Premium
N ‐Fmoc‐Protected( α ‐Dipeptidoyl)Benzotriazoles for Efficient Solid‐Phase Peptide Synthesis by Segment Condensation
Author(s) -
Katritzky Alan R.,
Yoshioka Megumi,
Narindoshvili Tamari,
Chung Alfred,
Khashab Niveen M.
Publication year - 2008
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2008.00689.x
Subject(s) - condensation , chemistry , yield (engineering) , peptide , peptide synthesis , hexa , solid phase synthesis , microwave irradiation , combinatorial chemistry , phase (matter) , stereochemistry , organic chemistry , medicinal chemistry , catalysis , materials science , biochemistry , physics , metallurgy , thermodynamics
N ‐Fmoc‐protected( α ‐aminoacyl)benzotriazoles 1a–d readily afford chiral N ‐Fmoc‐protected‐ α ‐dipeptides 2a–f (77–89%). Compounds 2a–f are further converted into N ‐Fmoc‐protected( α ‐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%).