Some non-anomerically C-C-linked carbohydrate amino acids related to leucine-synthesis and structure determination |
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Authors: | Steiner Bohumil Micová Júlia Koós Miroslav Langer Vratislav Gyepesová Dalma |
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Affiliation: | Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84538, Bratislava, Slovakia. |
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Abstract: | (5'R)-5'-Isobutyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5'-R configuration was confirmed by X-ray crystallography. Corresponding alpha-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-beta-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. |
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Keywords: | Sugar amino acids Hydantoins, Leucine Bucherer-Bergs reaction Methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-α- smallcaps" >d-lyxo-hexofuranosid-5-ulose X-ray crystallography |
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