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Some non-anomerically C-C-linked carbohydrate amino acids related to leucine - synthesis and structure determination

Bohumil Steiner ; Julia Micova ; Miroslav Koos ; Vratislav Langer (Institutionen för oorganisk miljökemi) ; Dalma Gyepesova
Carbohydrate Research (0008-6215). Vol. 338 (2003), 13, p. 1349-1357.
[Artikel, refereegranskad vetenskaplig]

(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.

Nyckelord: Sugar amino acids, Hydantoins, Leucine, Bucherer–Bergs reaction, Methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose, X-ray crystallography

Denna post skapades 2006-08-29. Senast ändrad 2013-06-04.
CPL Pubid: 3637


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