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  Total Synthesis and Evaluation of the Actin-Binding Properties of Microcarpalide and a Focused Library of Analogues

Fürstner, A., Nagano, T., Müller, C., Seidel, G., & Müller, O. (2007). Total Synthesis and Evaluation of the Actin-Binding Properties of Microcarpalide and a Focused Library of Analogues. Chemistry – A European Journal, 13(3), 1452-1462. doi:10.1002/chem.200601370.

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 Creators:
Fürstner, Alois1, Author              
Nagano, Takashi1, Author              
Müller, Christoph1, Author              
Seidel, Günter1, Author              
Müller, Oliver2, Author
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Max-Planck-Institut für Molekulare Physiologie, 44227 Dortmund, Germany, ou_persistent22              

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Free keywords: actin; lactones; medium-sized rings; metathesis; natural products
 Abstract: A comparative investigation shows that hydroxylated 10-membered lactones modeled around the fungal metabolites microcarpalide (1) and pinolidoxin (2) are endowed with selective actin-binding properties. Although less potent than the marine natural product latrunculin A, which represents the standard in the field, nonenolides of this type are significantly less toxic and accommodate substantial structural editing. Most notable is the fact that even an intramolecular transesterification with formation of a hydroxylated butanolide skeleton does not annihilate their microfilament disrupting capacity. This finding calls for a reinvestigation of the biological profile of other fungal metabolites that embody a similar motif. Microcarpalide (1) serving as the calibration point for this comparative study was prepared by total synthesis based on ring-closing metathesis (RCM) as the key step. The chosen route favorably compares to previous approaches to this target and provides further support for the notion that the (E,Z)-configuration of a medium-sized cycloalkene can be controlled by proper choice of the catalyst as previously outlined by our group. 9-epi-Microcarpalide 26 and furanone 27 as representative examples of the “natural productlike” compounds investigated herein have been characterized by crystal structure analysis.

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Language(s): eng - English
 Dates: 2006-09-242006-11-242007-02-02
 Publication Status: Published in print
 Pages: 11
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.200601370
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 13 (3) Sequence Number: - Start / End Page: 1452 - 1462 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058