Antipain

Antipain is an oligopeptide that is isolated from actinomycetes and used in biochemical research as a protease inhibitor of trypsin and papain.^[1] It was discovered in 1972 and was the first natural peptide found that contained an ureylene group.^[2] Antipain can aid in prevention of coagulation in blood. It is an inhibitor of serine and cysteine proteases.^[3]

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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 N
3D model (JSmol)	Interactive image
ChemSpider	34678 Y
ECHA InfoCard	100.048.738
PubChem CID	37817
UNII	47V479BE6L N
CompTox Dashboard (EPA)	DTXSID40958733
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	604.713 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

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It has been crystallized in complexes with carboxypeptidase, which is obtained from wheat,^[4] and Leishmania major oligopeptidase B.^[5] In both cases, the backbone carbonyl of the terminal arginine of antipain forms a covalent bond to the active site serine in the protease.

A study was performed for information on the effect of antipain on the quality of post-thawed ram semen.^[6] The results from this experiment concluded that antipain aided in the quality of ram semen by maintaining the sperm mobility.^[6] Antipain includes the function to inhibit a degrading enzyme, called plasmin, permitting this substance to be able to improve the resistance of membrane disruption by freezing temperatures.^[6]

Antipain Y, a similar chemical compound that is an analog of antipain, which was isolated from a species of Streptomyces, inhibits the release of neurotransmitters in rat dorsal root ganglion neurons.^[7]