Synthesis of Chiral beta 3-aminoxy peptides.
A series of chiral beta(3)-aminoxy acids or amides with various side chains have been synthesized via two different approaches. One is the Arndt-Eistert homologation approach, using chiral alpha-aminoxy acids as starting materials. The other approach, utilizing the enantioselective reduction of beta-keto esters catalyzed by baker's yeast or chiral Ru(II) complexes, produces chiral beta(3)-aminoxy acids with nonproteinaceous side chains. The oligomers of beta(3)-aminoxy acids can be readily prepared using EDCI/HOAt as the coupling reagent.
Yang
Dan
D
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China. yangdan@hku.hk
Zhang
Yu-Hui
YH
Li
Bing
B
Zhang
Dan-Wei
DW
D000577:Amides / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D010455:Peptides