Solid phase and solution synthesis of NvocLys(CO(CH2)5NH-NBD)OCH2CN, 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(CH2)5NH-NBD)OCH2CN (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.
Patkar
Kshitij A
KA
Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045, USA.
Highsmith
W Edward
WE
Aldrich
Jane V
JV
D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D005456:Fluorescent Dyes; C539752:Nalpha-nitroveratryloxycarbonylamino-N-epsilon-6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoyllysine cyanomethyl ester; D009327:4-Chloro-7-nitrobenzofurazan; D008239:Lysine