Novel furanoid alpha-substitued alpha-amino acid as a potent turn mimic in peptide synthesis.
A stereoselective approach has been developed to the new sugar amino acid and potential potent turn mimic 5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-alpha-D-xylofuranose 3-C-carboxylic acid (12), via the [3,3]-sigmatropic rearrangement of allylic thiocyanates (Z)-6 and (E)-7, prepared from D-xylose. The synthesis of a new dipeptide 13 is also described.
Martinková
Miroslava
M
Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Safárik University, Moyzesova 11, SK-040 01 Kosice, Slovak Republic. mmartin@kosice.upjs.sk
Gonda
Jozef
J
Raschmanová
Jana
J
D000596:Amino Acids / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D018716:Molecular Mimicry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry*
D000596:Amino Acids; D004151:Dipeptides; D010455:Peptides; D013400:Sugar Acids