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533-49-3 , L-Erythrose, CAS:533-49-3

533-49-3, L-Erythrose,
CAS:533-49-3
C4H8O4 / 120.1
MFCD00064377

L-赤藓糖, L-Erythrose

L-Erythrose is a monosaccharide that contains an hydroxyl group on the second carbon atom. It can be synthesized by a synthetic scheme involving glycolaldehyde and hydroxylamine. L-Erythrose has been shown to inhibit the enzyme phosphoglycerate kinase, which converts 2-phosphoglycerate into phosphoenolpyruvate. L-Erythrose has also been shown to inhibit dehydroascorbic acid reductase, which converts dehydroascorbic acid into ascorbic acid, and galactitol reductase, which converts galactitol into D-tagatose. The mutant strain of Escherichia coli K12 that was engineered to produce L-erythrose showed a decreased susceptibility to phage infection and an increased resistance to oxidative stress. In addition, the polyol pathway in E. coli was induced by L-erythrose treatment.


L-(+)-Erythrose is an aldotetrose carbohydrate that has been used in glycation studies and to characterize erythrose reductase activity.

L(+)-Erythrose, an aldotetrose rare sugar, may be used in glycation studies and as a reference compound in tetrose carbohydrate separation and quantitation analysis. It may be used to help identify and characterize erythrose reductase(s) and to study the mechanisms of mutarotation in monosugars. L-Erythrose may be used as a reference compound in sugar metabolism analysis.

A rare aldotetrose, L-erythrose, was produced from erythritol via a two-step reaction. In the first step, complete oxidation of erythritol to L-erythrulose was achieved by using Gluconobacter frateurii IFO 3254.

Title: L-Erythrose

CAS Registry Number: 533-49-3

CAS Name: (2S,3S)-2,3,4-Trihydroxybutanal

Molecular Formula: C4H8O4

Molecular Weight: 120.10

Percent Composition: C 40.00%, H 6.71%, O 53.29%

Literature References: From calcium L-arabonate by oxidation with H2O2: Ruff, Meusser, Ber. 34, 1365 (1901). From L-arabinose oxime: Wohl, Ber. 32, 3667 (1899). From L-arabonamide by treatment with alkaline NaOCl: Weerman, Rec. Trav. Chim. 37, 35 (1918).

Properties: Syrup. Sweet taste. Shows mutarotation. [a]D24 +11.5° (8 min) ® +15.2° (120 min) ® +30.5° (final, c = 3): Felton, Freudenberg, J. Am. Chem. Soc. 57, 1640 (1935). Soluble in water. Heating with HCl yields lactic acid. Oxidation with Br converts it to L-erythronic acid. Reduces Fehling's soln slowly in the cold. Not fermented by yeast.

Optical Rotation: [a]D24 +11.5° (8 min) ® +15.2° (120 min) ® +30.5° (final, c = 3): Felton, Freudenberg, J. Am. Chem. Soc. 57, 1640 (1935)

 

Derivative Type: Phenylosazone

Molecular Formula: C16H18N4O2

Molecular Weight: 298.34

Percent Composition: C 64.41%, H 6.08%, N 18.78%, O 10.73%

Properties: mp 164°.

Melting point: mp 164°

CAS Number533-49-3
Product NameL-Erythrose
IUPAC Name(2S,3S)-2,3,4-trihydroxybutanal
Molecular FormulaC4H8O4
Molecular Weight120.1 g/mol
InChIInChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m1/s1
InChI KeyYTBSYETUWUMLBZ-DMTCNVIQSA-N
SMILESC(C(C(C=O)O)O)O
SolubilitySoluble in DMSO
SynonymsL-Erythrose; L-(+)-Erythrose;
Canonical SMILESC(C(C(C=O)O)O)O
Isomeric SMILESC([C@@H]([C@@H](C=O)O)O)O


CAS No: 533-49-3 MDL No: MFCD00064377 Chemical Formula: C4H8O4 Molecular Weight: 120.1

COA:

NameL-Erythrose CAS: 533-49-3 F.M.: C4H8O4 M.W.: 120.1   Batch No: 20140609   Quantity:9.5g

Items

Standards

Results

Appearance

Clear and slightly yellow syrup

Complies

Solubility

Insoluble in ether, easily soluble in water

Complies

NMR and MS

Should comply

Complies

13C-NMR

Approx 93% of the total signals are fromErythrose

Complies

Assay

About 40%

Complies

Reference:

1. Rahman M, Takeshita K, Moshino H, Takada G, Izumori K, J. Biosci. Bioeng. 2001, 92, 237-241


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