Synthesis of New Trisulfonated Calix[4]arenes Functionalized at the Upper Rim, and Their Complexation with the Trimethyllysine Epigenetic Mark

被引：54

作者：

Daze, Kevin D. ^{[1
]}

Ma, Manuel C. F. ^{[1
]}

Pineux, Florent ^{[1
]}

Hof, Fraser ^{[1
]}

机构：

[1] Univ Victoria, Dept Chem, STN CSC, Victoria, BC, Canada

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 06期

关键词：

AMINO-ACIDS; BINDING; WATER; ARGININE; LYSINE;

D O I：

10.1021/ol300243b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic route to produce a new family of trisulfonated calix[4]arenes bearing a single group, selectively introduced, that lines the binding pocket is reported. Ten examples, including new sulfonamide and biphenyl-substituted hosts, each with additional binding elements, demonstrate the tuning of guest affinities and selectivities. NMR titrations in phosphate-buffered water show that one of the new hosts binds to the modified amino acid trimethyllysine with the highest affinity and selectivity observed to date.

引用

页码：1512 / 1515

页数：4

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