L-赤蘚糖, 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°

COA:

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

Reference:

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