Smart Hybrid Materials (SHMs)
Khashab Research Group
Innovatively Functionalized Nanomaterials for Biomedical, Sensing and Composites Applications

Publication-8

N-Fmoc-Protected(α-dipeptidoyl)benzotriazoles for Efficient Solid-Phase Peptide Synthesis by Segment Condensation

Yoshioka, M.; Narindoshvili, T.; Chung, A.; Khashab, N. M.; Katritzky, A. R. N-Fmoc-Protected(α-dipeptidoyl)benzotriazoles for Efficient Solid-Phase Peptide Synthesis by Segment Condensation. Chem. Biol. Drug Des. 2008, 72, 182-188
Yoshioka, M.; Narindoshvili, T.; Chung, A.; Khashab, N. M.; Katritzky, A. R.
Fmoc strategy, microwave irradiation, N-Fmocprotected( a-dipeptidoyl)benzotriazoles, segment condensation, solidphase peptide synthesis
2008
N-Fmoc-protected (α-aminoacyl)benzotriazoles I (R1 = CH2Ph, CH2CH2SMe, indolylmethyl, iso-Bu) readily react with L-amino acids H2NCH(R2)CO2H (R2 = Me, CH2CH2SMe, CH2Ph) to afford chiral N-Fmoc-protected-α-dipeptides II (77-89%). II react with 1H-benzotriazole in presence of thionyl chloride in DCM to afford Fmoc(α-dipeptidoyl)benzotriazoles III (71% av. yield). Under mild microwave irradn., III are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).