Copper-catalysed C-N/C-O coupling in water: a facile access to N-coumaryl amino acids and fluorescent tyrosine & lysine labels

被引：12

作者：

Kumari, Santosh ^{[1
]}

Shakoor, S. M. Abdul ^{[1
]}

Bajaj, Kiran ^{[1
]}

Nanjegowda, S. H. ^{[2
]}

Mallu, P. ^{[2
]}

Sakhuja, Rajeev ^{[1
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[2] Univ Mysore, Dept Chem, Sri Jayachamarajendra Coll Engn, Mysore 570006, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 25期

关键词：

Amino acids; Copper; Water; Catalysis; Labelling; ARYL HALIDES; PROTEIN; MICROWAVE; PROBES; CHEMISTRY; PEPTIDES; EMISSION; ALANINE; DESIGN; GABA;

D O I：

10.1016/j.tetlet.2016.05.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient, ligand free and environmentally benign approach towards the construction of sp(2) C-sp(3) N bond has been developed via copper catalysed Ullmann type of coupling between 4-chlorocoumarin with N-terminus unprotected amino acids in microwave-aqua conditions, yielding a series of N-coumaryl amino acids in good to excellent yields. Excellent photo-physical properties exhibited by these N-coumaryl amino acids and their chemical applicability as C-terminus coupling partners for N-terminus peptides make them potential fluorescent probes in labelling studies. The methodology was extended towards the C-O and C-N coupling for the synthesis of fluorescent coumaryl labelled tyrosine and lysine labels respectively. Application of coumaryl labelled tyrosine was further explored towards the synthesis of fluorescent labelled opioid tetrapeptide, Endomorphin-2 derivative. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2732 / 2736

页数：5

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