Efficient synthesis of enantiopure beta-amino-gamma-keto acids from l-homoserine.
[reaction: see text] A variety of beta-amino-gamma-keto acids were prepared in four steps from commercially available l-homoserine. The reaction sequence is highlighted by a Ni-catalyzed Grignard addition to a N-protected derivative of l-homoserine. One of the beta-amino-gamma-keto acids was then used to create a beta-peptide trimer composed solely of beta-amino-gamma-keto acids.
Sharma
Anil K
AK
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA.
Hergenrother
Paul J
PJ
D006714:Homoserine / Q000737:chemistry*; D007651:Keto Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis; D013237:Stereoisomerism
D007651:Keto Acids; D009842:Oligopeptides; D006714:Homoserine