L-erythrulose
L-glycero-tetrulose
Identification
| Name | L-erythrulose |
| IUPAC | (3S)-1,3,4-trihydroxybutan-2-one |
| CAS Number | 533-50-6 |
| FDA UNII | WKK1W5B83O |
| Molecular Formula | C4 H8 O4 |
| Molecular Weight | 120.10456000 |
| MDL Number | MFCD00004703 |
| Nikkaji Number | J15.073H |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 3.003e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for L-erythrulose usage levels up to | not for fragrance use. |
| Recommendation for L-erythrulose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2-
butanone, 1,3,4-trihydroxy-, (3S)-
L-(+)-
erythrulose
laevo-
erythrulose
L-
glycero-tetrulose
(3S)-1,3,4-
trihydroxy-2-butanone
(3S)-1,3,4-
trihydroxybutan-2-one
PubMed:
Transketolase A from E. coli Significantly Suppresses Protein Glycation by Glycolaldehyde and Glyoxal in Vitro.
PubMed:
[Self-tanning and sunless tanning products].
PubMed:
New inducible promoter for gene expression and synthetic biology in Yarrowia lipolytica.
PubMed:
Identification and characterization of EYK1, a key gene for erythritol catabolism in Yarrowia lipolytica.
PubMed:
EYK1 encoding erythrulose kinase as a catabolic selectable marker for genome editing in the non-conventional yeast Yarrowia lipolytica.
PubMed:
Enhancing erythritol productivity in Yarrowia lipolytica using metabolic engineering.
PubMed:
TM0416, a Hyperthermophilic Promiscuous Nonphosphorylated Sugar Isomerase, Catalyzes Various C5 and C6 Epimerization Reactions.
PubMed:
Thiamine biosensor based on oxidative trapping of enzyme-substrate intermediate.
PubMed:
Identification of Kynoxazine, a Novel Fluorescent Product of the Reaction between 3-Hydroxykynurenine and Erythrulose in the Human Lens, and Its Role in Protein Modification.
PubMed:
Multi-step biocatalytic strategies for chiral amino alcohol synthesis.
PubMed:
An efficient amperometric transketolase assay: towards inhibitor screening.
PubMed:
Microfluidic multi-input reactor for biocatalytic synthesis using transketolase.
PubMed:
Microscale methods to rapidly evaluate bioprocess options for increasing bioconversion yields: application to the Ï-transaminase synthesis of chiral amines.
PubMed:
Characterization and multi-step transketolase-Ï-transaminase bioconversions in an immobilized enzyme microreactor (IEMR) with packed tube.
PubMed:
Chemoselective Pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies.
PubMed:
DXP reductoisomerase: reaction of the substrate in pieces reveals a catalytic role for the nonreacting phosphodianion group.
PubMed:
[Simultaneous determination of meso-erythritol and L-erythrulose in fermentation broth using high performance liquid chromatography].
PubMed:
Exploring inhibition of Pdx1, a component of the PLP synthase complex of the human malaria parasite Plasmodium falciparum.
PubMed:
Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an L-erythrulose derivative and chiral aldehydes.
PubMed:
Structural insight into mechanism and diverse substrate selection strategy of L-ribulokinase.
PubMed:
Vitamin C degradation products and pathways in the human lens.
PubMed:
Immobilised enzyme microreactor for screening of multi-step bioconversions: characterisation of a de novo transketolase-Ï-transaminase pathway to synthesise chiral amino alcohols.
PubMed:
Expression and validation of D-erythrulose 1-phosphate dehydrogenase from Brucella abortus: a diagnostic reagent for bovine brucellosis.
PubMed:
Characterization and inactivation of the membrane-bound polyol dehydrogenase in Gluconobacter oxydans DSM 7145 reveals a role in meso-erythritol oxidation.
PubMed:
Design and characterization of a prototype enzyme microreactor: quantification of immobilized transketolase kinetics.
PubMed:
Erythritol is a sweet antioxidant.
PubMed:
Aldol reactions between L-erythrulose derivatives and chiral alpha-amino and alpha-fluoro aldehydes: competition between Felkin-Anh and Cornforth transition states.
PubMed:
Boron based separations for in situ recovery of L-erythrulose from transketolase-catalyzed condensation.
PubMed:
Development of an in vitro efficacy test for self-tanning formulations.
PubMed:
Quantification of kinetics for enzyme-catalysed reactions: implications for diffusional limitations at the 10 ml scale.
PubMed:
Cloning, expression, and transcription analysis of L-arabinose isomerase gene from Mycobacterium smegmatis SMDU.
PubMed:
Glycation by ascorbic acid oxidation products leads to the aggregation of lens proteins.
PubMed:
Directed evolution of transketolase activity on non-phosphorylated substrates.
PubMed:
On the basics of carbohydrate-metal chemistry: complexes of palladium(II) with hydroxyaldehyde and -ketone hydrates.
PubMed:
Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine.
PubMed:
Vitamin C. Biosynthesis, recycling and degradation in mammals.
PubMed:
Stereoselective synthesis of the glycosidase inhibitor australine through a one-pot, double-cyclization strategy.
PubMed:
One-pot synthesis of amino-alcohols using a de-novo transketolase and beta-alanine: pyruvate transaminase pathway in Escherichia coli.
PubMed:
Flavin adenine dinucleotide-dependent 4-phospho-D-erythronate dehydrogenase is responsible for the 4-phosphohydroxy-L-threonine pathway in vitamin B6 biosynthesis in Sinorhizobium meliloti.
PubMed:
Identification of enzyme responsible for erythritol utilization and reaction product in yeast Lipomyces starkeyi.
PubMed:
Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between chiral aldehydes and a chiral ethyl ketone derived from L-erythrulose. synthesis of a C1-C9 fragment of the structure of the antifungal metabolite soraphen A1alpha.
PubMed:
Production of L-erythrose via L-erythrulose from erythritol using microbial and enzymatic reactions.
PubMed:
Evaluation of Brucella abortus S19 vaccine strains by bacteriological tests, molecular analysis of ery loci and virulence in BALB/c mice.
PubMed:
Topical delivery of retinyl ascorbate: 4. Comparative anti-oxidant activity towards DPPH.
PubMed:
Plant ribulosamine/erythrulosamine 3-kinase, a putative protein-repair enzyme.
PubMed:
Stereoselective synthesis of the naturally occurring styryllactones (+)-goniofufurone and (+)-cardiobutanolide.
PubMed:
Separation and detection of oxidation products of fluorodeoxyglucose and glucose by high-performance liquid chromatography-electrospray ionisation mass spectrometry.
PubMed:
Stereoselective anti aldol reactions of erythrulose derivatives. Functionalized chiral d3 and d4 synthons.
PubMed:
Characterization and detection of lysine-arginine cross-links derived from dehydroascorbic acid.
PubMed:
A hitherto unknown transketolase-catalyzed reaction.
PubMed:
Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between L-erythrulose derivatives and chiral aldehydes. The Felkin-Anh versus Cornforth dichotomy.
PubMed:
Modeling of reaction kinetics for reactor selection in the case of L-erythrulose synthesis.
PubMed:
New quinoproteins in oxidative fermentation.
PubMed:
New developments in oxidative fermentation.
PubMed:
Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine.
PubMed:
Stereoselective synthesis of (+)-boronolide.
PubMed:
Cloning and sequence analysis of D-erythrulose reductase from chicken: its close structural relation to tetrameric carbonyl reductases.
PubMed:
L-erythrulose production by oxidative fermentation is catalyzed by PQQ-containing membrane-bound dehydrogenase.
PubMed:
Substrate specificity and kinetic mechanism of Escherichia coli ribulokinase.
PubMed:
Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives.
PubMed:
Cleaving of ketosubstrates by transketolase and the nature of the products formed.
PubMed:
The sugar model: catalysis by amines and amino acid products.
PubMed:
One-substrate transketolase-catalyzed reaction.
PubMed:
Stereoselective 1,3-dipolar cycloadditions of a chiral nitrone derived from erythrulose. An experimental and DFT theoretical study
PubMed:
The non-oxidative degradation of ascorbic acid at physiological conditions.
PubMed:
The genes for erythritol catabolism are organized as an inducible operon in Brucella abortus.
PubMed:
D-erythrulose reductase can also reduce diacetyl: further purification and characterization of D-erythrulose reductase from chicken liver.
PubMed:
In situ product removal from E. coli transketolase-catalyzed biotransformations.
PubMed:
Purification and Some Properties of an Erythrose Reductase from an Aureobasidium sp. Mutant.
PubMed:
Slow reversible inhibition of rabbit muscle aldolase by D-erythrulose 1-phosphate.
PubMed:
Mechanism of enzymic isomerization and epimerization of D-erythrose 4-phosphate.
PubMed:
Methods for enzymatic and colorimetric determinations of D-erythrulose (D-tetrulose).
PubMed:
Characterization of an enzyme which catalyzes isomerization and epimerization of D-erythrose 4-phosphate.
PubMed:
Enzymatic isomerization and epimerization of D-erythrose 4-phosphate and its quantitative analysis by gas chromatography/mass spectrometry.
PubMed:
D-Erythrulose reductase from beef liver.
PubMed:
Studies on D-tetrose metabolism. Crystallization and properties of D-erythrulose reductase from chicken liver.
PubMed:
Effect of NADP+ and its analogs on the Rose Bengal-sensitized photoinactivation of D-erythrulose reductase from beef liver.
PubMed:
Inhibition of growth by erythritol catabolism in Brucella abortus.
PubMed:
Studies on D-tetrose metabolism. VI. Crystallization and some properties of D-erythrulose reducatase from beef liver.
PubMed:
Erythritol catabolism by Brucella abortus.
PubMed:
Studies on D-tetrose metabolism. IV. Purification and some properties of D-erythrulose reductase from beef liver.
PubMed:
Studies on D-tetrose metabolism. V. Identification of protecting factor against cold inactivation of D-erythrulose reductase from beef liver.
PubMed:
Erythritol metabolism in wild-type and mutant strains of Schizophyllum commune.
PubMed:
Erythritol metabolism by Propionibacterium pentosaceum. The role of L-erythrulose 1-phosphate.
PubMed:
STUDIES ON D-TETROSE METABOLISM. I. PURIFICATION OF D-ERYTHROSE AND PREPARATION OF D-ERYTHRULOSE.
PubMed:
D-GLYCERO-TETRULOSE 1,4-DIPHOSPHATE (D-ERYTHRULOSE 1,4-DIPHOSPHATE).
PubMed:
THE SYNTHESIS OF L-GLYCERO-TETRULOSE 1-PHOSPHATE (L-ERYTHRULOSE 1-PHOSPHATE).
PubMed:
Biochemistry of the Ustilaginales. 14. Bioassimilation of L-erythrulose into 4-0-beta-D-mannopyranosyl-D-erythritol.
PubMed:
[Formation of erythrulose from hydroxypyruvate by yeast enzymes].
PubMed:
The fermentation of L-erythrulose by Aerobacter aerogenes.
PubMed:
Mechanism of formation of erythrulose-1-phosphate by phosphoketotetrose aldolase of rat liver.
PubMed:
Synthesis of erythrulose phosphate by a soluble enzyme from rat liver.