1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine?

Organic & Biomolecular Chemistry Pub Date: 2009-04-23 DOI: 10.1039/B904836G

Abstract

The protection of arginine (Arg) side chains is a crucial issue in peptide chemistry because of the propensity of the basic guanidinium group to produce side reactions. Currently, sulfonyl-type protecting groups, such as 2,2,5,7,8-pentamethylchroman (Pmc) and 2,2,4,6,7-pentamethyldihydrobenzofurane (Pbf), are the most widely used for this purpose. Nevertheless, Arg side chain protection remains problematic as a result of the acid stability of these two compounds. This issue is even more relevant in Arg-rich sequences, acid-sensitive peptides and large-scale syntheses. The 1,2-dimethylindole-3-sulfonyl (MIS) group is more acid-labile than Pmc and Pbf and can therefore be a better option for Arg side chain protection. In addition, MIS is compatible with tryptophan-containing peptides.

Graphical abstract: 1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
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