Structure and Biosynthesis of the Diterpene Hydrocarbon, Casbene
type: CreativeWork
description: The stereochemical course of the enzyme catalyzed cyclization of geranylgeranyl pyrophosphate (GGOPP) to casbene, (1S,14R)-(E,E,E)-3,7,11,15,15-pentamethylbicyclo{14.1.0}pentadeca-2,6,10-triene, was defined in the castor bean plant (Ricinus communis L.,) by resolving the four stereochemical ambiguities in the cyclization. The stereochemical course of the cyclization is defined as follows: (1) the re face of the C-14 carbon of GGOPP is attacked by the C-1 carbon, (2) the E geometry of the double bonds of GGOPP is retained in casbene, (3) the pro-S hydrogen is removed from the C-1 carbon of GGOPP, and (4) the configuration of the 14,15-double bond of GGOPP is retained in the cyclopropane ring of casbene.
abstract: The stereochemical course of the enzyme catalyzed cyclization of geranylgeranyl pyrophosphate (GGOPP) to casbene, (1S,14R)-(E,E,E)-3,7,11,15,15-pentamethylbicyclo{14.1.0}pentadeca-2,6,10-triene, was defined in the castor bean plant (Ricinus communis L.,) by resolving the four stereochemical ambiguities in the cyclization. The stereochemical course of the cyclization is defined as follows: (1) the re face of the C-14 carbon of GGOPP is attacked by the C-1 carbon, (2) the E geometry of the double bonds of GGOPP is retained in casbene, (3) the pro-S hydrogen is removed from the C-1 carbon of GGOPP, and (4) the configuration of the 14,15-double bond of GGOPP is retained in the cyclopropane ring of casbene.
author: Guilford, William Joseph
keywords: Chemistry, Organic
date published: 10000-01-01
date modified: 2026-07-22T22:26:02Z
provider: University of Illinois - Urbana-Champaign
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: University of Illinois at Urbana-Champaign

PropertyValue
property ID: Handle
value: http://hdl.handle.net/2142/70182