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Statine

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This article is about the amino acid. For the group of cholesterol lowering drugs, see Statin.
Statine
Names
IUPAC name (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations AHMHA, Sta
ChEBI
ChemSpider
ECHA InfoCard 100.161.428 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H17NO3/c1-5(2)3-6(9)7(10)4-8(11)12/h5-7,10H,3-4,9H2,1-2H3,(H,11,12)/t6-,7-/m0/s1Key: DFVFTMTWCUHJBL-BQBZGAKWSA-N
SMILES
  • N(CC(C)C)(O)CC(O)=O
Properties
Chemical formula C8H17NO3
Molar mass 175.228 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Statine is a gamma amino acid that occurs twice in the sequence of pepstatin, a protease inhibitor that is active against pepsin and other acid proteases. It is thought to be responsible for the inhibitory activity of pepstatin because it mimics the tetrahedral transition state of peptide catalysis.

References

  1. Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, M.; Takeuchi, T. (1970). "Pepstatin, a new pepsin inhibitor produced by Actinomycetes". The Journal of Antibiotics. 23 (5): 259–262. doi:10.7164/antibiotics.23.259. PMID 4912600.
  2. Marciniszyn Jr, J.; Hartsuck, J. A.; Tang, J. (1976). "Mode of inhibition of acid proteases by pepstatin". The Journal of Biological Chemistry. 251 (22): 7088–7094. doi:10.1016/S0021-9258(17)32945-9. PMID 993206.


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