eprintid: 38629
rev_number: 26
userid: 9666
dir: disk0/00/03/86/29
datestamp: 2020-06-08 15:09:03
lastmod: 2020-06-08 15:09:03
status_changed: 2020-06-08 15:09:03
type: thesis_degree
metadata_visibility: show
contact_email: austinkilgore959@gmail.com
eprint_status: archive
creators_name: Kilgore, Austin
creators_email: abk76@pitt.edu
creators_id: abk76
title: Progress Towards the Total Synthesis of Petrosaspongiolide L and Small Molecule Control of Nucleic Acid Function
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: restricted
keywords: N/A
abstract: Since their discovery in 1997, the Petrosaspongiolide family of marine natural products has gained interest due to their potency and selectivity as phospholipase A2 inhibitors. Petrosaspongiolide L is unique within this family of compounds due to its pyridine containing tetracyclic ring structure that closely resembles the biologically active Spongidines. This pyridine moiety makes it an ideal candidate to highlight a microwave-mediated [2+2+2] cyclotrimerization reaction. Two different strategies were attempted in the synthesis of a key diyne intermediate.
Conditional control of nucleic acid function has become an important method of elucidating gene function as well as a potential candidate in the treatment of multiple disorders. Endogenously, non-coding RNA utilizes the specificity of Watson-Crick base pairing to regulate gene expression. Expanding on these interactions, researchers have succeeded in manipulating these pathways by exposing cells and organisms to synthetic plasmids and oligonucleotides. Modifications to synthetic nucleic acids (backbone modifications, caging groups, etc.) have increased their stability and specificity while also allowing spatiotemporal control of their function. Surprisingly, small molecule induced bioorthogonal transformations have yet to be applied to the control of modified nucleic acids. The progress towards the design and optimization of synthetic linkers capable of cleaving a nucleic acid backbone via a simple alloc deprotection is discussed herein.
date: 2020-06-08
date_type: published
pages: 88
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Deiters, Alexander
etdcommittee_name: Childers, Seth
etdcommittee_name: Floreancig, Paul
etdcommittee_email: DEITERS@pitt.edu
etdcommittee_email: wschild@pitt.edu
etdcommittee_email: florean@pitt.edu
etdcommittee_id: DEITERS
etdcommittee_id: wschild
etdcommittee_id: florean
etd_defense_date: 2020-04-02
etd_approval_date: 2020-06-08
etd_submission_date: 2020-04-08
etd_release_date: 2020-06-08
etd_access_restriction: 2_year
etd_patent_pending: FALSE
thesis_type: thesis
degree: MS
citation:   Kilgore, Austin  (2020) Progress Towards the Total Synthesis of Petrosaspongiolide L and Small Molecule Control of Nucleic Acid Function.  Master's Thesis, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/38629/7/Kilgore%20Final%20ETD.pdf