An Fmoc-compatible method for synthesis of peptides containing photocaged aspartic acid or glutamic acid. Issue 31 (29th July 2015)

• Record Type: Journal Article
• Authors: Tang, Shan; Cheng, Jing-Yuan; Zheng, Ji-Shen
• Is Part Of: Tetrahedron letters. Volume 56:Issue 31(2015)
• Page Start: 4582
• Page End: 4585
• Publication Date: 2015-07-29
• Subjects: Photocaged peptides/proteins -- Carboxylic acid moiety -- 4-Methoxy-7-nitroindoline -- Fmoc SPPS -- Biological studies; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.016
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical 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.