Solid phase and solution synthesis of NvocLys(CO(CH sub(2)) sub(5)NH&#x 2013; NBD)OCH sub(2)CN, a trifunctional fluorescent lysine derivative

Herein, we describe a general strategy for the facile synthesis of a multifunctional amino acid derivative bearing both fluorescent and photolabile groups such as the lysine derivative NvocLys(CO(CH sub(2)) sub(5)NH-NBD)OCH sub(2)CN (1) that can be used as a biophysical tool for studying protein str...

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Bibliographic Details
Published in:Amino acids 2009-02, Vol.36 (2), p.203-207
Main Authors: Patkar, Kshitij A, Highsmith, WEdward, Aldrich, Jane V
Format: Article
Language:English
Subjects:
Amino acids
Carboxylic acids
Derivatives
Lysine
Purification
Strategy
Synthesis
Online Access:Get full text
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Summary:Herein, we describe a general strategy for the facile synthesis of a multifunctional amino acid derivative bearing both fluorescent and photolabile groups such as the lysine derivative NvocLys(CO(CH sub(2)) sub(5)NH-NBD)OCH sub(2)CN (1) that can be used as a biophysical tool for studying protein structure. The synthetic strategy involves functionalization of the amine groups while the amino acid is attached to a solid support, followed by esterification of the carboxylic acid in solution. The solid support protects the caboxylic acid, preventing a side reaction associated with the synthesis in solution and obviating the need for chromatographic purification of several intermediates. This synthetic strategy can be used for the preparation of a variety of amino acid derivatives with unusual alpha -amine and side chain functionalities.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-008-0048-3