PMID: 6413206Oct 17, 1983Paper

Inhibition of metalloendopeptidases by 2-mercaptoacetyl-dipeptides

European Journal of Biochemistry
S Blumberg, Z Tauber

Abstract

A series of 2-mercaptoacetyl-dipeptides, a potential group of metalloendopeptidase inhibitors, has been synthesized by coupling the N-hydroxysuccinimide ester of S-acetyl-2-mercaptoacetic acid with hydrophobic dipeptide methyl ester hydrochlorides, followed by hydrolysis with NaOH in aqueous methanol and acidification with HCl. Thus, the 2-mercaptoacetyl derivatives of L-phenylalanyl-L-leucine, L-leucyl-L-phenylalanine and L-leucyl-D-phenylalanine were prepared. The first two compounds inhibit effectively thermolysin from Bacillus thermoproteolyticus and a metalloendopeptidase isolated from Streptomyces griseus, with Ki values in the micromolar range or below. The third compound inhibits the two enzymes only poorly, showing the stereospecificity of the inhibition process. These inhibitors should provide a useful tool for the study of bacterial and mammalian metalloendopeptidases (or dipeptidyl carboxypeptidases) and for the assessment of their physiological role.

References

Dec 1, 1975·Archives of Biochemistry and Biophysics·T L Graham, R L Whistler
Dec 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·B Holmquist, B L Vallee
Apr 17, 1979·Biochemistry·M A OndettiD W Cushman
Jul 11, 1978·Biochemistry·N Nishino, J C Powers
Dec 1, 1975·Archives of Biochemistry and Biophysics·T KomiyamaH Umezawa
Dec 17, 1974·British Dental Journal·D H Goose
Jul 26, 1968·Biochemical and Biophysical Research Communications·J Feder
Aug 1, 1970·European Journal of Biochemistry·K Morihara, H Tsuzuki
Oct 14, 1972·Journal of Molecular Biology·P M ColmanB W Matthews
Oct 8, 1969·Biochemical and Biophysical Research Communications·S A LattB L Vallee
Nov 8, 1965·Biochemical and Biophysical Research Communications·H MatsubaraT H Jukes
Apr 20, 1967·Biochemical and Biophysical Research Communications·I Schechter, A Berger
Sep 16, 1981·Biochemical and Biophysical Research Communications·J AlmenoffM Orlowski
Nov 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·R MumfordM Zimmerman
Dec 21, 1981·Life Sciences·R L HudginP L Wood
Dec 3, 1981·European Journal of Pharmacology·M AltsteinZ Vogel
May 31, 1982·Biochemical and Biophysical Research Communications·B Malfroy, J C Schwartz
Oct 15, 1981·Biochemical and Biophysical Research Communications·A L MaycockA A Patchett
May 1, 1959·Archives of Biochemistry and Biophysics·G L ELLMAN
Jul 12, 1972·Nature: New Biology·K TitaniH Neurath
Jul 12, 1972·Nature: New Biology·B W MatthewsD Dupourque
Jul 12, 1972·Nature: New Biology·B W MatthewsH Neurath

Related Concepts

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.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

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.

Hereditary Sensory Autonomic Neuropathy

Hereditary Sensory Autonomic Neuropathies are a group of inherited neurodegenerative disorders characterized clinically by loss of sensation and autonomic dysfunction. Here is the latest research on these neuropathies.

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.

Glut1 Deficiency

Glut1 deficiency, an autosomal dominant, genetic metabolic disorder associated with a deficiency of GLUT1, the protein that transports glucose across the blood brain barrier, is characterized by mental and motor developmental delays and infantile seizures. Follow the latest research on Glut1 deficiency with this feed.

Separation Anxiety

Separation anxiety is a type of anxiety disorder that involves excessive distress and anxiety with separation. This may include separation from places or people to which they have a strong emotional connection with. It often affects children more than adults. Here is the latest research on separation anxiety.

KIF1A Associated Neurological Disorder

KIF1A associated neurological disorder (KAND) is a rare neurodegenerative condition caused by mutations in the KIF1A gene. KAND may present with a wide range and severity of symptoms including stiff or weak leg muscles, low muscle tone, a lack of muscle coordination and balance, and intellectual disability. Find the latest research on KAND here.

Regulation of Vocal-Motor Plasticity

Dopaminergic projections to the basal ganglia and nucleus accumbens shape the learning and plasticity of motivated behaviors across species including the regulation of vocal-motor plasticity and performance in songbirds. Discover the latest research on the regulation of vocal-motor plasticity here.