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https://hdl.handle.net/2440/51869
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Type: | Journal article |
Title: | Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates |
Author: | Vernall, A. Ballet, S. Abell, A. |
Citation: | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2008; 64(18):3980-3997 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2008 |
ISSN: | 0040-4020 |
Statement of Responsibility: | Andrea J. Vernall, Steven Ballet, Andrew D. Abell |
Abstract: | Olefin tethers of variable length, introduced into a natural amino acid (side-chain of Ser, Cys; N-terminus of Arg; C-terminus of Phe and Tic; and in both the side-chain and either the N- or C-terminus of Ser, Cys and Tyr), undergo metathesis on treatment with Grubbs' second generation catalyst. Side-chain linked dimers of Ser, Cys and Tyr were obtained by cross-metathesis, while olefin installation at the N- and C-terminus led to dimers of Arg and Phe (or Tic), respectively. Ring-closing metathesis of the doubly alkenylated derivatives of Ser, Cys and Tyr gave 12-, 20- and 24-membered macrocycles. © 2008 Elsevier Ltd. All rights reserved. |
Keywords: | Cross-metathesis (CM) Ring-closing metathesis (RCM) Amino acid dimerization Cyclic amino acids |
DOI: | 10.1016/j.tet.2008.02.043 |
Published version: | http://dx.doi.org/10.1016/j.tet.2008.02.043 |
Appears in Collections: | Aurora harvest 5 Chemistry publications |
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