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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 LETT , 51 (49) 6381 - 6383. 10.1016/j.tetlet.2010.09.119.

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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
DOI: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 > Chemistry

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