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
CAS Number	37691-11-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	34678 ;
ECHA InfoCard	100.048.738
PubChem CID	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

↑ 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.
↑ 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.
↑ 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.
↑ 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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[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.

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
CAS Number	37691-11-5^N
3D model (JSmol)	Interactive image
ChemSpider	34678^Y
ECHA InfoCard	100.048.738
PubChem CID	37817
UNII	47V479BE6L^N
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^Y Key: SDNYTAYICBFYFH-TUFLPTIASA-N^Y 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).
N verify (what is ^YN ?)
Infobox references