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496-55-9,MFCD18643039
Catalog No.:AA00DF4P

496-55-9 | D-Erythrulose

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5mg
1M in Water
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  • Technical Information
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Technical Information
Catalog Number:
AA00DF4P
Chemical Name:
D-Erythrulose
CAS Number:
496-55-9
Molecular Formula:
C4H8O4
Molecular Weight:
120.1039
MDL Number:
MFCD18643039
SMILES:
OCC(=O)[C@@H](CO)O
Properties
Computed Properties
 
Complexity:
80.1  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-2  

Literature

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Journal: Carbohydrate research 20120901

Title: Nondestructive fluorescence-based quantification of threose-induced collagen cross-linking in bovine articular cartilage.

Journal: Journal of biomedical optics 20120901

Title: Kinetic mechanism of fuculose-1-phosphate aldolase from the hyperthermophilic archaeon Methanococcus jannaschii.

Journal: Enzyme and microbial technology 20120405

Title: Heterologous expression and characterization of soluble recombinant 3-deoxy-d-arabino-heptulosonate-7-phosphate synthase from Actinosynnema pretiosum ssp. auranticum ATCC31565 through co-expression with Chaperones in Escherichia coli.

Journal: Protein expression and purification 20120401

Title: Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions.

Journal: Organic & biomolecular chemistry 20120227

Title: Structural insight into mechanism and diverse substrate selection strategy of L-ribulokinase.

Journal: Proteins 20120101

Title: The transcriptome of compatible and incompatible interactions of potato (Solanum tuberosum) with Phytophthora infestans revealed by DeepSAGE analysis.

Journal: PloS one 20120101

Title: tkt1, located on a novel pathogenicity island, is prevalent in avian and human extraintestinal pathogenic Escherichia coli.

Journal: BMC microbiology 20120101

Title: Computational study of mutarotation in erythrose and threose.

Journal: Carbohydrate research 20111227

Title: Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway.

Journal: Bioorganic & medicinal chemistry letters 20111115

Title: Vitamin C degradation products and pathways in the human lens.

Journal: The Journal of biological chemistry 20111028

Title: Computed tomography detects changes in contrast agent diffusion after collagen cross-linking typical to natural aging of articular cartilage.

Journal: Osteoarthritis and cartilage 20111001

Title: Immobilised enzyme microreactor for screening of multi-step bioconversions: characterisation of a de novo transketolase-ω-transaminase pathway to synthesise chiral amino alcohols.

Journal: Journal of biotechnology 20110920

Title: Synthesis and evaluation of dual site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase.

Journal: Bioorganic & medicinal chemistry letters 20110901

Title: Inhibitory effects of Terminalia chebula extract on glycation and endothelial cell adhesion.

Journal: Planta medica 20110701

Title: Intermediate-assisted multifunctional catalysis in the conversion of flavin to 5,6-dimethylbenzimidazole by BluB: a density functional theory study.

Journal: Journal of the American Chemical Society 20110323

Title: Microspherules from sugars in the absence of nitrogen.

Journal: Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20110201

Title: The chemical synthesis of tetrodoxin: an ongoing quest.

Journal: Marine drugs 20110101

Title: Genome-wide essential gene identification in Streptococcus sanguinis.

Journal: Scientific reports 20110101

Title: Characterization of 5-chloro-5-deoxy-D-ribose 1-dehydrogenase in chloroethylmalonyl coenzyme A biosynthesis: substrate and reaction profiling.

Journal: The Journal of biological chemistry 20101029

Title: Phosphonoxins III: synthesis of α-aminophosphonate analogs of antifungal polyoxins with anti-Giardia activity.

Journal: Organic letters 20101015

Title: Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions.

Journal: Chemical communications (Cambridge, England) 20100714

Title: Specificity and mutational analysis of the metal-dependent 3-deoxy-D-manno-octulosonate 8-phosphate synthase from Acidithiobacillus ferrooxidans.

Journal: Biochimica et biophysica acta 20100701

Title: Preliminary X-ray crystallographic analysis of the D-xylulose 5-phosphate phosphoketolase from Lactococcus lactis.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20100701

Title: Expression and validation of D-erythrulose 1-phosphate dehydrogenase from Brucella abortus: a diagnostic reagent for bovine brucellosis.

Journal: Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc 20100701

Title: Characterization and inactivation of the membrane-bound polyol dehydrogenase in Gluconobacter oxydans DSM 7145 reveals a role in meso-erythritol oxidation.

Journal: Microbiology (Reading, England) 20100601

Title: Kinetic characterization and comparison of various protein crosslinking reagents for matrix modification.

Journal: Journal of materials science. Materials in medicine 20100401

Title: Methyl 5-O-(4-chloro-benzo-yl)-2-de-oxy-3-O-methyl-sulfonyl-threo-pentofuran-oside.

Journal: Acta crystallographica. Section E, Structure reports online 20100401

Title: Genome sequence of the pea aphid Acyrthosiphon pisum.

Journal: PLoS biology 20100201

Title: Molecular cloning and biochemical characterization of a novel erythrose reductase from Candida magnoliae JH110.

Journal: Microbial cell factories 20100101

Title: Abstracts of the 2008 ISSOL Meeting. August 24-29, 2008. Florence, Italy.

Journal: Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20090801

Title: Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides.

Journal: The Journal of biological chemistry 20090619

Title: D-fructose-6-phosphate aldolase in organic synthesis: cascade chemical-enzymatic preparation of sugar-related polyhydroxylated compounds.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: Enzymatic primer-extension with glycerol-nucleoside triphosphates on DNA templates.

Journal: PloS one 20090101

Title: Metabolic engineering for improving anthranilate synthesis from glucose in Escherichia coli.

Journal: Microbial cell factories 20090101

Title: Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism.

Journal: BMC microbiology 20090101

Title: A serum metabolomic investigation on hepatocellular carcinoma patients by chemical derivatization followed by gas chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20081001

Title: Quantification of kinetics for enzyme-catalysed reactions: implications for diffusional limitations at the 10 ml scale.

Journal: Biotechnology letters 20080601

Title: A new erythrose 4-phosphate dehydrogenase coupled assay for transketolase.

Journal: Journal of biochemical and biophysical methods 20080424

Title: Diastereoselective synthesis of piperidine imino sugars using aldol additions of metalated bislactim ethers to threose and erythrose acetonides.

Journal: The Journal of organic chemistry 20080321

Title: Aldol reactions between L-erythrulose derivatives and chiral alpha-amino and alpha-fluoro aldehydes: competition between Felkin-Anh and Cornforth transition states.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

Title: Glucose uptake and its effect on gene expression in prochlorococcus.

Journal: PloS one 20080101

Title: Beneficial effect of internal hydrogen bonding interactions on the beta-fragmentation of primary alkoxyl radicals. Two-step conversion of D-xylo- and D-ribofuranoses into L-threose and D-erythrose, respectively.

Journal: The Journal of organic chemistry 20071026

Title: On the basics of carbohydrate-metal chemistry: complexes of palladium(II) with hydroxyaldehyde and -ketone hydrates.

Journal: Carbohydrate research 20070813

Title: Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine.

Journal: Archives of biochemistry and biophysics 20070701

Title: Directed evolution of 2-keto-3-deoxy-6-phosphogalactonate aldolase to replace 3-deoxy-D-arabino-heptulosonic acid 7-phosphate synthase.

Journal: Journal of the American Chemical Society 20070516

Title: BluB cannibalizes flavin to form the lower ligand of vitamin B12.

Journal: Nature 20070322

Title: Photosensitizing activity of advanced glycation endproducts on tryptophan, glucose 6-phosphate dehydrogenase, human serum albumin and ascorbic acid evaluated at low oxygen pressure.

Journal: Photochemistry and photobiology 20070101

Title: Isotopic criteria in the characterization of aromatic molecules. 1. Hydrogen affiliation in natural benzenoid/phenylpropanoid molecules.

Journal: Journal of agricultural and food chemistry 20061227

Title: A re-investigation of the path of carbon in photosynthesis utilizing GC/MS methodology. Unequivocal verification of the participation of octulose phosphates in the pathway.

Journal: Photosynthesis research 20061101

Title: Generation of an antibody specific to erythritol, a non-immunogenic food additive.

Journal: Food additives and contaminants 20060901

Title: Hep27, a member of the short-chain dehydrogenase/reductase family, is an NADPH-dependent dicarbonyl reductase expressed in vascular endothelial tissue.

Journal: Cellular and molecular life sciences : CMLS 20060501

Title: Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence.

Journal: Arthritis research & therapy 20060101

Title: Systematic assignment of thermodynamic constraints in metabolic network models.

Journal: BMC bioinformatics 20060101

Title: Mariner mutagenesis of Brucella melitensis reveals genes with previously uncharacterized roles in virulence and survival.

Journal: BMC microbiology 20060101

Title: Mechanistic divergence of two closely related aldol-like enzyme-catalysed reactions.

Journal: Organic & biomolecular chemistry 20051121

Title: Bacillus subtilis 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase revisited: resolution of two long-standing enigmas.

Journal: The Biochemical journal 20050901

Title: Characterization of a recombinant type II 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Helicobacter pylori.

Journal: The Biochemical journal 20050815

Title: Primary structure analysis and functional expression of erythrose reductases from erythritol-producing fungi (Trichosporonoides megachiliensis SNG-42).

Journal: Bioscience, biotechnology, and biochemistry 20050501

Title: Alfred Werner's inorganic counterparts of racemic and mesomeric tartaric acid: a milestone revisited.

Journal: Inorganic chemistry 20041004

Title: Formation of 3-hexuloses in aldol reactions, analysis of the products as their O-isopropylidene derivatives by GC-MS.

Journal: Carbohydrate research 20040913

Title: Novel reactions of L-rhamnose isomerase from Pseudomonas stutzeri and its relation with D-xylose isomerase via substrate specificity.

Journal: Biochimica et biophysica acta 20040906

Title: Selective derivatization and sequestration of ribose from a prebiotic mix.

Journal: Journal of the American Chemical Society 20040811

Title: Zinc-proline catalyzed pathway for the formation of sugars.

Journal: Chemical communications (Cambridge, England) 20040707

Title: Base-pairing systems related to TNA containing phosphoramidate linkages: synthesis of building blocks and pairing properties.

Journal: Chemistry & biodiversity 20040701

Title: Carbohydrate carbonyl mobility--the key process in the formation of alpha-dicarbonyl intermediates.

Journal: Carbohydrate research 20040622

Title: Creation of a shikimate pathway variant.

Journal: Journal of the American Chemical Society 20040609

Title: Substrate and metal complexes of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Saccharomyces cerevisiae provide new insights into the catalytic mechanism.

Journal: Journal of molecular biology 20040326

Title: Stereoselective anti aldol reactions of erythrulose derivatives. Functionalized chiral d3 and d4 synthons.

Journal: The Journal of organic chemistry 20040319

Title: Influence of threose nucleoside units on the catalytic activity of a hammerhead ribozyme.

Journal: Chemistry & biodiversity 20040101

Title: Thermotoga maritima 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthase: the ancestral eubacterial DAHP synthase?

Journal: The Journal of biological chemistry 20030725

Title: The economical synthesis of [2'-(13)C, 1,3-(15)N2]uridine; preliminary conformational studies by solid state NMR.

Journal: Organic & biomolecular chemistry 20030621

Title: Mechanistic insight into 3-deoxy-D-manno-octulosonate-8-phosphate synthase and 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase utilizing phosphorylated monosaccharide analogues.

Journal: Biochemistry 20030506

Title: The high-resolution structure of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase reveals a twist in the plane of bound phosphoenolpyruvate.

Journal: Biochemistry 20030408

Title: Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine.

Journal: Biochimica et biophysica acta 20030317

Title: New developments in oxidative fermentation.

Journal: Applied microbiology and biotechnology 20030201

Title: Crystal structure of a B-form DNA duplex containing (L)-alpha-threofuranosyl (3'-->2') nucleosides: a four-carbon sugar is easily accommodated into the backbone of DNA.

Journal: Journal of the American Chemical Society 20021120

Title: Stereoselective synthesis of (+)-boronolide.

Journal: The Journal of organic chemistry 20020906

Title: Cloning and sequence analysis of D-erythrulose reductase from chicken: its close structural relation to tetrameric carbonyl reductases.

Journal: Protein engineering 20020701

Title: L-erythrulose production by oxidative fermentation is catalyzed by PQQ-containing membrane-bound dehydrogenase.

Journal: Bioscience, biotechnology, and biochemistry 20020201

Title: Biosynthesis of 1-deoxy-1-imino-D-erythrose 4-phosphate: a defining metabolite in the aminoshikimate pathway.

Journal: Journal of the American Chemical Society 20020130

Title: Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis.

Journal: Arthritis and rheumatism 20020101

Title: Accumulation of advanced glycation endproducts reduces chondrocyte-mediated extracellular matrix turnover in human articular cartilage.

Journal: Osteoarthritis and cartilage 20011101

Title: Novel reversion reaction of D-arabino-hexose phenylosotriazole. A useful model in natural glycoside and polysaccharide analysis.

Journal: Nucleosides, nucleotides & nucleic acids 20010901

Title: Cleaving of ketosubstrates by transketolase and the nature of the products formed.

Journal: Biochemistry. Biokhimiia 20010801

Title: Inhibitors of advanced glycation end product-associated protein cross-linking.

Journal: Biochimica et biophysica acta 20010214

Title: One-substrate transketolase-catalyzed reaction.

Journal: Biochemical and biophysical research communications 20010126

Title: Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase does not catalyze the formation of the ribo analogue.

Journal: Organic letters 20010111

Title: The sugar model: catalysis by amines and amino acid products.

Journal: Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20010101

Title: A metabolic node in action: chorismate-utilizing enzymes in microorganisms.

Journal: Critical reviews in microbiology 20010101

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Tags:496-55-9 Molecular Formula|496-55-9 MDL|496-55-9 SMILES|496-55-9 D-Erythrulose