Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents.
The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.
Carrillo
Nancy
N
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
Davalos
Eric A
EA
Russak
Justin A
JA
Bode
Jeffrey W
JW
D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis*; D014867:Water / Q000737:chemistry
D007555:Isoxazoles; D007651:Keto Acids; D009842:Oligopeptides; D014867:Water