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New synthesis of cis 5-tert-butyl-L-proline via cuprate. Evaluation as a cis proline mimetic in a biological active octapeptide

✍ Scribed by Carine Aubry; Hassan Oulyadi; Guillaume Dutheuil; Jerome Leprince; Hubert Vaudry; Xavier Pannecoucke; Jean-Charles Quirion


Book ID
105360508
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
293 KB
Volume
12
Category
Article
ISSN
1075-2617

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✦ Synopsis


Abstract

cis 5‐tert‐butyl‐L‐proline (Cbp) was prepared rapidly and efficiently by the addition of low‐valent tert‐butyl cuprate to an aminal derived from proline. [Cbp^2^, D‐Leu^5^]‐OP was then synthesized, showing a predominant cis peptide bond conformation, as confirmed by NMR. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.