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Synthesis of peptide aldehydes on solid support using ozonolysis

✍ Scribed by Marielle Paris; annie Heitz; Vincent Guerlavais; Michèle Cristau; Jean-Alain Fehrentz; Jean Martinez


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
204 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


A new strategy for the synthesis of peptide aldehydes on solid support is presented. Reaction of a N-protected or-amino aldehyde with MBHA-supported Wittig ou Winig-Horner reagent yielded resin-linked ~-~-unsaturated 8-amino derivative. After elongation of the peptide chain, ozonolysis produced fairly pure C-terminal peptide aldehydes in good yield.


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An efficient method for the solid phase synthesis of aspartyl aldehyde peptides has been developed. It uses a low cost synthetic process for the preparation of Fmoc-protected Weinreb amide linker. This procedure covers several tetrapeptide aspartyl aldehydes as well as biotinylated tetrapeptide aspa