Some non-anomerically C-C-linked carbohydrate amino acids related to leucine - synthesis and structure determination
Artikel i vetenskaplig tidskrift, 2003

(5'R)-5'-Isobutyl-5'-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5'-R configuration was confirmed by X-ray crystallography. Corresponding α-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-α-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-β-L-erythrofuranosid-4-C-yl]-D-leucine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5S configuration, formed in a minority, were also isolated and characterised.

Leucine

Bucherer–Bergs reaction

Hydantoins

Sugar amino acids

3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose

X-ray crystallography

Methyl 6-deoxy-6-isopropyl-2

Författare

Bohumil Steiner

Slovak Academy of Sciences

Julia Micova

Slovak Academy of Sciences

Miroslav Koos

Slovak Academy of Sciences

Vratislav Langer

Chalmers, Institutionen för oorganisk miljökemi

Dalma Gyepesova

Slovak Academy of Sciences

Carbohydrate Research

0008-6215 (ISSN)

Vol. 338 13 1349-1357

Ämneskategorier

Kemi

DOI

10.1016/S0008-6215(03)00176-9