eprintid: 33406
rev_number: 9
userid: 490
dir: disk0/00/03/34/06
datestamp: 2018-01-31 14:13:05
lastmod: 2018-01-31 14:13:05
status_changed: 2018-01-31 14:13:05
type: thesis_degree
metadata_visibility: show
contact_email: upb1@pitt.edu
eprint_status: archive
creators_name: Basu, Upamanyu
creators_email: upb1@pitt.edu
creators_id: upb1
title: DEVELOPMENT OF A NEW ENANTIOSELECTIVE REDUCTION OF KETONE AND FLUOROGENIC DETECTION OF HYDROGEN PEROXIDE
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: restricted
keywords: splicing inhibitors, anti-cancer, enansioselective reduction of ketone, fluorescence, sensors, reactive oxygen species
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.
date: 2018-01-31
date_type: published
pages: 201
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Koide, Kazunori
etdcommittee_name: Curran, Dennis P.
etdcommittee_name: Floreancig, Paul E.
etdcommittee_name: Edwards, W. Barry
etdcommittee_email: koide@pitt.edu
etdcommittee_email: curran@pitt.edu
etdcommittee_email: florean@pitt.edu
etdcommittee_email: edwardsw@upmc.edu
etdcommittee_id: koide
etdcommittee_id: curran
etdcommittee_id: florean
etdcommittee_id: edwardsw
etd_defense_date: 2016-10-17
etd_approval_date: 2018-01-31
etd_submission_date: 2017-11-21
etd_release_date: 2018-01-31
etd_access_restriction: 5_year
etd_patent_pending: FALSE
thesis_type: dissertation
degree: PhD
citation:   Basu, Upamanyu  (2018) DEVELOPMENT OF A NEW ENANTIOSELECTIVE REDUCTION OF KETONE AND FLUOROGENIC DETECTION OF HYDROGEN PEROXIDE.  Doctoral Dissertation, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/33406/1/ETD_UB_final_1.pdf