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

ABSTRACT: 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.

SUBMITTER: O'Rourke NF

PROVIDER: S-EPMC5633828 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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

O'Rourke Natasha F NF A Mu M Higgs Henry N HN Eastman Alan A Micalizio Glenn C GC

Organic letters 20170913 19

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 pre ...[more]

PMID: 28901150

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