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The stereospecific synthesis of 'orthogonally' protected lanthionines

Swali, V., Matteucci, M., Elliot, R. and Bradley, M. (2002) The stereospecific synthesis of 'orthogonally' protected lanthionines Tetrahedron, 58, (44), pp. 9101-9109. (doi:10.1016/S0040-4020(02)01091-8).

Record type: Article

Abstract

Lanthionine is an attractive monomer for the design and synthesis of novel conformationally constrained peptidomimetics, since unlike cystine, the monosulfur bridge of lanthionine is chemically far more robust and also displays a greater degree of conformational rigidity. The synthesis of lanthionine residues for use in peptide synthesis is non-trivial due to the protectional requirements necessary for this tetra-functional amino acid. In this paper an efficient stereo-specific route to orthogonally protected lanthionine is described.

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More information

Published date: 28 October 2002
Keywords: lanthionine, peptidomimetics, peptides organic sulfur chemistry, solid-phase synthesis, amino-acids, selectivedesulfurization, peptide-synthesis, n-tritylserine, derivatives, analogs, serine, esters

Identifiers

Local EPrints ID: 19864
URI: http://eprints.soton.ac.uk/id/eprint/19864
ISSN: 0040-4020
PURE UUID: 0b21cc1e-364a-4fdf-967f-86df5539732f

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Date deposited: 17 Feb 2006
Last modified: 17 Jul 2017 16:30

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Contributors

Author: V. Swali
Author: M. Matteucci
Author: R. Elliot
Author: M. Bradley

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