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Synthetic studies directed toward investigation of cholesterol regulation.

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Call No.	QP752.C5 R87 1999
Author	Russel, Jonathon S.
Title	Synthetic studies directed toward investigation of cholesterol regulation.
Date	1999
Abstract	Chapter II of this thesis describes the synthesis of a number of sulfobetaines and bissulfobetaines to be evaluated as inhibitors of squalene synthase (SS) on the basis of the idea proposed by Shechter that their zwitterionic structure would be conducive both to binding in the active site and to passage through cell membranes. Since SS catalyzes the reductive dimerization of two molecules of farnesyl diphosphate (FPP) to squalene via the intermediate presqualene diphosphate (PSPP), the basic strategy employed by our and other laboratories for the development of inhibitors of this enzyme has involved the preparation of agents that are intended to mimic the structural and electronic properties of FPP, PSPP, or any of a number of putative carbocationic intermediates that may be formed in the pathway from FPP to squalene. Chapter III of this thesis describes the preparation of a number of oxysterols, sterols containing a second oxygen atom, which have been implicated as regulators of various aspects of cholesterol metabolism and transport. Recent studies have demonstrated that oxysterols serve as ligands for a family of transcription factors known as the LXR receptors. Our laboratory has been working in collaboration with a group at Glaxo Wellcome toward the preparation of both natural and unnatural oxysterols for testing as ligands for the nuclear LXR receptors. Chapter IV of this thesis describes efforts in collaboration with Fielding directed toward the development of a tritiated photoaffinity label for caveolin, a family of proteins that may play an important role in the transport of free cholesterol out of cells. Specific efforts have been directed toward the synthesis of steroid-benzophenone conjugates.
Description	1 online resource (xv, 163 leaves) : illustrations
Format	application/pdf
Advisor	Spencer, Thomas A., Jr.
Subject	Cholesterol -- Synthesis -- Regulation. ; Anticholesteremic agents -- Synthesis. ; Squalene.
College	Dartmouth College -- Department of Chemistry.
Issuing Body	Dartmouth Dissertations are made available through the Dartmouth Digital Library.
Degree	Thesis (Ph.D)--Dartmouth College.
Copyright	In Copyright. This material is protected by copyright and/or related rights. You are free to use this material in any way that is permitted by copyright law that applies to your use. For other uses, you need to obtain permission from the rights-holder(s). http://rightsstatements.org/page/InC/1.0/
DOI	https://doi.org/10.1349/ddlp.3363

Title	russel1999 1
Full Text	Synthetic Studies Directed Toward Investigation of Cholesterol Regulation A Thesis Submitted to the Faculty in partial fulfillment of the requirements for the degree o f Doctor of Philosophy in Chemistry by Jonathon S. Russel Dartmouth College Hanover, New Hampshire March 1999 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.

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