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Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone

[Image: see text] A chemical foundation for function-oriented studies of pectenotoxin 2 (PTX2) is described. A synthesis of the bicyclic GH-system, and the design and synthesis of a PTX2-analogue, is presented. While maintaining critical features for actin binding, and lacking the Achilles’ heel for...

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Autores principales: O’Rourke, Natasha F., A, Mu, Higgs, Henry N., Eastman, Alan, Micalizio, Glenn C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633828/
https://www.ncbi.nlm.nih.gov/pubmed/28901150
http://dx.doi.org/10.1021/acs.orglett.7b02435
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author O’Rourke, Natasha F.
A, Mu
Higgs, Henry N.
Eastman, Alan
Micalizio, Glenn C.
author_facet O’Rourke, Natasha F.
A, Mu
Higgs, Henry N.
Eastman, Alan
Micalizio, Glenn C.
author_sort O’Rourke, Natasha F.
collection PubMed
description [Image: see text] A chemical foundation for function-oriented studies of pectenotoxin 2 (PTX2) is described. A synthesis of the bicyclic GH-system, and the design and synthesis of a PTX2-analogue, is presented. While maintaining critical features for actin binding, and lacking the Achilles’ heel for the natural product’s anticancer activity (the AB-spiroketal), this first-generation analogue did not possess the anticancer properties of PTX2, an observation that indicates the molecular significance of features present in the natural product’s CDEF-tetracycle.
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spelling pubmed-56338282017-10-11 Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone O’Rourke, Natasha F. A, Mu Higgs, Henry N. Eastman, Alan Micalizio, Glenn C. Org Lett [Image: see text] A chemical foundation for function-oriented studies of pectenotoxin 2 (PTX2) is described. A synthesis of the bicyclic GH-system, and the design and synthesis of a PTX2-analogue, is presented. While maintaining critical features for actin binding, and lacking the Achilles’ heel for the natural product’s anticancer activity (the AB-spiroketal), this first-generation analogue did not possess the anticancer properties of PTX2, an observation that indicates the molecular significance of features present in the natural product’s CDEF-tetracycle. American Chemical Society 2017-09-13 2017-10-06 /pmc/articles/PMC5633828/ /pubmed/28901150 http://dx.doi.org/10.1021/acs.orglett.7b02435 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle O’Rourke, Natasha F.
A, Mu
Higgs, Henry N.
Eastman, Alan
Micalizio, Glenn C.
Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title_full Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title_fullStr Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title_full_unstemmed Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title_short Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone
title_sort function-oriented studies targeting pectenotoxin 2: synthesis of the gh-ring system and a structurally simplified macrolactone
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633828/
https://www.ncbi.nlm.nih.gov/pubmed/28901150
http://dx.doi.org/10.1021/acs.orglett.7b02435
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