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

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. [Cbp2, D‐Leu5]‐OP was then synthesized, showing a predominant cis peptide bond conformation, as confirmed by NMR. Copyright © 2005 European Peptid...

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Bibliographic Details
Published in:Journal of peptide science 2006-02, Vol.12 (2), p.154-160
Main Authors: Aubry, Carine, Oulyadi, Hassan, Dutheuil, Guillaume, Leprince, Jerome, Vaudry, Hubert, Pannecoucke, Xavier, Quirion, Jean-Charles
Format: Article
Language:English
Subjects:
acyliminium
Copper - chemistry
cuprate
Molecular Mimicry
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides - chemistry
Oligopeptides - isolation & purification
Oligopeptides - pharmacology
peptide conformation
peptide mimic
Proline - analogs & derivatives
Proline - chemical synthesis
proline analogue
tert-butyl proline
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Summary: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. [Cbp2, D‐Leu5]‐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.
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.690