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4773-29-9,MFCD00149493
Catalog No.:AA00DDQF

4773-29-9 | N-Acetyl-d-mannosamine

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1g
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$29.00   $20.00
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5g
95%
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$45.00   $32.00
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25g
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$117.00   $82.00
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100g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DDQF
Chemical Name:
N-Acetyl-d-mannosamine
CAS Number:
4773-29-9
Molecular Formula:
C8H15NO6
Molecular Weight:
221.2078
MDL Number:
MFCD00149493
SMILES:
OCC1OC(O)C(C(C1O)O)NC(=O)C
Properties
Computed Properties
 
Complexity:
235  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
1  
XLogP3:
-1.7  

Literature

Title: Protein Sialylation Regulates a Gene Expression Signature that Promotes Breast Cancer Cell Pathogenicity.

Journal: ACS chemical biology 20160819

Title: NANS-mediated synthesis of sialic acid is required for brain and skeletal development.

Journal: Nature genetics 20160701

Title: Characterization of the sialic acid synthase from Aliivibrio salmonicida suggests a novel pathway for bacterial synthesis of 7-O-acetylated sialic acids.

Journal: Glycobiology 20130701

Title: Functional assignment of gene AAC16202.1 from Rhodobacter capsulatus SB1003: new insights into the bacterial SDR sorbitol dehydrogenases family.

Journal: Biochimie 20121101

Title: Synthesis and preliminary biological evaluation of carba analogues from Neisseria meningitidis A capsular polysaccharide.

Journal: Organic & biomolecular chemistry 20120907

Title: Metabolic monosaccharides altered cell responses to anticancer drugs.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20120601

Title: Crystal structures of N-acetylmannosamine kinase provide insights into enzyme activity and inhibition.

Journal: The Journal of biological chemistry 20120420

Title: The Gne M712T mouse as a model for human glomerulopathy.

Journal: The American journal of pathology 20120401

Title: Peracetylated N-acetylmannosamine, a synthetic sugar molecule, efficiently rescues muscle phenotype and biochemical defects in mouse model of sialic acid-deficient myopathy.

Journal: The Journal of biological chemistry 20120120

Title: N-acetylgalactosamine kinase: a naturally promiscuous small molecule kinase.

Journal: Applied biochemistry and biotechnology 20120101

Title: Metabolism of diazirine-modified N-acetylmannosamine analogues to photo-cross-linking sialosides.

Journal: Bioconjugate chemistry 20110921

Title: 2-Oxoglycosyl ('ulosyl') and 2-oximinoglycosyl bromides: versatile donors for the expedient assembly of oligosaccharides with β-D-mannose, β-L-rhamnose, N-acetyl-β-D-mannosamine, and N-acetyl-β-D-mannosaminuronic acid units.

Journal: Chemical reviews 20110914

Title: Synthesis of an antiviral drug precursor from chitin using a saprophyte as a whole-cell catalyst.

Journal: Microbial cell factories 20110101

Title: An investigation of intracellular glycosylation activities in CHO cells: effects of nucleotide sugar precursor feeding.

Journal: Biotechnology and bioengineering 20101001

Title: [Animal model of distal myopathy with rimmed vacuoles/hereditary inclusion body myopathy and preclinical trial with sugar compounds].

Journal: Brain and nerve = Shinkei kenkyu no shinpo 20100601

Title: Development of delivery methods for carbohydrate-based drugs: controlled release of biologically-active short chain fatty acid-hexosamine analogs.

Journal: Glycoconjugate journal 20100501

Title: Coupled bioconversion for preparation of N-acetyl-D: -neuraminic acid using immobilized N-acetyl-D: -glucosamine-2-epimerase and N-acetyl-D: -neuraminic acid lyase.

Journal: Applied microbiology and biotechnology 20100201

Title: Lessons from GNE-deficient embryonic stem cells: sialic acid biosynthesis is involved in proliferation and gene expression.

Journal: Glycobiology 20100101

Title: In vivo imaging of Caenorhabditis elegans glycans.

Journal: ACS chemical biology 20091218

Title: Targeting pro-invasive oncogenes with short chain fatty acid-hexosamine analogues inhibits the mobility of metastatic MDA-MB-231 breast cancer cells.

Journal: Journal of medicinal chemistry 20081225

Title: Structural elucidation of the nonclassical secondary cell wall polysaccharide from Bacillus cereus ATCC 10987. Comparison with the polysaccharides from Bacillus anthracis and B. cereus type strain ATCC 14579 reveals both unique and common structural features.

Journal: The Journal of biological chemistry 20081031

Title: A crosslinked inclusion body process for sialic acid synthesis.

Journal: Journal of biotechnology 20080320

Title: [Proteinuria: many actors but one protagonist?].

Journal: Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia 20080101

Title: Divergent evolution of function in the ROK sugar kinase superfamily: role of enzyme loops in substrate specificity.

Journal: Biochemistry 20071127

Title: [Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20071001

Title: Sizing up sialic acid in glomerular disease.

Journal: The Journal of clinical investigation 20070601

Title: Mutation in the key enzyme of sialic acid biosynthesis causes severe glomerular proteinuria and is rescued by N-acetylmannosamine.

Journal: The Journal of clinical investigation 20070601

Title: Engineering the sialic acid in organs of mice using N-propanoylmannosamine.

Journal: Biochimica et biophysica acta 20070201

Title: Purification and characterization of GlcNAc-6-P 2-epimerase from Escherichia coli K92.

Journal: Acta biochimica Polonica 20070101

Title: Targeting glycosylation pathways and the cell cycle: sugar-dependent activity of butyrate-carbohydrate cancer prodrugs.

Journal: Chemistry & biology 20061201

Title: Preparative production and separation of 2-acetamido-2-deoxymannopyranoside-containing saccharides using borate-saturated polyolic exclusion gels.

Journal: Journal of chromatography. A 20060915

Title: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor.

Journal: Chemical communications (Cambridge, England) 20060807

Title: Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology.

Journal: Nature chemical biology 20060301

Title: Giving cells a new sugar-coating.

Journal: Nature chemical biology 20060301

Title: Transport of N-acetyl-D-galactosamine in Escherichia coli K92: effect on acetyl-amino sugar metabolism and polysialic acid production.

Journal: Biochimie 20060101

Title: Synthesis of non-natural ManNAc analogs for the expression of thiols on cell-surface sialic acids.

Journal: Nature protocols 20060101

Title: Mannosamine supplementation extends the N-acetylglucosaminylation of recombinant human secreted alkaline phosphatase produced in Trichoplusia ni (cabbage looper) insect cell cultures.

Journal: Biotechnology and applied biochemistry 20050801

Title: Engineering intracellular CMP-sialic acid metabolism into insect cells and methods to enhance its generation.

Journal: Biochemistry 20050524

Title: Alpha-N-acetylmannosamine (ManNAc) synthesis via rhodium(II)-catalyzed oxidative cyclization of glucal 3-carbamates.

Journal: The Journal of organic chemistry 20050513

Title: Dynamics in the cyclic Enterobacterial common antigen as studied by 13C NMR relaxation.

Journal: Journal of biomolecular NMR 20050401

Title: Structural and mechanistic analysis of sialic acid synthase NeuB from Neisseria meningitidis in complex with Mn2+, phosphoenolpyruvate, and N-acetylmannosaminitol.

Journal: The Journal of biological chemistry 20050204

Title: Epigenetic reprogramming of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE) in HIV-1-infected CEM T cells.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20041201

Title: Characterization of N-acetylneuraminic acid synthase isoenzyme 1 from Campylobacter jejuni.

Journal: The Biochemical journal 20041001

Title: Characterization of the metabolic flux and apoptotic effects of O-hydroxyl- and N-acyl-modified N-acetylmannosamine analogs in Jurkat cells.

Journal: The Journal of biological chemistry 20040430

Title: Characterization of the cellular uptake and metabolic conversion of acetylated N-acetylmannosamine (ManNAc) analogues to sialic acids.

Journal: Biotechnology and bioengineering 20040220

Title: Establishment of N-acetylmannosamine (ManNAc) analogue-resistant cell lines as improved hosts for sialic acid engineering applications.

Journal: Biotechnology progress 20040101

Title: Engineering sialic acid synthetic ability into insect cells: identifying metabolic bottlenecks and devising strategies to overcome them.

Journal: Biochemistry 20031230

Title: Lec3 Chinese hamster ovary mutants lack UDP-N-acetylglucosamine 2-epimerase activity because of mutations in the epimerase domain of the Gne gene.

Journal: The Journal of biological chemistry 20031226

Title: The first committed step in the biosynthesis of sialic acid by Escherichia coli K1 does not involve a phosphorylated N-acetylmannosamine intermediate.

Journal: Molecular microbiology 20031101

Title: Cloning, over-expression, purification, and characterisation of N-acetylneuraminate synthase from Streptococcus agalactiae.

Journal: Protein expression and purification 20030201

Title: Proton affinity differences among three N-acetylhexosamines studied by the kinetic method.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation.

Journal: Journal of the American Chemical Society 20021218

Title: Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide.

Journal: The Journal of organic chemistry 20021018

Title: Transport of N-acetyl-D-mannosamine and N-acetyl-D-glucosamine in Escherichia coli K1: effect on capsular polysialic acid production.

Journal: FEBS letters 20020130

Title: Bacillus anthracis cell envelope components.

Journal: Current topics in microbiology and immunology 20020101

Title: Substrate specificity of the sialic acid biosynthetic pathway.

Journal: Biochemistry 20011030

Title: Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase.

Journal: Carbohydrate research 20010518

Title: Metabolic control of recombinant protein N-glycan processing in NS0 and CHO cells.

Journal: Biotechnology and bioengineering 20010505

Title: Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-D-mannose 6-phosphate: a new approach.

Journal: Carbohydrate research 20010215

Title: Biosynthesis of N-acetylneuraminic acid in cells lacking UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase.

Journal: Biological chemistry 20010201

Title: Production of a sialylated N-linked glycoprotein in insect cells.

Journal: Biotechnology progress 20010101

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