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

被引：10

作者：

Isidro, Albert ^{[1
]}

Latassa, Daniel ^{[2
]}

Giraud, Matthieu ^{[2
]}

Alvarez, Mercedes ^{[1
,3
,4
]}

Albericio, Fernando ^{[1
,3
,5
]}

机构：

[1] Barcelona Sci Pk, Inst Res Biomed, Barcelona 08028, Spain

[2] Lonza AG, TIDES, CH-3930 Visp, Switzerland

[3] Barcelona Sci Pk, Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona 08028, Spain

[4] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

[5] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 12期

关键词：

PHASE PEPTIDE-SYNTHESIS; GUANIDINO FUNCTION; ACID; DERIVATIVES; SULFONATION; MECHANISMS; SCAVENGERS; RESIDUES; INDOLE; EDOTN;

D O I：

10.1039/b904836g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2565 / 2569

页数：5

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