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DEVELOPMENT OF A NEW ENANTIOSELECTIVE REDUCTION OF KETONE AND FLUOROGENIC DETECTION OF HYDROGEN PEROXIDE

Basu, Upamanyu (2018) DEVELOPMENT OF A NEW ENANTIOSELECTIVE REDUCTION OF KETONE AND FLUOROGENIC DETECTION OF HYDROGEN PEROXIDE. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

Aberrant splicing related mutations are related to many diseases including cancers while reactive oxygen species (ROS) imbalance is linked to oxidative cellular damage, ultimately leading to aging and neurodegenerative illness. ROS is also known to protect the cells from foreign pathogens due to their oxidative nature. Herein we have taken two different approaches to study them.
In the first chapter, we discuss an improved synthesis of meayamycins, that are powerful modulators of the spliceosome and are used as tools to study splicing mutations. We examined a new enantioselective reduction of prochiral ketone, en route to the synthesis of meayamycin B. We also described the synthesis of new analogue keto-meayamycin D that probes the potency of meayamycins containing other electrophilic functionalities instead of the epoxide group.
In the second chapter, we discussed the need for new fluorescent turn-on probes for a better understanding of how ROS participates in cellular processes. We describe the syntheses of two new probes for the detection of H2O2 that is based on a Mislow-Evans rearrangement. We further studied the stability and kinetics in detail and how they could be beneficial in complimenting the existing probes. Finally, we examined the effect of serum on the Mislow-Evans rearrangement, which is the underlying principle for the H2O2 detection.


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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Basu, Upamanyuupb1@pitt.eduupb1
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairKoide, Kazunorikoide@pitt.edukoide
Committee MemberCurran, Dennis P.curran@pitt.educurran
Committee MemberFloreancig, Paul E.florean@pitt.eduflorean
Committee MemberEdwards, W. Barryedwardsw@upmc.eduedwardsw
Date: 31 January 2018
Date Type: Publication
Defense Date: 17 October 2016
Approval Date: 31 January 2018
Submission Date: 21 November 2017
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Number of Pages: 201
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: splicing inhibitors, anti-cancer, enansioselective reduction of ketone, fluorescence, sensors, reactive oxygen species
Date Deposited: 31 Jan 2018 14:13
Last Modified: 31 Jan 2018 14:13
URI: http://d-scholarship.pitt.edu/id/eprint/33406

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