PMID: 7082637Mar 30, 1982Paper

A thioamide substrate of carboxypeptidase A

P A BartlettN E Jacobsen


Carbobenzoxythioglycyl-L-phenylalanine [CbzNHCH2C(==S)Phe, Z-Glys-Phe] was synthesized as thioamide analogue of Z-Gly-Phe, a known substrate of carboxypeptidase A (CPA). By use of a ninhydrin-based assay and Z-Gly-Gly-Phe as the substrate, Z-Glys-Phe was shown to be a weak competitive inhibitor of CPA (Ki = 1.4 mM). The L isomer (but not the D) of Z-Glys-Phe proved to be a substrate for CPA (Km = 1.1 mM and kcat = 5.3 s-1 at pH 7.5), binding with comparable affinity to, but hydrolyzing at 10% the rate of, the oxo analogue Z-Gly-Phe. The CPA-catalyzed hydrolysis of Z-Glys-Phe was shown to involve only C-N bond cleavage, to give carbobenzoxythioglycine and phenylalanine.


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Apr 1, 1977·Proceedings of the National Academy of Sciences of the United States of America·R Breslow, D L Wernick
Apr 17, 1979·Biochemistry·M A OndettiD W Cushman
Jun 1, 1974·The Biochemical Journal·R Eisenthal, A Cornish-Bowden
Jan 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·D C Rees, W N Lipscomb
Jun 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·D C ReesW N Lipscomb
Jul 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·W N Lipscomb
Sep 16, 1981·Biochemical and Biophysical Research Communications·W L MockJ W Tsang


Oct 1, 1986·Journal of Inorganic Biochemistry·M D BondB L Vallee
Sep 27, 2000·Biochimica Et Biophysica Acta·A Stöckel-MaschekK Neubert
Jan 1, 1999·Bioorganic & Medicinal Chemistry Letters·S YaoJ Chmielewski
Jun 1, 2013·Journal of the American Chemical Society·Kyle L Dunbar, Douglas A Mitchell
Sep 26, 2006·Applied and Environmental Microbiology·Anthony G DodgeLawrence P Wackett
Aug 18, 2005·Organic & Biomolecular Chemistry·Uli Kazmaier, Stefanie Ackermann
Oct 12, 2010·Organic & Biomolecular Chemistry·Uli Kazmaier, Andrea Persch
Apr 1, 1994·European Journal of Biochemistry·M SchutkowskiG Fischer
Jan 30, 2014·Journal of the American Chemical Society·Jacob M GoldbergE James Petersson
Jun 15, 1987·Biochemical and Biophysical Research Communications·V N BalajiS W Dietrich
Jun 19, 2008·FEMS Microbiology Letters·Julia Nowak-JaryJohn W Payne
Mar 9, 2012·The Journal of Organic Chemistry·T M VishwanathaVommina V Sureshbabu
Nov 8, 2018·Angewandte Chemie·Jinhua YangJunfeng Zhao
Mar 24, 2020·Journal of Peptide Science : an Official Publication of the European Peptide Society·Bhavesh KhatriJayanta Chatterjee
Jul 17, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·T T TranJ Perich
May 8, 2018·Chemical Science·Hitesh VermaJayanta Chatterjee
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Oct 1, 1987·International Journal of Peptide and Protein Research·T F La Cour
Oct 1, 1983·International Journal of Peptide and Protein Research·T F La CourS O Lawesson
Oct 1, 1994·International Journal of Peptide and Protein Research·D F MierkeH Kessler
Oct 1, 1984·International Journal of Peptide and Protein Research·G LajoieB Belleau

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