1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine.
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.
Isidro
Albert
A
Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain.
Latassa
Daniel
D
Giraud
Matthieu
M
Alvarez
Mercedes
M
Albericio
Fernando
F
D001120:Arginine / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013441:Sulfinic Acids / Q000737:chemistry*
C543052:1,2-dimethylindole-3-sulfonyl chloride; D001572:Benzofurans; D016166:Free Radical Scavengers; D007211:Indoles; D010455:Peptides; D013441:Sulfinic Acids; D001120:Arginine