Shan Tang, Jing Cheng, Ji‐Shen Zheng
Jul 29, 2015
Citations
0
Influential Citations
5
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A new method compatible with 9-fluorenylmethoxycarbonyl (Fmoc) solid phase peptide synthesis (SPPS) was developed to synthesize photocaged peptides carrying the photosensitive 4-methoxy-7-nitroindoline (MNI) group on the side chain of aspartic acid (Asp) and glutamic acid (Glu). The caged building blocks, Fmoc-Asp(MNI)-OH and Fmoc-Glu(MNI)-OH, could be readily synthesized on multi-gram scale. An important advantage of the new method is that the MNI group prevents the formation of aminosuccinyl side products and pyrrolidones during Fmoc SPPS and has rapid photolysis kinetics. Thus our method provides a useful approach for photocaging of peptides and proteins at side chain carboxylic groups.