Strategies and methods for the synthesis of paralytic shellfish poisons

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Voltage-gated sodium ion channels are integral membrane proteins most commonly associated with the propagation of action potentials along electrically conducting cells. Nine distinct mammalian isoforms exist, which vary in their primary sequence, gating properties and tissue distribution. Efforts to deconvolute the physiological roles of each isoform through genetic methods, including knockout and gene silencing, are complicated by issues of redundancy and compensatory upregulation of related isoforms. Here we present new strategies and methods for the synthesis of a class of small molecule sodium channel inhibitors, the paralytic shellfish poisons. Methods for the construction of cyclic 5-membered guanidines from acyclic precursors through intramolecular C--H amination and a total synthesis of the paralytic shellfish poison (+)-gonyautoxin 3 are described. It is our vision that these developments will ultimately lead to new small molecule probes designed to help answer fundamental questions regarding sodium ion channel structure and diversity.


Type of resource text
Form electronic; electronic resource; remote
Extent 1 online resource.
Publication date 2010
Issuance monographic
Language English


Associated with Mulcahy, John Vincent
Associated with Stanford University, Department of Chemistry
Primary advisor Du Bois, Justin
Thesis advisor Du Bois, Justin
Thesis advisor Kool, Eric T
Thesis advisor Wender, Paul A
Advisor Kool, Eric T
Advisor Wender, Paul A


Genre Theses

Bibliographic information

Statement of responsibility John Vincent Mulcahy.
Note Submitted to the Department of Chemistry.
Thesis Thesis (Ph. D.)--Stanford University, 2010.
Location electronic resource

Access conditions

© 2010 by John Vincent Mulcahy

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