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1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
Isidro Llobet, Albert; Latassa, Daniel; Giraud, Matthieu; Álvarez Domingo, Mercedes; Albericio Palomera, Fernando
Universitat de Barcelona
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.
27-06-2014
Síntesi de pèptids
Radicals lliures (Química)
Síntesi en fase sólida
Peptide synthesis
Free radicals (Chemistry)
Solid-phase synthesis
(c) Isidro Llobet, Albert et al., 2009
Artículo
info:eu-repo/semantics/acceptedVersion
Royal Society of Chemistry
         

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