Solid phase and solution synthesis of NvocLys(CO(CH2) 5NH-NBD)OCH2CN, a trifunctional fluorescent lysine derivative

Kshitij A. Patkar, W. Edward Highsmith, Jane V. Aldrich

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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 α-amine and side chain functionalities.

Original languageEnglish (US)
Pages (from-to)203-207
Number of pages5
JournalAmino Acids
Volume36
Issue number2
DOIs
StatePublished - Feb 2009

Keywords

  • Fluorescent amino acid
  • Lysine
  • NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl)
  • Nvoc (nitroveratryloxycarbonyl)
  • Photolabile protecting group
  • Solid phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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