Chemistry:Talopeptin

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Talopeptin
Talopeptin.png
Names
Systematic IUPAC name
(2S)-2-{(2S)-2-[(Hydroxy{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphoryl)amino]-4-methylpentanamido}-3-(1H-indol-3-yl)propanoic acid
Other names
N-(N-{[(6-Deoxy-α-L-talopyranosyl)oxy]hydroxyphosphinyl}-L-leucyl)-L-tryptophan
Identifiers
3D model (JSmol)
ChemSpider
Properties
C23H34N3O10P
Molar mass 543.510 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Talopeptin is a chemical compound derived from cultures of Streptomyces. It is a known reversible inhibitor of thermolysin[1] and is expected to inhibit other metalloproteinases.[2][3] Chemically, talopeptin differs from its closely related peptidase inhibitor phosphoramidon by a single stereocenter.

References

  1. Kitagishi, Keiko; Hiromi, Keitaro (1984). "Inhibitory spectrum of talopeptin (MKI), a specific inhibitor of thermolysin". Agricultural and Biological Chemistry 48 (5): 1287–91. doi:10.1271/bbb1961.48.1287. 
  2. Fukuhara, Kenichi; Murao, Sawao; Nozawa, Tsunenori; Hatano, Masahiro (1982). "Structural elucidation of talopeptin (MK-I), a novel metallo proteinase inhibitor produced by Streptomyces mozunensis MK-23". Tetrahedron Letters 23 (22): 2319–22. doi:10.1016/S0040-4039(00)87331-1. 
  3. Kitagishi, Keiko; Hiromi, Keitaro; Oda, Kohei; Murao, Sawao (1983). "Equilibrium study on the binding between thermolysin and Streptomyces metalloprotease inhibitor, talopeptin (MKI)". Journal of Biochemistry 93 (1): 47–53. doi:10.1093/oxfordjournals.jbchem.a134176. PMID 6341369. 

External links