Radical arylation of tyrosine residues in peptides

被引：13

作者：

Fehler, Stefanie K. ^{[1
]}

Pratsch, Gerald ^{[1
]}

Ostreicher, Christiane ^{[2
]}

Furst, Michael C. D. ^{[1
]}

Pischetsrieder, Monika ^{[2
]}

Heinrich, Markus R. ^{[1
]}

机构：

[1] Friedrich Alexander Univ Erlangen Nurnberg, Pharmazeut Chem, Dept Chem & Pharm, Schuhstr 19, D-91052 Erlangen, Germany

[2] Friedrich Alexander Univ Erlangen Nurnberg, Lebensmittelchem, Dept Chem & Pharm, Schuhstr 19, D-91052 Erlangen, Germany

来源：

TETRAHEDRON | 2016年 / 72卷 / 48期

关键词：

Radical reaction; Arylation; Diazonium; Tyrosine; Peptide; C-H ACTIVATION; HOMOLYTIC AROMATIC-SUBSTITUTION; SUZUKI-MIYAURA REACTION; DIAZONIUM SALTS; CATIONIC PHENYLATION; ANILINES; ARYLHYDRAZINES; NEUROTENSIN; COMPLEXES; PHENYLDIAZENES;

D O I：

10.1016/j.tet.2016.04.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The radical arylation of the phenolic side chain of tyrosine in peptides was investigated. Aryl radicals were generated from aryldiazonium salts using titanium(III) chloride as stoichiometric reductant. Due to the high selectivity with which 3-aryltyrosine derivatives were formed, this reaction type represents a new strategy for the direct functionalization of peptides. (C) 2016 Published by Elsevier Ltd.

引用

页码：7888 / 7893

页数：6

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