Selective peptide chain extension at the C-terminus of aspartic and glutamic acids utilizing N-protected (alpha-aminoacyl)benzotriazoles.
Aspartic and glutamic acids were selectively extended at each of the alternative C-terminals under mild conditions to afford diverse natural and unnatural N-protected dipeptides and tripeptides in yields of 73-96%. The reactions between N-protected (alpha-aminoacyl)benzotriazoles and free amino acids or dipeptides proceeded with complete retention of chirality as supported by parallel experiments involving D-Ala, L-Ala, and DL-Ala in the preparation of dipeptides and tripeptides, monitored by NMR and HPLC analyses.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu
Todadze
Ekaterina
E
Shestopalov
Alexander A
AA
Cusido
Janet
J
Angrish
Parul
P
D049148:Aminoacylation; D001224:Aspartic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D018698:Glutamic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D009842:Oligopeptides; D014230:Triazoles; D001224:Aspartic Acid; D018698:Glutamic Acid; C012771:benzotriazole