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Issue 6, 2007
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Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis

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Abstract

This paper describes two approaches for the synthesis of a crossed alkene-bridged mimic of the thioether ring system of the nisin Z DE-fragment. The first approach comprised the stepwise total synthesis featuring a cross metathesis and a macrolactamization on a solid support followed by a ring-closing metathesis in solution. Via this route the title compound was obtained in an overall yield of 7% (85% on average for 16 reaction steps). In the second approach, the linear precursor peptide was subjected to ring-closing metathesis and the bicyclic peptide with the correct side chain connectivity pattern was obtained in yields up to 95%. The preferred formation of the bicyclic crossed alkene-bridged mimic of the DE-ring suggests a favorable pre-organization of the linear precursor peptide.

Graphical abstract: Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis

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Article information


Submitted
12 Dec 2006
Accepted
16 Jan 2007
First published
07 Feb 2007

Org. Biomol. Chem., 2007,5, 924-934
Article type
Paper

Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis

N. Ghalit, J. Kemmink, H. W. Hilbers, C. Versluis, D. T. S. Rijkers and R. M. J. Liskamp, Org. Biomol. Chem., 2007, 5, 924 DOI: 10.1039/B618085J

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