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17989-41-2,MFCD00236373
Catalog No.:AA00B64F

17989-41-2 | [R,(-)]-1-O-Phosphono-D-glycerol

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00B64F
Chemical Name:
[R,(-)]-1-O-Phosphono-D-glycerol
CAS Number:
17989-41-2
Molecular Formula:
C3H9O6P
Molecular Weight:
172.0737
MDL Number:
MFCD00236373
SMILES:
OC[C@H](COP(=O)(O)O)O
Properties
Computed Properties
 
Complexity:
129  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
-2.9  

Literature

Title: Crystal structures of triosephosphate isomerase from methicillin resistant Staphylococcus aureus MRSA252 provide structural insights into novel modes of ligand binding and unique conformations of catalytic loop.

Journal: Biochimie 20121201

Title: Triacylglycerol biosynthesis occurs via the glycerol-3-phosphate pathway in the insect Rhodnius prolixus.

Journal: Biochimica et biophysica acta 20121201

Title: Acyl-CoA:diacylglycerol acyltransferase: molecular biology, biochemistry and biotechnology.

Journal: Progress in lipid research 20121001

Title: Increased glyceride-glycerol synthesis in liver and brown adipose tissue of rat: in-vivo contribution of glycolysis and glyceroneogenesis.

Journal: Lipids 20120801

Title: One-pot four-enzyme synthesis of ketoses with fructose 1,6-bisphosphate aldolases from Staphylococcus carnosus and rabbit muscle.

Journal: Carbohydrate research 20120801

Title: Validation study of urinary metabolites as potential biomarkers for prostate cancer detection.

Journal: Bioanalysis 20120601

Title: Glycerol utilization by Rhizobium leguminosarum requires an ABC transporter and affects competition for nodulation.

Journal: Microbiology (Reading, England) 20120501

Title: FAT SIGNALS--lipases and lipolysis in lipid metabolism and signaling.

Journal: Cell metabolism 20120307

Title: Resveratrol plus ethanol counteract the ethanol-induced impairment of energy metabolism: ³¹P NMR study of ATP and sn-glycerol-3-phosphate on isolated and perfused rat liver.

Journal: Pharmacological research 20120301

Title: Metabolic characteristics of human subcutaneous abdominal adipose tissue after overnight fast.

Journal: American journal of physiology. Endocrinology and metabolism 20120215

Title: Integration of metabolomics and expression of glycerol-3-phosphate acyltransferase (GPAM) in breast cancer-link to patient survival, hormone receptor status, and metabolic profiling.

Journal: Journal of proteome research 20120203

Title: Structural and functional properties of glycerol-3-phosphate dehydrogenase from a mammalian hibernator.

Journal: The protein journal 20120201

Title: Temporal expression of bacterial proteins instructs host CD4 T cell expansion and Th17 development.

Journal: PLoS pathogens 20120101

Title: Stimulation of B7-H3 (CD276) directs the differentiation of human marrow stromal cells to osteoblasts.

Journal: Immunobiology 20111201

Title: Glycerol-3-phosphate and systemic immunity.

Journal: Plant signaling & behavior 20111101

Title: Thyroid hormone contributes to the hypolipidemic effect of polyunsaturated fatty acids from fish oil: in vivo evidence for cross talking mechanisms.

Journal: The Journal of endocrinology 20111001

Title: Glycerol 3-phosphate alters Trypanosoma brucei hexokinase activity in response to environmental change.

Journal: The Journal of biological chemistry 20110923

Title: Efficacy of a novel hydroquinone-free skin-brightening cream in patients with melasma.

Journal: Journal of cosmetic dermatology 20110901

Title: Borrelia burgdorferi requires glycerol for maximum fitness during the tick phase of the enzootic cycle.

Journal: PLoS pathogens 20110701

Title: The lipid A from Vibrio fischeri lipopolysaccharide: a unique structure bearing a phosphoglycerol moiety.

Journal: The Journal of biological chemistry 20110617

Title: Characterization of the Arabidopsis glycerophosphodiester phosphodiesterase (GDPD) family reveals a role of the plastid-localized AtGDPD1 in maintaining cellular phosphate homeostasis under phosphate starvation.

Journal: The Plant journal : for cell and molecular biology 20110601

Title: Stability of heterochiral hybrid membrane made of bacterial sn-G3P lipids and archaeal sn-G1P lipids.

Journal: Biochemistry 20110517

Title: Glycerol-3-phosphate is a critical mobile inducer of systemic immunity in plants.

Journal: Nature genetics 20110501

Title: Comparative analyses imply that the enigmatic Sigma factor 54 is a central controller of the bacterial exterior.

Journal: BMC genomics 20110101

Title: Dietary cholesterol reduces plasma triacylglycerol in apolipoprotein E-null mice: suppression of lipin-1 and -2 in the glycerol-3-phosphate pathway.

Journal: PloS one 20110101

Title: Glycerophosphate is interchangeable with inorganic phosphate in terms of safety and serum pharmacokinetics.

Journal: Pharmacology 20110101

Title: Characterizing the Escherichia coli O157:H7 proteome including protein associations with higher order assemblies.

Journal: PloS one 20110101

Title: Lipid signaling and homeostasis: PA- is better than PA-H, but what about those PIPs?

Journal: Science signaling 20101207

Title: Chronically increased glucose uptake by adipose tissue leads to lactate production and improved insulin sensitivity rather than obesity in the mouse.

Journal: Diabetologia 20101101

Title: Ablation of succinate production from glucose metabolism in the procyclic trypanosomes induces metabolic switches to the glycerol 3-phosphate/dihydroxyacetone phosphate shuttle and to proline metabolism.

Journal: The Journal of biological chemistry 20101015

Title: Metabolic and transcriptional responses of glycerolipid pathways to a perturbation of glycerol 3-phosphate metabolism in Arabidopsis.

Journal: The Journal of biological chemistry 20100723

Title: Light-driven formation and rupture of droplet bilayers.

Journal: Langmuir : the ACS journal of surfaces and colloids 20100504

Title: Atypical transcriptional regulation and role of a new toxin-antitoxin-like module and its effect on the lipid composition of Bradyrhizobium japonicum.

Journal: Molecular plant-microbe interactions : MPMI 20100501

Title: Mitochondrial ROS production correlates with, but does not directly regulate lifespan in Drosophila.

Journal: Aging 20100401

Title: Mice deficient in phosphofructokinase-M have greatly decreased fat stores.

Journal: Obesity (Silver Spring, Md.) 20100301

Title: Silymarin secretion and its elicitation by methyl jasmonate in cell cultures of Silybum marianum is mediated by phospholipase D-phosphatidic acid.

Journal: Journal of experimental botany 20100301

Title: The alpha glycerophosphate cycle in Drosophila melanogaster VI. structure and evolution of enzyme paralogs in the genus Drosophila.

Journal: The Journal of heredity 20100101

Title: The alpha glycerophosphate cycle in Drosophila melanogaster V. molecular analysis of alpha glycerophosphate dehydrogenase and alpha glycerophosphate oxidase mutants.

Journal: The Journal of heredity 20100101

Title: Characterization and partial purification of acyl-CoA:glycerol 3-phosphate acyltransferase from sunflower (Helianthus annuus L.) developing seeds.

Journal: Plant physiology and biochemistry : PPB 20100101

Title: Uncoupling protein-1 is not leaky.

Journal: Biochimica et biophysica acta 20100101

Title: sRNAscanner: a computational tool for intergenic small RNA detection in bacterial genomes.

Journal: PloS one 20100101

Title: Molecular dynamics simulation studies of GLUT4: substrate-free and substrate-induced dynamics and ATP-mediated glucose transport inhibition.

Journal: PloS one 20100101

Title: Structure of the X (ADRP) domain of nsp3 from feline coronavirus.

Journal: Acta crystallographica. Section D, Biological crystallography 20091201

Title: Cloning and characterization of a novel phytase from wastewater treatment yeast Hansenula fabianii J640 and expression in Pichia pastoris.

Journal: Journal of bioscience and bioengineering 20090901

Title: Glycerol-3-phosphate acyltransferases: rate limiting enzymes of triacylglycerol biosynthesis.

Journal: Biochimica et biophysica acta 20090601

Title: Phosphate and carbon source regulation of two PhoP-dependent glycerophosphodiester phosphodiesterase genes of Streptomyces coelicolor.

Journal: Microbiology (Reading, England) 20090601

Title: Design and synthesis of small molecule glycerol 3-phosphate acyltransferase inhibitors.

Journal: Journal of medicinal chemistry 20090528

Title: [Effects of different phosphorus substrates on the growth and phosphatase activity of Skeletonema costatum and Prorocentrum donghaiense].

Journal: Huan jing ke xue= Huanjing kexue 20090315

Title: Positively regulated glycerol/G3P-dependent Bacillus subtilis gene expression system based on anti-termination.

Journal: Journal of molecular microbiology and biotechnology 20090101

Title: Constraint-based analysis of metabolic capacity of Salmonella typhimurium during host-pathogen interaction.

Journal: BMC systems biology 20090101

Title: Brucella melitensis global gene expression study provides novel information on growth phase-specific gene regulation with potential insights for understanding Brucella:host initial interactions.

Journal: BMC microbiology 20090101

Title: The Mycoplasma conjunctivae genome sequencing, annotation and analysis.

Journal: BMC bioinformatics 20090101

Title: Diversity and evolution of the small multidrug resistance protein family.

Journal: BMC evolutionary biology 20090101

Title: The effects of ascorbic acid on homolytic processes involving alpha-hydroxyl-containing carbon-centered radicals.

Journal: Bioorganic & medicinal chemistry letters 20081215

Title: The effect of vitamin A supplementation on postnatal adipose tissue development of lambs.

Journal: Journal of animal science 20081201

Title: Involvement of PlsX and the acyl-phosphate dependent sn-glycerol-3-phosphate acyltransferase PlsY in the initial stage of glycerolipid synthesis in Bacillus subtilis.

Journal: Genes & genetic systems 20081201

Title: Glyceroneogenesis is the dominant pathway for triglyceride glycerol synthesis in vivo in the rat.

Journal: The Journal of biological chemistry 20081010

Title: [Effects of different phosphorus sources on the growth and toxin production of Prorocentrum lima].

Journal: Huan jing ke xue= Huanjing kexue 20081001

Title: Characterization of CetA and CetB, a bipartite energy taxis system in Campylobacter jejuni.

Journal: Molecular microbiology 20080901

Title: Helix dynamics in a membrane transport protein: comparative simulations of the glycerol-3-phosphate transporter and its constituent helices.

Journal: Molecular membrane biology 20080901

Title: Glycerol-3-phosphate levels are associated with basal resistance to the hemibiotrophic fungus Colletotrichum higginsianum in Arabidopsis.

Journal: Plant physiology 20080801

Title: Fermentative production of L-glycerol 3-phosphate utilizing a Saccharomyces cerevisiae strain with an engineered glycerol biosynthetic pathway.

Journal: Biotechnology and bioengineering 20080615

Title: Enzymes of glycerol and glyceraldehyde metabolism in mouse liver: effects of caloric restriction and age on activities.

Journal: Bioscience reports 20080401

Title: Structure of alpha-glycerophosphate oxidase from Streptococcus sp.: a template for the mitochondrial alpha-glycerophosphate dehydrogenase.

Journal: Biochemistry 20080122

Title: From the determination of complex reaction mechanisms to systems biology.

Journal: Annual review of biochemistry 20080101

Title: Ins and outs of major facilitator superfamily antiporters.

Journal: Annual review of microbiology 20080101

Title: Stimulation of H(2)O(2) generation by calcium in brain mitochondria respiring on alpha-glycerophosphate.

Journal: Journal of neuroscience research 20071115

Title: Glyceroneogenesis and the supply of glycerol-3-phosphate for glyceride-glycerol synthesis in liver slices of fasted and diabetic rats.

Journal: American journal of physiology. Endocrinology and metabolism 20071101

Title: Kinetic evidence is consistent with the rocker-switch mechanism of membrane transport by GlpT.

Journal: Biochemistry 20071030

Title: Effects of cell volume regulating osmolytes on glycerol 3-phosphate binding to triosephosphate isomerase.

Journal: Biochemistry 20070904

Title: Uranium biomineralization as a result of bacterial phosphatase activity: insights from bacterial isolates from a contaminated subsurface.

Journal: Environmental science & technology 20070815

Title: Increasing seed oil content in oil-seed rape (Brassica napus L.) by over-expression of a yeast glycerol-3-phosphate dehydrogenase under the control of a seed-specific promoter.

Journal: Plant biotechnology journal 20070501

Title: A thermosensitive hydrogel based on quaternized chitosan and poly(ethylene glycol) for nasal drug delivery system.

Journal: Biomaterials 20070401

Title: Characteristics of alpha-glycerophosphate-evoked H2O2 generation in brain mitochondria.

Journal: Journal of neurochemistry 20070201

Title: Quantifying the metabolic capabilities of engineered Zymomonas mobilis using linear programming analysis.

Journal: Microbial cell factories 20070101

Title: PCK1 and PCK2 as candidate diabetes and obesity genes.

Journal: Cell biochemistry and biophysics 20070101

Title: Phenotypic and transcriptional response to selection for alcohol sensitivity in Drosophila melanogaster.

Journal: Genome biology 20070101

Title: The importance of redox shuttles to pancreatic beta-cell energy metabolism and function.

Journal: Biochemical Society transactions 20061101

Title: Solution NMR and computer simulation studies of active site loop motion in triosephosphate isomerase.

Journal: Biochemistry 20060912

Title: The crystal structure of (S)-3-O-geranylgeranylglyceryl phosphate synthase reveals an ancient fold for an ancient enzyme.

Journal: The Journal of biological chemistry 20060303

Title: Neuronal and astrocytic shuttle mechanisms for cytosolic-mitochondrial transfer of reducing equivalents: current evidence and pharmacological tools.

Journal: Biochemical pharmacology 20060214

Title: Involvement of a glycerol-3-phosphate dehydrogenase in modulating the NADH/NAD+ ratio provides evidence of a mitochondrial glycerol-3-phosphate shuttle in Arabidopsis.

Journal: The Plant cell 20060201

Title: An independent non-linear latitudinal cline for the sn-glycerol-3-phosphate (alpha- Gpdh ) polymorphism of Drosophila melanogaster from eastern Australia.

Journal: Genetical research 20060201

Title: Rooting the tree of life by transition analyses.

Journal: Biology direct 20060101

Title: Synergistic effects on escape of a ligand from the closed tryptophan synthase bienzyme complex.

Journal: Biochemistry 20051227

Title: Shotgun lipidomics identifies cardiolipin depletion in diabetic myocardium linking altered substrate utilization with mitochondrial dysfunction.

Journal: Biochemistry 20051220

Title: Physiologic and pharmacologic factors influencing glyceroneogenic contribution to triacylglyceride glycerol measured by mass isotopomer distribution analysis.

Journal: The Journal of biological chemistry 20050708

Title: Mitochondrial tissue specificity of substrates utilization in rat cardiac and skeletal muscles.

Journal: Journal of cellular physiology 20050601

Title: The initial step of glycerolipid metabolism in Leishmania major promastigotes involves a single glycerol-3-phosphate acyltransferase enzyme important for the synthesis of triacylglycerol but not essential for virulence.

Journal: Molecular microbiology 20050501

Title: Hydrogen peroxide production by Mycoplasma bovis and Mycoplasma agalactiae and effect of in vitro passage on a Mycoplasma bovis strain producing high levels of H2O2.

Journal: Veterinary research communications 20050401

Title: The 120 592 bp IncF plasmid pRSB107 isolated from a sewage-treatment plant encodes nine different antibiotic-resistance determinants, two iron-acquisition systems and other putative virulence-associated functions.

Journal: Microbiology (Reading, England) 20050401

Title: Zinc causes loss of membrane potential and elevates reactive oxygen species in rat brain mitochondria.

Journal: Mitochondrion 20050201

Title: Patterns of intron sequence evolution in Drosophila are dependent upon length and GC content.

Journal: Genome biology 20050101

Title: Identification and characterization of a gene encoding human LPGAT1, an endoplasmic reticulum-associated lysophosphatidylglycerol acyltransferase.

Journal: The Journal of biological chemistry 20041231

Title: Proposal for molecular mechanism of thionins deduced from physico-chemical studies of plant toxins.

Journal: The journal of peptide research : official journal of the American Peptide Society 20041201

Title: A mathematical model for mammary fatty acid synthesis and triglyceride assembly: the role of stearoyl CoA desaturase (SCD).

Journal: The Journal of dairy research 20041101

Title: Increased levels of glycerol-3-phosphate lead to a stimulation of flux into triacylglycerol synthesis after supplying glycerol to developing seeds of Brassica napus L. in planta.

Journal: Planta 20040901

Title: Ancestral lipid biosynthesis and early membrane evolution.

Journal: Trends in biochemical sciences 20040901

Title: Conserved (CT)n.(GA)n repeats in the non-coding regions at the Gpdh locus are binding sites for the GAGA factor in drosophila melanogaster and its sibling species.

Journal: Genetica 20040501

Title: Developmental-stage-specific triacylglycerol biosynthesis, degradation and trafficking as lipid bodies in Plasmodium falciparum-infected erythrocytes.

Journal: Journal of cell science 20040315

Title: Organization and regulation of the cytosolic NADH metabolism in the yeast Saccharomyces cerevisiae.

Journal: Molecular and cellular biochemistry 20040101

Title: Some processes of energy saving and expenditure occurring during ethanol perfusion in the isolated liver of fed rats; a Nuclear Magnetic Resonance study.

Journal: BMC physiology 20040101

Title: Oxidation of glycerol-3-phosphate in porcine and bovineadrenal cortex mitochondria.

Journal: Acta biochimica Polonica 20040101

Title: Hormonal regulation of postnatal chicken preadipocyte differentiation in vitro.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20031001

Title: Structural biology. Breaching the barrier.

Journal: Science (New York, N.Y.) 20030801

Title: Structure and mechanism of the glycerol-3-phosphate transporter from Escherichia coli.

Journal: Science (New York, N.Y.) 20030801

Title: A novel colorimetric assay for the determination of lysophosphatidic acid in plasma using an enzymatic cycling method.

Journal: Clinica chimica acta; international journal of clinical chemistry 20030701

Title: Leishmania mexicana glycerol-3-phosphate dehydrogenase showed conformational changes upon binding a bi-substrate adduct.

Journal: Journal of molecular biology 20030530

Title: Purification and characterization of geranylgeranylglyceryl phosphate synthase from a thermoacidophilic archaeon, Thermoplasma acidophilum.

Journal: Journal of biochemistry 20030501

Title: Isolation and properties of cytoplasmic alpha-glycerol 3-phosphate dehydrogenase from the pectoral muscle of the fruit bat, Eidolon helvum.

Journal: Journal of biochemistry and molecular biology 20030331

Title: CTP:glycerol 3-phosphate cytidylyltransferase (TarD) from Staphylococcus aureus catalyzes the cytidylyl transfer via an ordered Bi-Bi reaction mechanism with micromolar K(m) values.

Journal: Biochimica et biophysica acta 20030321

Title: Active site loop motion in triosephosphate isomerase: T-jump relaxation spectroscopy of thermal activation.

Journal: Biochemistry 20030318

Title: Identification of a mitochondrial glycerol-3-phosphate dehydrogenase from Arabidopsis thaliana: evidence for a mitochondrial glycerol-3-phosphate shuttle in plants.

Journal: FEBS letters 20030211

Title: [Computer analysis of regulating metabolism of glycerol-3-phosphate in proteobacteria genome].

Journal: Molekuliarnaia biologiia 20030101

Title: Analysis of membrane stereochemistry with homology modeling of sn-glycerol-1-phosphate dehydrogenase.

Journal: Protein engineering 20021201

Title: Glycerophosphocholine metabolism in higher plant cells. Evidence of a new glyceryl-phosphodiester phosphodiesterase.

Journal: Plant physiology 20020901

Title: Molecular basis defining human Chlamydia trachomatis tissue tropism. A possible role for tryptophan synthase.

Journal: The Journal of biological chemistry 20020726

Title: Aerobic sn-glycerol-3-phosphate dehydrogenase from Escherichia coli binds to the cytoplasmic membrane through an amphipathic alpha-helix.

Journal: The Biochemical journal 20020715

Title: Crystal structure of the beta Ser178--> Pro mutant of tryptophan synthase. A 'knock-out' allosteric enzyme.

Journal: The Journal of biological chemistry 20020322

Title: Kinetic mechanism and order of substrate binding for sn-glycerol-3-phosphate acyltransferase from squash (Cucurbita moschata).

Journal: FEBS letters 20020313

Title: Increased fatty acid re-esterification by PEPCK overexpression in adipose tissue leads to obesity without insulin resistance.

Journal: Diabetes 20020301

Title: A single, bi-functional aquaglyceroporin in blood-stage Plasmodium falciparum malaria parasites.

Journal: The Journal of biological chemistry 20020215

Title: Antitermination by GlpP, catabolite repression via CcpA and inducer exclusion triggered by P-GlpK dephosphorylation control Bacillus subtilis glpFK expression.

Journal: Molecular microbiology 20020201

Title: Effects of modulation of glycerol kinase expression on lipid and carbohydrate metabolism in human muscle cells.

Journal: The Journal of biological chemistry 20020125

Title: Improving 1,3-propanediol production from glycerol in a metabolically engineered Escherichia coli by reducing accumulation of sn-glycerol-3-phosphate.

Journal: Biotechnology progress 20020101

Title: A novel pathway for lipid biosynthesis: the direct acylation of glycerol.

Journal: Journal of lipid research 20011201

Title: Performance of batch membrane reactor: Glycerol-3-phosphate synthesis coupled with adenosine triphosphate regeneration.

Journal: Biotechnology and bioengineering 20010820

Title: Glycerol-stimulated proinsulin biosynthesis in isolated pancreatic rat islets via adenoviral-induced expression of glycerol kinase is mediated via mitochondrial metabolism.

Journal: Diabetes 20010801

Title: Muscle glycogen, lactate and glycerol-3-phosphate concentrations of larval and young adult lampreys in response to exercise.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20010701

Title: Cloning and sequence analysis of Gpdh in Callosobruchus chinensis (Coleoptera: Bruchidae).

Journal: Molecules and cells 20010630

Title: The time scale of the catalytic loop motion in triosephosphate isomerase.

Journal: Journal of molecular biology 20010629

Title: Solution-state NMR investigations of triosephosphate isomerase active site loop motion: ligand release in relation to active site loop dynamics.

Journal: Journal of molecular biology 20010629

Title: High-yield expression and functional analysis of Escherichia coli glycerol-3-phosphate transporter.

Journal: Biochemistry 20010605

Title: Cytosolic redox metabolism in aerobic chemostat cultures of Saccharomyces cerevisiae.

Journal: Yeast (Chichester, England) 20010501

Title: Purification and characterization of thiol-reagent-sensitive glycerol-3-phosphate acyltransferase from the membrane fraction of an oleaginous fungus.

Journal: The Biochemical journal 20010415

Title: Rapid screening of H(2)O(2) production by Mycoplasma mycoides and differentiation of European subsp. mycoides SC (small colony) isolates.

Journal: Veterinary microbiology 20010226

Title: The yeast glycerol 3-phosphatases Gpp1p and Gpp2p are required for glycerol biosynthesis and differentially involved in the cellular responses to osmotic, anaerobic, and oxidative stress.

Journal: The Journal of biological chemistry 20010202

Title: Molecular and physiological characterization of the NAD-dependent glycerol 3-phosphate dehydrogenase in the filamentous fungus Aspergillus nidulans.

Journal: Molecular microbiology 20010101

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Tags:17989-41-2 Molecular Formula|17989-41-2 MDL|17989-41-2 SMILES|17989-41-2 [R,(-)]-1-O-Phosphono-D-glycerol