Title: AFMoC enhances predictivity of 3D QSAR: a case study with DOXP-reductoisomerase.

Journal: Journal of medicinal chemistry 20050519

Title: Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations.

Journal: Journal of medicinal chemistry 20050505

Title: Isoprene decreases the concentration of nitric oxide in leaves exposed to elevated ozone.

Journal: The New phytologist 20050501

Title: [Effects of fosmidomycin and lovastatin treatment on taxol biosynthesis in suspension culture cells of Taxus chinensis].

Journal: Zhi wu sheng li yu fen zi sheng wu xue xue bao = Journal of plant physiology and molecular biology 20050401

Title: Isoprenoid biosynthesis as a target for antibacterial and antiparasitic drugs: phosphonohydroxamic acids as inhibitors of deoxyxylulose phosphate reducto-isomerase.

Journal: The Biochemical journal 20050215

Title: The crystal structure of E.coli 1-deoxy-D-xylulose-5-phosphate reductoisomerase in a ternary complex with the antimalarial compound fosmidomycin and NADPH reveals a tight-binding closed enzyme conformation.

Journal: Journal of molecular biology 20050107

Title: [Prevalence of nonmevalonate and mevalonate pathways for isoprenoid biosynthesis among bacteria of different systematic groups].

Journal: Mikrobiologiia 20050101

Title: [Isoprenoid pigments in representatives of the family Microbacteriaceae].

Journal: Mikrobiologiia 20050101

Title: The plastid of Plasmodium spp.: a target for inhibitors.

Journal: Current topics in microbiology and immunology 20050101

Title: The methylerythritol phosphate pathway is functionally active in all intraerythrocytic stages of Plasmodium falciparum.

Journal: The Journal of biological chemistry 20041210

Title: 1-Deoxy-D-xylulose 5-phosphate reductoisomerase: an overview.

Journal: Bioorganic chemistry 20041201

Title: Synthesis and biological evaluation with plant cells of new fosmidomycin analogues containing a benzoxazolone or oxazolopyridinone ring.

Journal: Journal of enzyme inhibition and medicinal chemistry 20041201

Title: Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: synthesis and evaluation.

Journal: Bioorganic & medicinal chemistry letters 20041101

Title: Fosmidomycin-clindamycin for the treatment of Plasmodium falciparum malaria.

Journal: The Journal of infectious diseases 20041101

Title: Crystallographic structures of two bisphosphonate:1-deoxyxylulose-5-phosphate reductoisomerase complexes.

Journal: Journal of the American Chemical Society 20040908

Title: Determination of fosmidomycin in human serum and urine by capillary electrophoresis.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040705

Title: Impact of ozone on monoterpene emissions and evidence for an isoprene-like antioxidant action of monoterpenes emitted by Quercus ilex leaves.

Journal: Tree physiology 20040401

Title: Fosmidomycin-clindamycin for Plasmodium falciparum Infections in African children.

Journal: The Journal of infectious diseases 20040301

Title: Distinct light-mediated pathways regulate the biosynthesis and exchange of isoprenoid precursors during Arabidopsis seedling development.

Journal: The Plant cell 20040101

Title: The MEP pathway: a new target for the development of herbicides, antibiotics and antimalarial drugs.

Journal: Current pharmaceutical design 20040101

Title: Molecular cloning and functional expression of geranylgeranyl pyrophosphate synthase from Coleus forskohlii Briq.

Journal: BMC plant biology 20040101

Title: Methyl palmitate: a novel product of the Medfly (Ceratitis capitata) corpus allatum.

Journal: Insect biochemistry and molecular biology 20031201

Title: New antimalarial drugs.

Journal: Angewandte Chemie (International ed. in English) 20031110

Title: Fosmidomycin resistance in adenylate cyclase deficient (cya) mutants of Escherichia coli.

Journal: Bioscience, biotechnology, and biochemistry 20030901

Title: Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells.

Journal: The Journal of biological chemistry 20030718

Title: Acyloxyalkyl ester prodrugs of FR900098 with improved in vivo anti-malarial activity.

Journal: Bioorganic & medicinal chemistry letters 20030707

Title: High-throughput screen for inhibitors of 1-deoxy-d-xylulose 5-phosphate reductoisomerase by surrogate ligand competition.

Journal: Journal of biomolecular screening 20030601

Title: Fosmidomycin for the treatment of malaria.

Journal: Parasitology research 20030601

Title: Structural basis of fosmidomycin action revealed by the complex with 2-C-methyl-D-erythritol 4-phosphate synthase (IspC). Implications for the catalytic mechanism and anti-malaria drug development.

Journal: The Journal of biological chemistry 20030516

Title: Natural abundance carbon isotope composition of isoprene reflects incomplete coupling between isoprene synthesis and photosynthetic carbon flow.

Journal: Plant physiology 20030401

Title: Inhibition of paclitaxel and baccatin III accumulation by mevinolin and fosmidomycin in suspension cultures of Taxus baccata.

Journal: Journal of biotechnology 20030306

Title: Fosmidomycin, a novel chemotherapeutic agent for malaria.

Journal: Antimicrobial agents and chemotherapy 20030201

Title: Role of the non-mevalonate pathway in indole alkaloid production by Catharanthus roseus hairy roots.

Journal: Biotechnology progress 20030101

Title: [Effect of fosfidomycin on development of various infections in mice].

Journal: Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 20030101

Title: Alternative pathways of carotenoid biosynthesis in prokaryotes and eukaryotes.

Journal: Doklady. Biochemistry and biophysics 20030101

Title: Fosmidomycin for malaria.

Journal: Lancet (London, England) 20021214

Title: Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics.

Journal: Plant physiology 20021101

Title: On-line analysis of the (13)CO(2) labeling of leaf isoprene suggests multiple subcellular origins of isoprene precursors.

Journal: Planta 20021001

Title: Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units.

Journal: Bioscience, biotechnology, and biochemistry 20020801

Title: Antisense and chemical suppression of the nonmevalonate pathway affects ent-kaurene biosynthesis in Arabidopsis.

Journal: Planta 20020601

Title: E. coli MEP synthase: steady-state kinetic analysis and substrate binding.

Journal: Biochemistry 20020108

Title: Isoprene produced by leaves protects the photosynthetic apparatus against ozone damage, quenches ozone products, and reduces lipid peroxidation of cellular membranes.

Journal: Plant physiology 20011201

Title: Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.

Journal: Plant physiology 20011001

Title: 1-Deoxy-D-xylulose 5-phosphate reductoisomerase and plastid isoprenoid biosynthesis during tomato fruit ripening.

Journal: The Plant journal : for cell and molecular biology 20010801

Title: Isoprene increases thermotolerance of fosmidomycin-fed leaves.

Journal: Plant physiology 20010401

Title: Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs.

Journal: Science (New York, N.Y.) 19990903

Title: Kojo H, et al. FR-31564, a new phosphonic acid antibiotic: bacterial resistance and membrane permeability. J Antibiot (Tokyo). 1980 Jan;33(1):44-8.

Title: Fernandes JF, et al. Fosmidomycin as an antimalarial drug: a meta-analysis of clinical trials. Future Microbiol. 2015;10(8):1375-90.

Title: Jomaa H, et al. Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science. 1999 Sep 3;285(5433):1573-6.

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Tags:66508-37-0 Molecular Formula|66508-37-0 MDL|66508-37-0 SMILES|66508-37-0 FOSMIDOMYCIN, SODIUM SALT
Catalog No.: AA00FCUT
66508-37-0,MFCD27986862
66508-37-0 | FOSMIDOMYCIN, SODIUM SALT
Pack Size: 1mg
Purity: ≥95%
in stock
$63.00 $44.00
Pack Size: 5mg
Purity: ≥95%
in stock
$246.00 $172.00
Pack Size: 10mg
Purity: ≥95%
in stock
$459.00 $321.00
Pack Size: 25mg
Purity: ≥95%
in stock
$972.00 $680.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA00FCUT
Chemical Name: FOSMIDOMYCIN, SODIUM SALT
CAS Number: 66508-37-0
Molecular Formula: C4H9NNaO5P
Molecular Weight: 205.0815
MDL Number: MFCD27986862
SMILES: O=CN(CCCP(=O)(O[Na])O)O
Properties
Form: Solid  
MP: 78-81°C  
Storage: -20 ℃;Keep in dry area;  
Complexity: 177  
Covalently-Bonded Unit Count: 2  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 12  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 4  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
Literature fold

Title: IspC as target for antiinfective drug discovery: synthesis, enantiomeric separation, and structural biology of fosmidomycin thia isosters.

Journal: Journal of medicinal chemistry20131024

Title: Improved efficacy of fosmidomycin against Plasmodium and Mycobacterium species by combination with the cell-penetrating peptide octaarginine.

Journal: Antimicrobial agents and chemotherapy20131001

Title: DXR inhibition by potent mono- and disubstituted fosmidomycin analogues.

Journal: Journal of medicinal chemistry20130808

Title: Isoprenoid biosynthesis inhibition disrupts Rab5 localization and food vacuolar integrity in Plasmodium falciparum.

Journal: Eukaryotic cell20130201

Title: Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR).

Journal: Bioorganic & medicinal chemistry letters20121101

Title: α-Substituted β-oxa isosteres of fosmidomycin: synthesis and biological evaluation.

Journal: Journal of medicinal chemistry20120726

Title: The isoprenoid-precursor dependence of Plasmodium spp.

Journal: Natural product reports20120701

Title: Crystal structure of Brucella abortus deoxyxylulose-5-phosphate reductoisomerase-like (DRL) enzyme involved in isoprenoid biosynthesis.

Journal: The Journal of biological chemistry20120504

Title: Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.

Journal: European journal of medicinal chemistry20120501

Title: Changes in the hydrocarbon-synthesizing activity during growth of Botryococcus braunii B70.

Journal: Bioresource technology20120401

Title: Remodeling the isoprenoid pathway in tobacco by expressing the cytoplasmic mevalonate pathway in chloroplasts.

Journal: Metabolic engineering20120101

Title: Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr): a review of the synthesis and biological evaluation of recent inhibitors.

Journal: Current topics in medicinal chemistry20120101

Title: Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs.

Journal: Bioorganic & medicinal chemistry letters20111201

Title: Floral odor bouquet loses its ant repellent properties after inhibition of terpene biosynthesis.

Journal: Journal of chemical ecology20111201

Title: Synthesis of functionalized cinnamaldehyde derivatives by an oxidative Heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors.

Journal: The Journal of organic chemistry20111104

Title: New N-acetyltransferase fold in the structure and mechanism of the phosphonate biosynthetic enzyme FrbF.

Journal: The Journal of biological chemistry20111014

Title: Reverse fosmidomycin derivatives against the antimalarial drug target IspC (Dxr).

Journal: Journal of medicinal chemistry20111013

Title: Characterization and application of the Fe(II) and α-ketoglutarate dependent hydroxylase FrbJ.

Journal: Chemical communications (Cambridge, England)20110928

Title: Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: an attempt to improve the activity against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters20110915

Title: Resistance of the Burkholderia cepacia complex to fosmidomycin and fosmidomycin derivatives.

Journal: International journal of antimicrobial agents20110901

Title: Chemical rescue of malaria parasites lacking an apicoplast defines organelle function in blood-stage Plasmodium falciparum.

Journal: PLoS biology20110801

Title: Design, synthesis, and X-ray crystallographic studies of α-aryl substituted fosmidomycin analogues as inhibitors of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Journal: Journal of medicinal chemistry20110728

Title: Isoprene synthesis in plants: lessons from a transgenic tobacco model.

Journal: Plant, cell & environment20110601

Title: Induction of a longer term component of isoprene release in darkened aspen leaves: origin and regulation under different environmental conditions.

Journal: Plant physiology20110601

Title: A second target of the antimalarial and antibacterial agent fosmidomycin revealed by cellular metabolic profiling.

Journal: Biochemistry20110503

Title: A high-throughput screening assay for simultaneous selection of inhibitors of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate synthase (Dxs) or 1-deoxy-D-xylulose 5-phosphate reductoisomerase (Dxr).

Journal: Journal of biomolecular screening20110301

Title: Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors.

Journal: Bioorganic & medicinal chemistry20110201

Title: Fosmidomycin uptake into Plasmodium and Babesia-infected erythrocytes is facilitated by parasite-induced new permeability pathways.

Journal: PloS one20110101

Title: Isoprenoid precursor biosynthesis offers potential targets for drug discovery against diseases caused by apicomplexan parasites.

Journal: Current topics in medicinal chemistry20110101

Title: Evidence of isoprenoid precursor toxicity in Bacillus subtilis.

Journal: Bioscience, biotechnology, and biochemistry20110101

Title: Characterization and structure of DhpI, a phosphonate O-methyltransferase involved in dehydrophos biosynthesis.

Journal: Proceedings of the National Academy of Sciences of the United States of America20101012

Title: Synthesis and antiplasmodial activity of highly active reverse analogues of the antimalarial drug candidate fosmidomycin.

Journal: ChemMedChem20101004

Title: Crystal structure of 1-deoxy-d-xylulose 5-phosphate reductoisomerase from the hyperthermophile Thermotoga maritima for insights into the coordination of conformational changes and an inhibitor binding.

Journal: Journal of structural biology20100601

Title: Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase.

Journal: The Journal of organic chemistry20100521

Title: Effects of fosmidomycin on plant photosynthesis as measured by gas exchange and chlorophyll fluorescence.

Journal: Photosynthesis research20100401

Title: A high-throughput colorimetric-based bioassay method for determination of fosmidomycin in plasma and urine and application for pharmacokinetic study.

Journal: Journal of pharmacological and toxicological methods20100101

Title: The malarial drug target Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (PfDXR): development of a 3-D model for identification of novel, structural and functional features and for inhibitor screening.

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Journal: Journal of medicinal chemistry20091112

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Title: Studies addressing the importance of charge in the binding of fosmidomycin-like molecules to deoxyxylulosephosphate reductoisomerase.

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Journal: Bioorganic & medicinal chemistry20080315

Title: Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake.

Journal: BMC microbiology20080101

Title: Assessment of the pharmacokinetics and dynamics of two combination regimens of fosmidomycin-clindamycin in patients with acute uncomplicated falciparum malaria.

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Title: Synthesis and evaluation of alpha,beta-unsaturated alpha-aryl-substituted fosmidomycin analogues as DXR inhibitors.

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Title: Assessment of in vitro antimalarial interactions between dihydroartemisinin and fosmidomycin.

Journal: The Southeast Asian journal of tropical medicine and public health20070901

Title: The methylerythritol phosphate pathway for isoprenoid biosynthesis in coccidia: presence and sensitivity to fosmidomycin.

Journal: Experimental parasitology20070801

Title: An Escherichia coli undecaprenyl-pyrophosphate phosphatase implicated in undecaprenyl phosphate recycling.

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Journal: The American journal of tropical medicine and hygiene20070801

Title: Structures of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase provide new insights into catalysis.

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Title: Conformationally restrained aromatic analogues of fosmidomycin and FR900098.

Journal: Archiv der Pharmazie20070701

Title: Structure of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in a quaternary complex with a magnesium ion, NADPH and the antimalarial drug fosmidomycin.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications20070601

Title: Effect of fosmidomycin on metabolic and transcript profiles of the methylerythritol phosphate pathway in Plasmodium falciparum.

Journal: Memorias do Instituto Oswaldo Cruz20070601

Title: Divergent strategy for the synthesis of alpha-aryl-substituted fosmidomycin analogues.

Journal: The Journal of organic chemistry20070511

Title: Bioassay for determination of fosmidomycin in plasma and urine: application for pharmacokinetic dose optimisation.

Journal: Journal of microbiological methods20070401

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Journal: Malaria journal20070101

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Title: Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.

Journal: Journal of medicinal chemistry20061214

Title: Arylmethyl substituted derivatives of Fosmidomycin: synthesis and antimalarial activity.

Journal: European journal of medicinal chemistry20061201

Title: Isoprenoid biosynthesis in plants - 2C-methyl-D-erythritol-4-phosphate synthase (IspC protein) of Arabidopsis thaliana.

Journal: The FEBS journal20061001

Title: Synthesis and antimalarial activity of chain substituted pivaloyloxymethyl ester analogues of Fosmidomycin and FR900098.

Journal: Bioorganic & medicinal chemistry20060801

Title: The relationship between the methyl-erythritol phosphate pathway leading to emission of volatile isoprenoids and abscisic acid content in leaves.

Journal: Plant physiology20060801

Title: Plastid cues posttranscriptionally regulate the accumulation of key enzymes of the methylerythritol phosphate pathway in Arabidopsis.

Journal: Plant physiology20060501

Title: Involvement of 2-C-methyl-D-erythritol-4-phosphate pathway in biosynthesis of aphidicolin-like tetracyclic diterpene of Scoparia dulcis.

Journal: Chemical & pharmaceutical bulletin20060501

Title: Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors.

Journal: Journal of medicinal chemistry20060420

Title: Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Journal: Bioorganic & medicinal chemistry20060401

Title: Synthesis of alpha-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors.

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Title: A fragment-based approach to understanding inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.

Journal: Chembiochem : a European journal of chemical biology20051001

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Journal: Phytochemistry20050801

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Journal: Archiv der Pharmazie20050701

Title: AFMoC enhances predictivity of 3D QSAR: a case study with DOXP-reductoisomerase.

Journal: Journal of medicinal chemistry20050519

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Journal: Journal of medicinal chemistry20050505

Title: Isoprene decreases the concentration of nitric oxide in leaves exposed to elevated ozone.

Journal: The New phytologist20050501

Title: [Effects of fosmidomycin and lovastatin treatment on taxol biosynthesis in suspension culture cells of Taxus chinensis].

Journal: Zhi wu sheng li yu fen zi sheng wu xue xue bao = Journal of plant physiology and molecular biology20050401

Title: Isoprenoid biosynthesis as a target for antibacterial and antiparasitic drugs: phosphonohydroxamic acids as inhibitors of deoxyxylulose phosphate reducto-isomerase.

Journal: The Biochemical journal20050215

Title: The crystal structure of E.coli 1-deoxy-D-xylulose-5-phosphate reductoisomerase in a ternary complex with the antimalarial compound fosmidomycin and NADPH reveals a tight-binding closed enzyme conformation.

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Journal: Journal of enzyme inhibition and medicinal chemistry20041201

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Journal: Bioorganic & medicinal chemistry letters20041101

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Journal: The Journal of infectious diseases20041101

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