Elisabethatriene

Last updated
Elisabethatriene
Elisabethatriene.svg
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
PubChem CID
  • 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 . [1] It is proposed to act as a intermediate in the synthesis of pseudopterosin or dehydrogenates into erogorgiaene. [2] It is the product of catalysis of geranylgeranyl diphosphate using the Elisabethatriene synthase enzyme. [3] Its stereochemistry is identical to the stereochemistry of elisabethatrienol. [1]

References

  1. 1 2 Masayuki Nasuda; Miho Ohmori; Kiyoshi Ohyama; Yoshinori Fujimoto (1 May 2012). "Revision of the stereochemistry of elisabethatriene, a putative biosynthetic intermediate of pseudopterosins". Chemical and 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, Amber C.; Kerr, Russell G. (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.
  3. ↑ Brück, Thomas B.; Kerr, Russell G. (2006-03-01). "Purification and kinetic properties of elisabethatriene synthase from the coral Pseudopterogorgia elisabethae". Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology. 143 (3): 269–278. doi:10.1016/j.cbpb.2005.11.016. ISSN   1096-4959.


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