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.
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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.
J Pept Sci
February 2006
Laboratoire d'Hétérochimie Organique, UMR CNRS 6014, IRCOF, INSA et Université de Rouen, F-76821 Mont-Saint-Aignan, France.
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.
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