Fusidane

Fusidane
Names
IUPAC name
29-Norprotostane
Systematic IUPAC name
(1R,3aS,3bS,5aS,6R,9aS,9bS,11aS)-3a,3b,6,9a-Tetramethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Other names
29-nor protostane
Identifiers
3D model (JSmol)
  • InChI=1S/C29H52/c1-20(2)10-8-11-21(3)23-15-18-28(6)25(23)13-14-26-27(5)17-9-12-22(4)24(27)16-19-29(26,28)7/h20-26H,8-19H2,1-7H3/t21-,22-,23-,24+,25+,26+,27+,28+,29+/m1/s1
    Key: NOEMICWEDLSYHV-SNZQGMLHSA-N
  • C[C@@H]1CCC[C@]2([C@H]1CC[C@]3([C@H]2CC[C@@H]4[C@@]3(CC[C@@H]4[C@H](C)CCCC(C)C)C)C)C
Properties
C29H52
Molar mass 400.735 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fusidane or 29-norprotostane is a tetracyclic triterpene and the parent structure of a series of steroids, such as the antibiotics fusidic acid,[1][2] helvolic acid, and cephalosporin P1.[3]

Fusidic acid

See also

References

  1. ^ Zhao M, Gödecke T, Gunn J, Duan JA, Che CT (2013). "Protostane and Fusidane Triterpenes: A Mini-Review". Molecules. 18 (4): 4054–4080. doi:10.3390/molecules18044054. PMC 3901436. PMID 23563857.
  2. ^ Chen MM, Wang FQ, Lin LC, Yao K, Wei DZ (2012). "Characterization and application of fusidane antibiotic biosynethsis enzyme 3-ketosteroid-∆1-dehydrogenase in steroid transformation". Appl Microbiol Biotechnol. 96 (1): 133–142. doi:10.1007/s00253-011-3855-5. PMID 22234537. S2CID 2893266.
  3. ^ Li, Xiangchen; Cheng, Jian; Liu, Xiaonan; Guo, Xiaoxian; Liu, Yuqian; Fan, Wenjing; Lu, Lina; Ma, Yanhe; Liu, Tao; Tao, Shiheng; Jiang, Huifeng (1 October 2020). "Origin and Evolution of Fusidane-Type Antibiotics Biosynthetic Pathway through Multiple Horizontal Gene Transfers". Genome Biology and Evolution. 12 (10): 1830–1840. doi:10.1093/gbe/evaa163. PMC 7750971.

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