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Synthetic Approaches to Cardiolipin Analogs

Frasso, Michael (2020) Synthetic Approaches to Cardiolipin Analogs. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The first portion of this document describes the synthesis of three examples of the mitochondrial phospholipid cardiolipin with different fatty acid chain lengths and degrees of unsaturation. These compounds enabled the assessment of the phospholipase Cld1’s hydrolysis specificity for different fatty acid esters in cardiolipin.
During the final deprotection reaction of the synthesis, trace hydrolysis of the cardiolipin acyl groups occurred. To ameliorate this issue, a new protecting group scheme was devised, along with conditions for the selective cleavage of a primary triethylsilyl ether in the presence of a vicinal, secondary triethylsilyl ether, of which there are a surprisingly limited number of examples.
Finally, a new method for cardiolipin synthesis was developed. The method was inspired by the biosynthetic remodeling of cardiolipin and allows for one of the fatty acids to be incorporated later in the synthetic, making it ideal for precious or sensitive fatty acids.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Frasso, Michaelmaf174@pitt.edumaf174
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.edu
Committee MemberKagan, Valeriankagan@pitt.edu
Committee MemberHorne, Sethhorne@pitt.edu
Committee MemberKoide, Kazunorikoide@pitt.edu
Date: 16 September 2020
Date Type: Publication
Defense Date: 19 June 2020
Approval Date: 16 September 2020
Submission Date: 1 July 2020
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 145
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: cardiolipin, organic synthesis
Date Deposited: 16 Sep 2020 13:48
Last Modified: 16 Sep 2020 13:48
URI: http://d-scholarship.pitt.edu/id/eprint/39301

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