Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides.
N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e'), and (3g+3g'), aminoxy hybrid peptides 4a-h, (4a+4a'), 6a-d, 9a-e, (9a+9a'), and (9b+9b'), and alpha-aminoxy peptides 10a,b in good yields without racemization.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Avan
Ilker
I
Tala
Srinivasa R
SR
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D009842:Oligopeptides