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A tris (2-carboxyethyl) phosphine (TCEP) related cleavage on cysteine-containing proteins. 2010
Peiran Liu, and
Brian W O'Mara, and
Bethanne M Warrack, and
Wei Wu, and
Yunping Huang, and
Yihong Zhang, and
Rulin Zhao, and
Mei Lin, and
Michael S Ackerman, and
Peter K Hocknell, and
Guodong Chen, and
Li Tao, and
Siegfried Rieble, and
Jack Wang, and
David B Wang-Iverson, and
Adrienne A Tymiak, and
Michael J Grace, and
Reb J Russell
Department of Biologics Product and Process Development, Bristol-Myers Squibb Technical Operations, Princeton, New Jersey 08543, USA.
Introduced in the late 1980s as a reducing reagent, Tris (2-carboxyethyl) phosphine (TCEP) has now become one of the most widely used protein reductants. To date, only a few studies on its side reactions have been published. We report the observation of a side reaction that cleaves protein backbones under mild conditions by fracturing the cysteine residues, thus generating heterogeneous peptides containing different moieties from the fractured cysteine. The peptide products were analyzed by high performance liquid chromatography and tandem mass spectrometry (LC/MS/MS). Peptides with a primary amine and a carboxylic acid as termini were observed, and others were found to contain amidated or formamidated carboxy termini, or formylated or glyoxylic amino termini. Formamidation of the carboxy terminus and the formation of glyoxylic amino terminus were unexpected reactions since both involve breaking of carbon-carbon bonds in cysteine.
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