2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

被引：32

作者：

Gimenez, Diana ^{[1
]}

Dose, Anica ^{[1
]}

Robson, Nicholas L. ^{[1
]}

Sandford, Graham ^{[1
]}

Cobb, Steven L. ^{[1
]}

Coxon, Christopher R. ^{[2
]}

机构：

[1] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England

[2] Liverpool John Moores Univ, Sch Pharm & Biomol Sci, Byrom St Campus, Liverpool L3 3AF, Merseyside, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 19期

基金：

英国工程与自然科学研究理事会;

关键词：

TRIFLUOROETHANOL; MIXTURES; ACID; PENTAFLUOROPYRIDINE; MACROCYCLIZATION; POLYPEPTIDES; SUBSTITUTION; DERIVATIVES; MECHANISM; WATER;

D O I：

10.1039/c7ob00295e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both F-19-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multiple nucleophilic side chains currently presents a challenge to the field. Herein, we demonstrate that employing 2,2,2-trifluoroethanol (TFE) as a solvent in peptide SNAr reactions significantly improves nucleophile-selectivity when compared to N, N'-dimethylformamide (DMF).

引用

页码：4081 / 4085

页数：5

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