Antipain

Antipain
Names
IUPAC name
N2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-N5-(diaminomethylidene)-L-ornithyl-N-{(2S)-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl}-L-valinamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.738
UNII
Properties
C27H44N10O6
Molar mass 604.71 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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Infobox references

Antipain is an oligopeptide isolated from actinomycetes and used in biochemical research as a protease inhibitor, reported in 1972 as the first natural peptide containing a ureylene group.[1] Specifically, it is an inhibitor of trypsin and papain.[2]

It has been crystallised in complex with carboxypeptidase from wheat[3] and Leishmania major oligopeptidase B.[4] In both cases the backbone carbonyl of the terminal arginine of antipain forms a covalent bond to the active site serine in the protease.

References

  1. Umezawa, S; Tatsuta, K; Fujimoto, K; Tsuchiya, T; Umezawa, H (1972). "Structure of antipain, a new Sakaguchi-positive product of streptomyces". The Journal of Antibiotics. 25 (4): 267–70. doi:10.7164/antibiotics.25.267. PMID 5052959.
  2. Suda, H; Aoyagi, T; Hamada, M; Takeuchi, T; Umezawa, H (1972). "Antipain, a new protease inhibitor isolated from actinomycetes". The Journal of Antibiotics. 25 (4): 263–6. doi:10.7164/antibiotics.25.263. PMID 4559651.
  3. PDB ENTRY 1bcr Bullock, TL; Breddam, K; Remington, SJ (1996). "Peptide aldehyde complexes with wheat serine carboxypeptidase II: implications for the catalytic mechanism and substrate specificity". J. Mol. Biol. 255 (5): 714–25. doi:10.1006/jmbi.1996.0058. PMID 8636973.
  4. PDB ENTRY 2xe4 McLuskey, K; Paterson, NG; Bland, ND; Isaacs, NW; Mottram, JC (2010). "Crystal Structure of Leishmania Major Oligopeptidase B Gives Insight Into the Enzymatic Properties of a Trypanosomatid Virulence Factor". J. Biol. Chem. 285 (50): 39249–59. doi:10.1074/jbc.M110.156679. PMC 2998157. PMID 20926390.
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