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Neocarzinostatin chromophore: structural, mechanistic, and synthetic studies


Proteau, Philip Jerome (1990) Neocarzinostatin chromophore: structural, mechanistic, and synthetic studies. Master's thesis, California Institute of Technology. doi:10.7907/tmh7-8559.


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)
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Unknown, Unknown
Thesis Committee:
  • Unknown, Unknown
Defense Date:23 October 1989
Record Number:CaltechTHESIS:08122014-131021849
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:8633
Deposited By: Benjamin Perez
Deposited On:14 Aug 2014 20:47
Last Modified:09 Nov 2022 19:20

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