A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins

被引：11

作者：

Nandurkar, Nitin S. ^{[1
]}

Petersen, Rico ^{[1
]}

Qvortrup, Katrine ^{[1
]}

Komnatnyy, Vitaly V. ^{[1
]}

Taveras, Kennedy M. ^{[1
]}

Le Quement, Sebastian T. ^{[1
]}

Frauenlob, Robin ^{[1
]}

Givskov, Michael ^{[2
]}

Nielsen, Thomas E. ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

[2] Univ Copenhagen, Fac Hlth Sci, Dept Int Hlth Immunol & Microbiol, DK-2200 Copenhagen, Denmark

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 52期

关键词：

Hydroxamic acids; Solid-phase synthesis; Hydroxylamine; HDAC inhibitor; PEGA resin; PICTET-SPENGLER REACTION; SCAFFOLD DIVERSITY; PEPTIDE ISOSTERES; INHIBITORS; LINKAGE; FACILE; ESTERS;

D O I：

10.1016/j.tetlet.2011.10.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies for the synthesis of solid-supported lactams and diketopiperazines, respectively, both relying on the high inter- and intramolecular reactivity of cyclic N-acyliminium ions with electron-rich aromatics and heteroaromatics, ultimately affording hydroxamic acid derivatives in high purities. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7121 / 7124

页数：4

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