Synthesis and structure determination of some nonanomerically C—C-linked serine glycoconjugates structurally related to mannojirimycin
Journal article, 2004

The Bucherer–Bergs reaction of methyl 2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose gave (4′S)-4′-carbamoyl-4′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-oxazolidin-2′-one instead of expected hydantoins. A mixture of hydantoins––(5′R)-triphenylmethoxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione and (5′S)-triphenylmethoxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione was obtained from the 5-ulose having protected primary OH group at C-6. The 4′-S configuration of 2 as well as 5′-S configuration of (5′S)-hydroxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione (9) was confirmed by X-ray crystallography. Corresponding α-amino acid––methyl (5S)-5-amino-5-C-carboxy-5-deoxy-α-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-β-L-erythrofuranosid-4-C-yl]-L-serine) (11) was obtained from the hydantoin 9 by acid hydrolysis of the isopropylidene and trityl groups followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5-R configuration, formed in a minority, were also isolated and characterised.

X-ray crystallography

Serine

Sugar amino acids

Mannojirimycin

Hydantoins

Conformation

Bucherer–Bergs reaction

Author

Julia Micova

Slovak Academy of Sciences

Bohumil Steiner

Slovak Academy of Sciences

Miroslav Koos

Slovak Academy of Sciences

Vratislav Langer

Chalmers, Department of Environmental Inorganic Chemistry

Dalma Gyepesova

Slovak Academy of Sciences

Carbohydrate Research

0008-6215 (ISSN)

Vol. 339 13 2187-2195

Subject Categories

Chemical Sciences

DOI

10.1016/j.carres.2004.06.020

More information

Created

10/7/2017