Literature DB >> 15987180

Ring-closing alkyne metathesis approach toward the synthesis of alkyne mimics of thioether A-, B-, C-, and DE-ring systems of the lantibiotic nisin Z.

Nourdin Ghalit1, Alex J Poot, Alois Fürstner, Dirk T S Rijkers, Rob M J Liskamp.   

Abstract

[reaction: see text] Ring-closing alkyne metathesis toward the synthesis of the alkyne-brigded A-, B-, C-, and (D)E-ring mimics of the peptide antibiotic nisin Z is described. We have successfully synthesized alkyne-bridged cyclic peptides containing 4-7 amino acid residues in yields ranging from 18 to 82%.

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Year:  2005        PMID: 15987180     DOI: 10.1021/ol0508781

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  All-atom model for stabilization of alpha-helical structure in peptides by hydrocarbon staples.

Authors:  Peter S Kutchukian; Jae Shick Yang; Gregory L Verdine; Eugene I Shakhnovich
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

2.  The Ascent of Alkyne Metathesis to Strategy-Level Status.

Authors:  Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-09-14       Impact factor: 15.419

3.  Orthogonal ring-closing alkyne and olefin metathesis for the synthesis of small GTPase-targeting bicyclic peptides.

Authors:  Philipp M Cromm; Sebastian Schaubach; Jochen Spiegel; Alois Fürstner; Tom N Grossmann; Herbert Waldmann
Journal:  Nat Commun       Date:  2016-04-14       Impact factor: 14.919

4.  Canopy Catalysts for Alkyne Metathesis: Investigations into a Bimolecular Decomposition Pathway and the Stability of the Podand Cap.

Authors:  Julius Hillenbrand; J Nepomuk Korber; Markus Leutzsch; Nils Nöthling; Alois Fürstner
Journal:  Chemistry       Date:  2021-08-26       Impact factor: 5.236

  4 in total

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