Elisabethatriene

Elisabethatriene
Names
Preferred IUPAC name
(1R,4S,4aR)-4-Methyl-1-[(2S)-6-methylhept-5-en-2-yl]-7-methylidene-1,2,3,4,4a,5,6,7-octahydronapthalene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H32/c1-14(2)7-6-8-16(4)19-12-10-17(5)18-11-9-15(3)13-20(18)19/h7,13,16-19H,3,6,8-12H2,1-2,4-5H3/t16-,17-,18+,19+/m0/s1
    Key: DTMNMDQQDKQKIE-INDMIFKZSA-N
  • CC1CCC(C2=CC(=C)CCC12)C(C)CCC=C(C)C
Properties
C20H32
Molar mass 272.476 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Elisabethatriene is a bicyclic compound found in the marine octocoral Pseudopterogorgia elisabethae. It is proposed to act as an intermediate in the synthesis of pseudopterosin or dehydrogenates into erogorgiaene. It is the product of catalysis of geranylgeranyl diphosphate using the Elisabethatriene synthase enzyme. Its stereochemistry is identical to the stereochemistry of elisabethatrienol.

References

  1. 1 2 Nasuda M, Ohmori M, Ohyama K, Fujimoto Y (1 May 2012). "Revision of the stereochemistry of elisabethatriene, a putative biosynthetic intermediate of pseudopterosins". Chemical & Pharmaceutical Bulletin. 60 (5). The Pharmaceutical Society of Japan: 681–685. doi:10.1248/cpb.60.681. PMID 22689408. Archived from the original on 15 January 2017. Retrieved 15 January 2017.
  2. ↑ Kohl AC, Kerr RG (2003-11-26). "Pseudopterosin Biosynthesis: Aromatization of the Diterpene Cyclase Product, Elisabethatriene". Marine Drugs. 1 (1): 54–65. doi:10.3390/md101054. ISSN 1660-3397. PMC 3783875.
  3. ↑ Brück TB, Kerr RG (March 2006). "Purification and kinetic properties of elisabethatriene synthase from the coral Pseudopterogorgia elisabethae". Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology. 143 (3): 269–278. doi:10.1016/j.cbpb.2005.11.016. PMID 16423548.