eprintid: 39301
rev_number: 29
userid: 3519
dir: disk0/00/03/93/01
datestamp: 2020-09-16 13:48:53
lastmod: 2020-09-16 13:48:53
status_changed: 2020-09-16 13:48:53
type: thesis_degree
metadata_visibility: show
contact_email: maf174@pitt.edu
eprint_status: archive
creators_name: Frasso, Michael
creators_email: maf174@pitt.edu
creators_id: maf174
title: Synthetic Approaches to Cardiolipin Analogs
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: cardiolipin, organic synthesis
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.
date: 2020-09-16
date_type: published
pages: 145
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Wipf, Peter
etdcommittee_name: Kagan, Valerian
etdcommittee_name: Horne, Seth
etdcommittee_name: Koide, Kazunori
etdcommittee_email: pwipf@pitt.edu
etdcommittee_email: kagan@pitt.edu
etdcommittee_email: horne@pitt.edu
etdcommittee_email: koide@pitt.edu
etd_defense_date: 2020-06-19
etd_approval_date: 2020-09-16
etd_submission_date: 2020-07-01
etd_release_date: 2020-09-16
etd_access_restriction: immediate
etd_patent_pending: FALSE
thesis_type: dissertation
degree: PhD
citation:   Frasso, Michael  (2020) Synthetic Approaches to Cardiolipin Analogs.  Doctoral Dissertation, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/39301/26/Frasso%20Final%20ETD.pdf