Citation
Proteau, Philip Jerome (1990) Neocarzinostatin chromophore: structural, mechanistic, and synthetic studies. Master's thesis, California Institute of Technology. doi:10.7907/tmh7-8559. https://resolver.caltech.edu/CaltechTHESIS:08122014-131021849
Abstract
Neocarzinostatin chromophore 1 is the active component of the antitumor antibiotic neocarzinostatin (NCS). The chromophore reacts with thiols to form a highly strained cumulene-enyne species which rapidly rearranges to a biradical intermediate which can abstract hydrogen atoms from DNA, leading to strand cleavage. DNA damage is the proposed source of biological activity for NCS. The structure of the methyl thioglycolate monoadduct 2 of NCS chromophore, including the absolute stereochemistry, was determined by NMR studies. The presence of the cumulene-enyne intermediate and the rearrangement to a biradical were supported by data from low temperature NMR investigations. Also included are synthetic approaches to NCS chromophore model compounds based on intramolecular addition of an acetylide to an aldehyde.
Item Type: | Thesis (Master's thesis) |
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Subject Keywords: | Chemistry |
Degree Grantor: | California Institute of Technology |
Division: | Chemistry and Chemical Engineering |
Major Option: | Chemistry |
Thesis Availability: | Public (worldwide access) |
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Thesis Committee: |
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Defense Date: | 23 October 1989 |
Record Number: | CaltechTHESIS:08122014-131021849 |
Persistent URL: | https://resolver.caltech.edu/CaltechTHESIS:08122014-131021849 |
DOI: | 10.7907/tmh7-8559 |
Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. |
ID Code: | 8633 |
Collection: | CaltechTHESIS |
Deposited By: | Benjamin Perez |
Deposited On: | 14 Aug 2014 20:47 |
Last Modified: | 09 Nov 2022 19:20 |
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