Antipain

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Antipain
Antipain.svg
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
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: SDNYTAYICBFYFH-TUFLPTIASA-N Yes check.svgY
  • 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
  • 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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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]

References

  1. ↑ Suda H, Aoyagi T, Hamada M, Takeuchi T, Umezawa H (April 1972). "Antipain, a new protease inhibitor isolated from actinomycetes". The Journal of Antibiotics. 25 (4): 263–266. doi: 10.7164/antibiotics.25.263 . PMID   4559651.
  2. ↑ Umezawa S, Tatsuta K, Fujimoto K, Tsuchiya T, Umezawa H (April 1972). "Structure of antipain, a new Sakaguchi-positive product of streptomyces". The Journal of Antibiotics. 25 (4): 267–270. doi: 10.7164/antibiotics.25.267 . PMID   5052959.
  3. ↑ Lackie J (2012). A Dictionary of Biomedicine. Oxford University Press. ISBN   9780199549351.
  4. ↑ PDB ENTRY 1bcr Bullock TL, Breddam K, Remington SJ (February 1996). "Peptide aldehyde complexes with wheat serine carboxypeptidase II: implications for the catalytic mechanism and substrate specificity". Journal of Molecular Biology. 255 (5): 714–725. doi:10.1006/jmbi.1996.0058. PMID   8636973.
  5. ↑ PDB ENTRY 2xe4 McLuskey K, Paterson NG, Bland ND, Isaacs NW, Mottram JC (December 2010). "Crystal structure of Leishmania major oligopeptidase B gives insight into the enzymatic properties of a trypanosomatid virulence factor". The Journal of Biological Chemistry. 285 (50): 39249–39259. doi: 10.1074/jbc.M110.156679 . PMC   2998157 . PMID   20926390.
  6. 1 2 3 Akhtarshenas, Bahareh; Karami Shabankareh, Hamed; Hajarian, Hadi; Bucak, Mustafa Numan; Abdolmohammadi, Ali Reza; Dashtizad, Mojtaba (2018). "The protease inhibitor antipain has a beneficial synergistic effect with trehalose for ram semen cryopreservation". Reproduction in Domestic Animals. 53 (6): 1359–1366. doi:10.1111/rda.13253. PMID   30011087. S2CID   51629940.
  7. ↑ Nakae K, Kojima F, Sawa R, Kubota Y, Igarashi M, Kinoshita N, et al. (January 2010). "Antipain Y, a new antipain analog that inhibits neurotransmitter release from rat dorsal root ganglion neurons". The Journal of Antibiotics. 63 (1): 41–44. doi: 10.1038/ja.2009.109 . PMID   19911027.
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