Korner, C and Raiber, EA and Keegan, SEM and Nicolau, DC and Sheppard, TD and 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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