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Title: 1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
Author: Isidro Llobet, Albert
Latassa, Daniel
Giraud, Matthieu
Álvarez Domingo, Mercedes
Albericio Palomera, Fernando
Keywords: Síntesi de pèptids
Radicals lliures (Química)
Síntesi en fase sólida
Peptide synthesis
Free radicals (Chemistry)
Solid-phase synthesis
Issue Date: 23-Apr-2009
Publisher: Royal Society of Chemistry
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.
Note: Versió postprint del document publicat a:
It is part of: Organic & Biomolecular Chemistry, 2009, vol. 7, num. 12, p. 2565-2569
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ISSN: 1477-0520
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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