Issue 12, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Albert Isidro,a   Daniel Latassa,b   Matthieu Giraud,b   Mercedes Álvarez*acd  and  Fernando Albericio*ace  

* Corresponding authors

a Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
E-mail: albericio@irbbarcelona.org, mercedes.alvarez@irbbarcelona.org
Fax: +3493 4037126
Tel: +3493 4037088

b Lonza AG., TIDES, Visp, Switzerland

c CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain

d Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain

e Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1, 08028 Barcelona, Spain

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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Article information

DOI
https://doi.org/10.1039/B904836G
Article type
Paper
Submitted
09 Mar 2009
Accepted
16 Mar 2009
First published
23 Apr 2009

Org. Biomol. Chem., 2009,7, 2565-2569

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

A. Isidro, D. Latassa, M. Giraud, M. Álvarez and F. Albericio, Org. Biomol. Chem., 2009, 7, 2565 DOI: 10.1039/B904836G

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