Antipain

Antipain

Names
IUPAC name N^2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-N^5-(diaminomethylidene)-L-ornithyl-N-{(2S)-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl}-L-valinamide
Identifiers
CAS Number	37691-11-5
3D model (Jmol)	Interactive image
ChemSpider	34678
ECHA InfoCard	100.048.738
PubChem	37817
UNII	47V479BE6L
InChI InChI=1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1 Key: SDNYTAYICBFYFH-TUFLPTIASA-N InChI=1/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1 Key: SDNYTAYICBFYFH-TUFLPTIABE
SMILES O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)N[C@H](C(=O)O)Cc1ccccc1)CCC/N=C(\N)N)C(C)C)CCC/N=C(\N)N
Properties
Chemical formula	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 "Peptide aldehyde complexes with wheat serine carboxypeptidase II: implications for the catalytic mechanism and substrate specificity.". J.Mol.Biol. 225 (5): 714–25. 1996. PMID 8636973.
4. PDB ENTRY 2xe4 "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. 2010. doi:10.1074/jbc.M110.156679. PMC 2998157. PMID 20926390.