Synthesis of optically active amino acid derivatives via dynamic kinetic resolution.
The complete conversion of racemic amino acid amides to optically active amino acid derivatives was accomplished via lipase/palladium-catalyzed dynamic kinetic resolution (DKR). In the DKR, a lipase catalyzes the selective acylation of L-substrate in the presence of acyl donor while unreacted D-substrate is isomerized by a Pd nanocatalyst to L-substrate. The DKR reactions provided good yields (80-98%) and high enantiomeric excess (95-98% ee). Interestingly, the DKR reactions of phenylglycine amide in the presence of Z-Gly-OMe or Z-Gly-Gly-OMe yielded optically active di- and tripeptide .
Choi
Yoon Kyung
YK
Department of Chemistry, Pohang University of Science and Technology, San-31 Hyojadong, Pohang 790-784, Korea.
Kim
Yunwoong
Y
Han
Kiwon
K
Park
Jaiwook
J
Kim
Mahn-Joo
MJ
D000215:Acylation; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D055162:Biocatalysis; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D004151:Dipeptides; D009842:Oligopeptides; C470025:phenylglycinamide; D010165:Palladium; D008049:Lipase; D005998:Glycine