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

✍ Scribed by Cindy Körner; Eun-Ang Raiber; Samuel E.M. Keegan; Daniel C. Nicolau; Tom D. Sheppard; Alethea B. Tabor

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 263 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.09.119

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✦ Synopsis

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.

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