Selective peptide chain extension at the N-terminus of aspartic and glutamic acids utilizing 1-(N-protected-alpha-aminoacyl)benzotriazoles.
Diverse N-protected di-(3a-d, 3a + a', 5a-d, 5d + d', and 7a-g) and tripeptides (10a-h) were synthesized under mild reaction conditions in good yields (65-97%) by acylation with 1-(N-protected-alpha-aminoacyl)benzotriazoles of the amino groups of free aspartic and glutamic acids. Complete retention of chirality was demonstrated by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of dipeptides and tripeptides, and supported 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
Cusido
Janet
J
Angrish
Parul
P
Shestopalov
Alexander A
AA
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