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An expedient synthesis of orthogonally protected lysinoalanine from Aloc-protected Garner's aldehyde

Korner, C; Raiber, EA; Keegan, SEM; Nicolau, DC; Sheppard, TD; Tabor, AB; (2010) An expedient synthesis of orthogonally protected lysinoalanine from Aloc-protected Garner's aldehyde. Tetrahedron Letters , 51 (49) 6381 - 6383. 10.1016/j.tetlet.2010.09.119. Green open access

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Abstract

An expedient synthesis of orthogonally protected lysinoalanine has been developed. We have prepared a novel Garner's aldehyde derivative bearing an Aloc group; reductive amination of this aldehyde with Fmoc-Lys-OPMB gave the lysinoalanine skeleton. This was then transformed into an orthogonally protected lysinoalanine derivative suitable for the synthesis of side-chain bridged cyclic peptides by solid phase peptide synthesis methods. (C) 2010 Elsevier Ltd. All rights reserved.

Type: Article
Title: An expedient synthesis of orthogonally protected lysinoalanine from Aloc-protected Garner's aldehyde
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tetlet.2010.09.119
Publisher version: http://dx.doi.org/10.1016/j.tetlet.2010.09.119
Language: English
Additional information: “NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, VOL 51, ISSUE 49, 2010 http://dx.doi.org/10.1016/j.tetlet.2010.09.119
Keywords: Garner's aldehyde, Lantibiotic, Lysinoalanine, Reductive amination, Cinnamycin, Alpha-amino aldehydes, Solid-phase synthesis, Enantioselective synthesis, Straightforward synthesis, Beta-methyllanthionine, Building-blocks, Peptide, Lanthionines, Acids, Serine
UCL classification: UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/643979
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