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Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates |
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| Authors: | Andrea J. Vernall Andrew D. Abell |
| Affiliation: | a Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand b Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium c School of Chemistry and Physics, University of Adelaide, North Terrace, Adelaide, SA 5005, Australia |
| 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. |
| Keywords: | Cross-metathesis (CM) Ring-closing metathesis (RCM) Amino acid dimerization Cyclic amino acids |
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