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2009-04-23

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

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Recurs relacionat

http://dx.doi.org/10.1039/b904836g

Resum

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.

Matèries

Síntesi de pèptids, Radicals lliures (Química), Síntesi en fase sólida

Matèries (anglès)

Peptide synthesis, Free radicals (Chemistry), Solid-phase synthesis

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citació

ISIDRO LLOBET, Albert, et al. 1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine. Organic & Biomolecular Chemistry. 2009. Vol. 7, num. 12, pags. 2565-2569. ISSN 1477-0520. [consulted: 11 of July of 2026]. Available at: https://hdl.handle.net/2445/55265

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