Synthesis and structure determination of some sugar amino acids related to alanine and 6-deoxymannojirimycin.
(5'R)-5'-Methyl-5'-[methyl (4S)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 6-deoxy-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-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4S)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-D-alanine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Total deprotection afforded 5-C-carboxy-6-deoxymannojirimycin. Analogously, methyl (5S)-5-amino-5-C-carboxy-5,6-dideoxy-alpha-L-lyxo-hexofuranoside and 5-C-carboxy-6-deoxy-L-mannojirimycin were prepared from the corresponding (5'S)-5'-methyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-D-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione starting from methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-lyxo-hexofuranosid-5-ulose.
Koós
M
M
Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84238, Bratislava, Slovak Republic. chemmiro@savba.sk
Steiner
B
B
Micová
J
J
Langer
V
V
Durík
M
M
Gyepesová
D
D
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012210:Rhamnose / Q000031:analogs & derivatives / Q000737:chemistry*
C435774:6-deoxymannojirimycin; D000606:Amino Sugars; D007202:Indicators and Reagents; D017485:1-Deoxynojirimycin; D000409:Alanine; D012210:Rhamnose