N-Fmoc-protected(alpha-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation.
N-Fmoc-protected(alpha-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-alpha-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(alpha-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu
Yoshioka
Megumi
M
Narindoshvili
Tamari
T
Chung
Alfred
A
Khashab
Niveen M
NM
D008872:Microwaves; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
D010455:Peptides; D014230:Triazoles; C012771:benzotriazole