Preparation of N- (4'- pyridylmethyl) -4-aminomethyl-3-nitro-benzamide and its application for peptide synthesis solution method

摘要

In this paper, a new compound-N-(4'-pyridylmethyl)-4-aminomethyl-3-nitro- benzamide (HB) which could be used in liquid phase peptide synthesis as a protective group and a amino handle was designed and prepared successfully and its application in liquid phase peptide synthesis were also described. Using p-toluic acid as the starting material, the target amino handle was prepared by a six-steps synthetic procedure. With this handle, a series of protected peptides were synthesized in high yields with DCC-HOBt or TBTU as the coupling reagents. The handle (HB) could not only protect C-terminal groups temporarily, but also make the separation and purification of the synthesized peptides easier and more convenient. The handle (HB) was removed from synthesized protected peptides by photolysis with UV light ( > 320 nm) in methanol/water solution under nitrogen atmosphere(general procedure) and protected peptides amide was easily obtained.