PMID: 7082637Mar 30, 1982Paper

A thioamide substrate of carboxypeptidase A

Biochemistry
P A BartlettN E Jacobsen

Abstract

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.

References

Dec 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·B Holmquist, B L Vallee
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

Citations

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
Apr 6, 2019·Chembiochem : a European Journal of Chemical Biology·Chunxiao LiuE James Petersson
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

Related Concepts

Carbobenzoxyglycylphenylalanine, (D-Phe)-isomer
Amides
Carboxypeptidase
Dipeptides
Spectrophotometry, Ultraviolet
Substrate Specificity
Thioamides
Carboxypeptidase A5

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Lipidomics & Rhinovirus Infection

Lipidomics can be used to examine the lipid species involved with pathogenic conditions, such as viral associated inflammation. Discovered the latest research on Lipidomics & Rhinovirus Infection.

Spatio-Temporal Regulation of DNA Repair

DNA repair is a complex process regulated by several different classes of enzymes, including ligases, endonucleases, and polymerases. This feed focuses on the spatial and temporal regulation that accompanies DNA damage signaling and repair enzymes and processes.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Torsion Dystonia

Torsion dystonia is a movement disorder characterized by loss of control of voluntary movements appearing as sustained muscle contractions and/or abnormal postures. Here is the latest research.

Archaeal RNA Polymerase

Archaeal RNA polymerases are most similar to eukaryotic RNA polymerase II but require the support of only two archaeal general transcription factors, TBP (TATA-box binding protein) and TFB (archaeal homologue of the eukaryotic general transcription factor TFIIB) to initiate basal transcription. Here is the latest research on archaeal RNA polymerases.

Alzheimer's Disease: MS4A

Variants within the membrane-spanning 4-domains subfamily A (MS4A) gene cluster have recently been implicated in Alzheimer's disease in genome-wide association studies. Here is the latest research on Alzheimer's disease and MS4A.

Central Pontine Myelinolysis

Central Pontine Myelinolysis is a neurologic disorder caused most frequently by rapid correction of hyponatremia and is characterized by demyelination that affects the central portion of the base of the pons. Here is the latest research on this disease.