Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates

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dc.contributor.authorVernall, A.
dc.contributor.authorBallet, S.
dc.contributor.authorAbell, A.
dc.date.issued2008
dc.description.abstractOlefin 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.
dc.description.statementofresponsibilityAndrea J. Vernall, Steven Ballet, Andrew D. Abell
dc.identifier.citationTetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2008; 64(18):3980-3997
dc.identifier.doi10.1016/j.tet.2008.02.043
dc.identifier.issn0040-4020
dc.identifier.orcidAbell, A. [0000-0002-0604-2629]
dc.identifier.urihttp://hdl.handle.net/2440/51869
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.source.urihttps://doi.org/10.1016/j.tet.2008.02.043
dc.subjectCross-metathesis (CM)
dc.subjectRing-closing metathesis (RCM)
dc.subjectAmino acid dimerization
dc.subjectCyclic amino acids
dc.titleCross-metathesis and ring-closing metathesis reactions of amino acid-based substrates
dc.typeJournal article
pubs.publication-statusPublished

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