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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2017
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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. |
format | Online Article Text |
id | pubmed-5633828 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
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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