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Progress Towards the Total Synthesis of Petrosaspongiolide L and Small Molecule Control of Nucleic Acid Function

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 (Unpublished)

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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.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Kilgore, Austinabk76@pitt.eduabk76
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairDeiters, AlexanderDEITERS@pitt.eduDEITERS
Committee MemberChilders, Sethwschild@pitt.eduwschild
Committee MemberFloreancig, Paulflorean@pitt.eduflorean
Date: 8 June 2020
Date Type: Publication
Defense Date: 2 April 2020
Approval Date: 8 June 2020
Submission Date: 8 April 2020
Access Restriction: 2 year -- Restrict access to University of Pittsburgh for a period of 2 years.
Number of Pages: 88
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: N/A
Date Deposited: 08 Jun 2020 15:09
Last Modified: 08 Jun 2022 05:15


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