Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

Boris Aillard; Naomi S. Robertson; Adam R. Baldwin; Siobhan Robins; Andrew G. Jamieson

doi:10.1039/C4OB01832J

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Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides†

Boris Aillard,^a Naomi S. Robertson,^a Adam R. Baldwin,^a Siobhan Robins^a and Andrew G. Jamieson*^a

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^a Department of Chemistry, University of Leicester, Leicester, LE1 7RH, UK
E-mail: andrew.jamieson@le.ac.uk
Fax: +44 (0)116252 3789
Tel: +44 (0)116 252 2105

Abstract

The efficient asymmetric synthesis of unnatural alkenyl amino acids required for peptide ‘stapling’ has been achieved using alkylation of a fluorine-modified Ni^II Schiff base complex as the key step.

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DOI: https://doi.org/10.1039/C4OB01832J
Article type: Paper
Submitted: 27 Aug 2014
Accepted: 16 Sep 2014
First published: 16 Sep 2014

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Org. Biomol. Chem., 2014,12, 8775-8782

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Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

B. Aillard, N. S. Robertson, A. R. Baldwin, S. Robins and A. G. Jamieson, Org. Biomol. Chem., 2014, 12, 8775 DOI: 10.1039/C4OB01832J

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Organic & Biomolecular Chemistry

Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides†

Abstract

Supplementary files

Article information

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Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

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