Chemistry Letters, Vol.39, No.3, 196-197, 2010
Selective Coupling at the alpha-Amino Group of Cysteine Using Transfer Active-ester-condensation Technology to Synthesize a Linear Octadecapeptide
The peptide segment Fmoc-Ubiquitin(67-76)-NHNH2 was converted to the active ester Fmoc-Ubiquitin(67-76)-OCt and reacted with an unprotected seven residue fragment (H-mNGF(110-117)-OH) from murine Nerve Growth Factor, which contains a Cys at the N-terminus and a free E-amino group at Lys(115)), using transfer active-ester-condensation (TAEC) technology. The linear product H-Ubiquitin(67-76)-murine Nerve Growth Factor(110-117)-OH was formed exclusively through the native chemical ligation mechanism.