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6322-07-2 | D-Gulono-γ-lactone
CAS No: 6322-07-2 Catalog No: AG003A7O MDL No:MFCD00005391
Product Description
Catalog Number:
AG003A7O
Chemical Name:
D-Gulono-γ-lactone
CAS Number:
6322-07-2
Molecular Formula:
C6H10O6
Molecular Weight:
178.1400
MDL Number:
MFCD00005391
IUPAC Name:
(3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
InChI:
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m1/s1
InChI Key:
SXZYCXMUPBBULW-LECHCGJUSA-N
SMILES:
OC[C@H]([C@@H]1OC(=O)[C@@H]([C@@H]1O)O)O
EC Number:
228-678-5
Properties
Complexity:
181
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
178.048g/mol
Formal Charge:
0
Heavy Atom Count:
12
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
178.14g/mol
Monoisotopic Mass:
178.048g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
107A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2
Literature
| Title | Journal |
|---|---|
| Pancreatic insulin release in vitamin C-deficient senescence marker protein-30/gluconolactonase knockout mice. | Journal of clinical biochemistry and nutrition 20120301 |
| The analysis of vitamin C concentration in organs of gulo(-/-) mice upon vitamin C withdrawal. | Immune network 20120201 |
| Antioxidant defence of colostrum and milk in consecutive lactations in sows. | Irish veterinary journal 20120101 |
| The genetics of vitamin C loss in vertebrates. | Current genomics 20110801 |
| The transcription of l-gulono-gamma-lactone oxidase, a key enzyme for biosynthesis of ascorbate, during development of Persian sturgeon Acipenser persicus. | Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20110401 |
| Suppression of CFTR-mediated Cl secretion of airway epithelium in vitamin C-deficient mice. | Journal of Korean medical science 20110301 |
| Intravenous ascorbic acid to prevent and treat cancer-associated sepsis? | Journal of translational medicine 20110101 |
| Effects of ovariectomy and ascorbic acid supplement on oxidative stress parameters and bone mineral density in rats. | The Libyan journal of medicine 20110101 |
| Recent loss of vitamin C biosynthesis ability in bats. | PloS one 20110101 |
| Pathophysiological significance of senescence marker protein-30. | Geriatrics & gerontology international 20100701 |
| In vitro antioxidant and in vivo prophylactic effects of two gamma-lactones isolated from Grewia tiliaefolia against hepatotoxicity in carbon tetrachloride intoxicated rats. | European journal of pharmacology 20100410 |
| Identification and analysis of unitary pseudogenes: historic and contemporary gene losses in humans and other primates. | Genome biology 20100101 |
| Evidence for the possible existence of a remnant L-gulono-gamma-lactone oxidase (GULO) gene in a teleost genome. | Folia biologica 20100101 |
| Vitamin C deficiency fails to protect mice from malaria. | Experimental animals 20100101 |
| Markers of oxidative stress in erythrocytes and plasma during aging in humans. | Oxidative medicine and cellular longevity 20100101 |
| Modulation of ascorbic acid metabolism by cytochrome P450 induction revealed by metabonomics and transcriptional profiling. | Magnetic resonance in chemistry : MRC 20091201 |
| Design and synthesis of N(6)-substituted-4'-thioadenosine-5'-uronamides as potent and selective human A(3) adenosine receptor agonists. | Bioorganic & medicinal chemistry 20091201 |
| Multiresidue determination of 11 new fungicides in grapes and wines by liquid-liquid extraction/clean-up and programmable temperature vaporization injection with analyte protectants/gas chromatography/ion trap mass spectrometry. | Journal of chromatography. A 20090807 |
| Use of spermine and thiabendazole as analyte protectants to improve direct analysis of 16 carbamates by gas chromatography-mass spectrometry in green vegetable matrices. | Analytical and bioanalytical chemistry 20090601 |
| L-Ascorbate biosynthesis in peach: cloning of six L-galactose pathway-related genes and their expression during peach fruit development. | Physiologia plantarum 20090601 |
| In vivo wound healing activity of the methanolic extract and its isolated constituent, gulonic acid gamma-lactone, obtained from Grewia tiliaefolia. | Planta medica 20090401 |
| Reconstruction of metabolic pathways for the cattle genome. | BMC systems biology 20090101 |
| MouseCyc: a curated biochemical pathways database for the laboratory mouse. | Genome biology 20090101 |
| Intraluminal hydrogen peroxide induces a permeability change of the endoplasmic reticulum membrane. | FEBS letters 20081224 |
| Restoration of vitamin C synthesis in transgenic Gulo-/- mice by helper-dependent adenovirus-based expression of gulonolactone oxidase. | Human gene therapy 20081201 |
| Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists. | Journal of medicinal chemistry 20081023 |
| Elevated oxidative stress and sensorimotor deficits but normal cognition in mice that cannot synthesize ascorbic acid. | Journal of neurochemistry 20080801 |
| Synthesis of 2-alkynyl substituted 4'-thioadenosine derivatives and their binding affinities at the adenosine receptors. | Archives of pharmacal research 20080801 |
| Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants. | Journal of chromatography. A 20080704 |
| Stereoselective synthesis and conformational study of novel 2',3'-Didehydro-2',3'-dideoxy-4'-selenonucleosides. | The Journal of organic chemistry 20080606 |
| Vitamin C supplementation does not protect L-gulono-gamma-lactone oxidase-deficient mice from Helicobacter pylori-induced gastritis and gastric premalignancy. | International journal of cancer 20080301 |
| Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-N,N-dialkyluronamides as human A3 adenosine receptor antagonists. | Bioorganic & medicinal chemistry letters 20080301 |
| Ascorbic acid alleviates pancreatic damage induced by dibutyltin dichloride (DBTC) in rats. | Yonsei medical journal 20071231 |
| Comparative genomics search for losses of long-established genes on the human lineage. | PLoS computational biology 20071201 |
| Effect of Docosahexaenoic Acid Ingestion on Temporal Change in Urinary Excretion of Mercapturic Acid in ODS Rats. | Journal of clinical biochemistry and nutrition 20071101 |
| Isolation and characterization of cDNA sequences of L-gulono-gamma-lactone oxidase, a key enzyme for biosynthesis of ascorbic acid, from extant primitive fish groups. | Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20070601 |
| Ascorbate deficiency results in impaired neutrophil apoptosis and clearance and is associated with up-regulation of hypoxia-inducible factor 1alpha. | Journal of leukocyte biology 20070501 |
| Sparing effects of selenium and ascorbic acid on vitamin C and E in guinea pig tissues. | Nutrition journal 20070101 |
| Design, synthesis, and anti-tumor activity of 4'-thionucleosides as potent and selective agonists at the human A3 adenosine receptor. | Nucleosides, nucleotides & nucleic acids 20070101 |
| Stereoselective functionalization of the 1'-position of 4'-thionucleosides. | Organic letters 20060914 |
| Design, synthesis, and biological activity of N6-substituted-4'-thioadenosines at the human A3 adenosine receptor. | Bioorganic & medicinal chemistry 20060715 |
| Ascorbic acid synthesis due to L-gulono-1,4-lactone oxidase expression enhances NO production in endothelial cells. | Biochemical and biophysical research communications 20060714 |
| Vitamin C fails to protect amino acids and lipids from oxidation during acute inflammation. | Free radical biology & medicine 20060501 |
| Combination of analyte protectants to overcome matrix effects in routine GC analysis of pesticide residues in food matrixes. | Analytical chemistry 20051215 |
| Determination of pesticide residues by GC-MS using analyte protectants to counteract the matrix effect. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20051101 |
| A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid. | The Journal of organic chemistry 20050819 |
| D-4'-thioadenosine derivatives as highly potent and selective agonists at the human A3 adenosine receptor. | Nucleosides, nucleotides & nucleic acids 20050101 |
| Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of alpha-glucosidases than the enantiomeric natural product DMDP. | Chemical communications (Cambridge, England) 20040907 |
| Functional rescue of vitamin C synthesis deficiency in human cells using adenoviral-based expression of murine l-gulono-gamma-lactone oxidase. | Genomics 20040301 |
| Synthesis of all four stereoisomers of 3-amino-2-hydroxybutanoic acids. | Bioscience, biotechnology, and biochemistry 20040301 |
| Developmental aspects and factors influencing the synthesis and status of ascorbic Acid in the pig. | Annual review of nutrition 20040101 |
| The whole structure of the human nonfunctional L-gulono-gamma-lactone oxidase gene--the gene responsible for scurvy--and the evolution of repetitive sequences thereon. | Journal of nutritional science and vitaminology 20031001 |
| N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor. | Journal of medicinal chemistry 20030828 |
| D-Gulonolactone as a synthon for L-noviose: first preparation of 4-O-demethyl-L-noviofuranose and related derivatives. | Organic letters 20030724 |
| Modification of analytical procedures for determining vitamin C enzyme (L-gulonolactone oxidase) activity in swine liver. | The Journal of nutritional biochemistry 20030301 |
| Impaired ascorbic acid metabolism in streptozotocin-induced diabetic rats. | Free radical biology & medicine 20021101 |
| The human L-threonine 3-dehydrogenase gene is an expressed pseudogene. | BMC genetics 20020101 |
| A newly established strain of spontaneously hypertensive rat with a defect of ascorbic acid biosynthesis. | Life sciences 20010907 |
| Synthesis of ascorbate and urate in the ovary of water buffalo. | Free radical research 20010901 |
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