Pyrrolostatin

Pyrrolostatin is a lipid peroxidation inhibitor with the molecular formula C15H21NO2 which has been isolated from the bacterium Streptomyces chrestomyceticus.[1][2]

Pyrrolostatin
Names
IUPAC name
4-[(2E)-3,7-Dimethylocta-2,6-dienyl]-1H-pyrrole-2-carboxylic acid[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C15H21NO2/c1-11(2)5-4-6-12(3)7-8-13-9-14(15(17)18)16-10-13/h5,7,9-10,16H,4,6,8H2,1-3H3,(H,17,18)/b12-7+
    Key: UEQIBCOZMSTCSW-KPKJPENVSA-N
  • CC(=CCC/C(=C/CC1=CNC(=C1)C(=O)O)/C)C
Properties
C15H21NO2
Molar mass 247.338 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Pyrrolostatin". Pubchem.ncbi.NLM.nih.gov.
  2. Kato, Shinichiro; Shindo, Kazutoshi; Kawai, Hiroyuki; Odagawa, Atsuo; Matsuoka, Michiko; Mochizuki, Junichiro (1993). "Pyrrolostatin, a novel lipid peroxidation inhibitor from Streptomyces chrestomyceticus. Taxonomy, fermentation, isolation, structure elucidation and biological properties". The Journal of Antibiotics. 46 (6): 892–899. doi:10.7164/antibiotics.46.892. PMID 8344870.

Further reading
  • Schmidt, Jens; Adrian, Juliane; Stark, Christian B. W. (22 July 2015). "Short and highly efficient synthesis of lipid peroxidation inhibitor pyrrolostatin and some analogues thereof". Organic & Biomolecular Chemistry. 13 (30): 8173–8176. doi:10.1039/C5OB01066G. ISSN 1477-0539. PMID 26154919.
  • Dunford, Damian G.; Knight, David W. (22 June 2016). "A brief total synthesis of Pyrrolostatin". Tetrahedron Letters. 57 (25): 2746–2748. doi:10.1016/j.tetlet.2016.05.010. ISSN 0040-4039.
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