Statine

Last updated
Statine
Statine skeletal.svg
Names
IUPAC name
(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid
Identifiers
3D model (JSmol)
AbbreviationsAHMHA, Sta
ChEBI
ChemSpider
ECHA InfoCard 100.161.428 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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/s1
    Key: DFVFTMTWCUHJBL-BQBZGAKWSA-N
  • N[C@@H](CC(C)C)[C@@H](O)CC(O)=O
Properties
C8H17NO3
Molar mass 175.228 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1] It is thought to be responsible for the inhibitory activity of pepstatin because it mimics the tetrahedral transition state of peptide catalysis. [2]

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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