Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/26489
Title: Modification of N-Terminal alpha-Amino groups of peptides and proteins using ketenes
Authors: Chan, AOY
Ho, CM
Chong, HC
Leung, YC 
Huang, JS
Wong, MK 
Che, CM
Issue Date: 2012
Publisher: Amer Chemical Soc
Source: Journal of the American chemical society, 2012, v. 134, no. 5, p. 2589-2598 How to cite?
Journal: Journal of the American Chemical Society 
Abstract: A method of highly selective N-terminal modification of proteins as well as peptides by an isolated ketene was developed. Modification of a library of unprotected peptides XSKFR (X varies over 20 natural amino acids) by an alkyne-functionalized ketene (1) at room temperature at pH 6.3 resulted in excellent N-terminal selectivity (modified alpha-amino group/modified epsilon-amino group = >99:1) for 13 out of the 20 peptides and moderate-to-high N-terminal selectivity (4:1 to 48:1) for 6 of the 7 remaining peptides. Using an alkyne-functionalized N-hydroxysuccinimide (NHS) ester (2) instead of 1, the modification of peptides XSKFR gave internal lysine-modified peptides for 5 out of the 20 peptides and moderate-to-low N-terminal selectivity (5:1 to 1:4) for 13 out of the 20 peptides. Proteins including insulin, lysozyme, RNaseA, and a therapeutic protein BCArg were selectively N-terminally modified at room temperature using ketene 1, in contrast to the formation of significant or major amounts of di-, tri-, or tetra-modified proteins in the modification by NHS ester 2. The 1-modified proteins were further functionalized by a dansyl azide compound through click chemistry without the need for prior treatment.
URI: http://hdl.handle.net/10397/26489
ISSN: 0002-7863
DOI: 10.1021/ja208009r
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