Some non-anomerically C-C-linked carbohydrate amino acids related to leucine-synthesis and structure determination.
(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.
Steiner
Bohumil
B
Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84538, Bratislava, Slovakia.
Micová
Júlia
J
Koós
Miroslav
M
Langer
Vratislav
V
Gyepesová
Dalma
D
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D006827:Hydantoins / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C484167:(5'R)-5'-isobutyl-5'-(methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl)-imidazolidin-2',4'-dione; D000606:Amino Sugars; D006827:Hydantoins; D007093:Imidazoles; D009005:Monosaccharides; D007930:Leucine