TY - JOUR
T1 - Solid phase and solution synthesis of NvocLys(CO(CH2) 5NH-NBD)OCH2CN, a trifunctional fluorescent lysine derivative
AU - Patkar, Kshitij A.
AU - Highsmith, W. Edward
AU - Aldrich, Jane V.
N1 - Funding Information:
This project was supported in part by a grant from the National Cancer Institute R21 CA 77033. The authors would like to thank Dr. Santosh Kulkarni for his help with the NMR spectroscopy.
PY - 2009/2
Y1 - 2009/2
N2 - 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.
AB - 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.
KW - Fluorescent amino acid
KW - Lysine
KW - NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl)
KW - Nvoc (nitroveratryloxycarbonyl)
KW - Photolabile protecting group
KW - Solid phase synthesis
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U2 - 10.1007/s00726-008-0048-3
DO - 10.1007/s00726-008-0048-3
M3 - Article
C2 - 18365133
AN - SCOPUS:59449108971
SN - 0939-4451
VL - 36
SP - 203
EP - 207
JO - Amino Acids
JF - Amino Acids
IS - 2
ER -