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Squalene cyclization

Citation

Schaefer, Phillip Cuthbert (1969) Squalene cyclization. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-10032002-124237

Abstract

It has been observed that the proton, which is located at C-14 in squalene or C-13 in the "presterol cation," migrates less than 10% of the time (with a confidence level of 74%) to C-20 in lanosterol, and therefore 90% of the time (with a confidence level of 74%) to C-17 in lanosterol. If enzymatically controlled reactions are stereospecific, then at C-13/C17/C-20 in the "presterol cation," there are two sequential 1, 2-migrations during the backbone rearrangement to form lanosterol. A theoretical interpretation of this observation, which reflects on the stereochemistry of the C-18/C-19 double bond of squalene just prior to cyclization, is presented.

A theoretical discussion of the minimal requirements for binding squalene-2, 3-oxide to an enzyme in order to obtain complete stereochemical control over the product is presented.

Item Type:Thesis (Dissertation (Ph.D.))
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Richards, John H.
Thesis Committee:
  • Davidson, Norman R.
  • Bergman, Robert G.
Defense Date:9 September 1968
Record Number:CaltechETD:etd-10032002-124237
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-10032002-124237
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:3881
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:04 Oct 2002
Last Modified:26 Dec 2012 03:03

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