Reduction of methionine sulfoxide with NH4I/TFA:: Compatibility with peptides containing cysteine and aromatic amino acids

被引：25

作者：

Vilaseca, M ^{[1
]}

Nicolás, E ^{[1
]}

Capdevila, F ^{[1
]}

Giralt, E ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1998年 / 54卷 / 50期

关键词：

solid-phase synthesis; peptides; protecting groups; sulfoxides;

D O I：

10.1016/S0040-4020(98)00954-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of methionine sulfoxide with ammonium iodide in trifluoroacetic acid has been studied in peptides containing cysteine, histidine, tyrosine or tryptophan residues. While histidine and tyrosine have proved to be stable under the experimental conditions, cysteine is oxidized to cystine and tryptophan dimerizes to form 2-indolylindolenine derivatives. The use of methyl sulfide to increase the reduction rate minimizes the problem and protection of indole ring with the formyl group avoids the side reaction for this amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：15273 / 15286

页数：14

共 6 条

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