1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
| Autor: | Daniel Latassa, Mercedes Álvarez, Albert Isidro, Fernando Albericio, Matthieu Giraud |
|---|---|
| Přispěvatelé: | Universitat de Barcelona |
| Rok vydání: | 2009 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Indoles Solid-phase synthesis Arginine Chemistry Stereochemistry Organic Chemistry Free Radical Scavengers Hydrogen-Ion Concentration Síntesi de pèptids Sulfinic Acids Radicals lliures (Química) Biochemistry Síntesi en fase sólida Peptide synthesis Peptide chemistry Side chain Free radicals (Chemistry) Physical and Theoretical Chemistry Protecting group Peptides Benzofurans |
| Zdroj: | Dipòsit Digital de la UB Universidad de Barcelona Recercat. Dipósit de la Recerca de Catalunya instname |
| ISSN: | 1477-0539 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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