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Influence of silaproline on peptide conformation and bioactivity.

Journal of the American Chemical Society (2002-03-21)
Florine Cavelier, Bertrand Vivet, Jean Martinez, André Aubry, Claude Didierjean, André Vicherat, Michel Marraud
ABSTRACT

The analogue gamma-(dimethylsila)-proline, denoted silaproline (Sip), was synthesized in both enantiomerically pure forms by diastereoselective alkylation of a chiral glycine equivalent with use of Schöllkopf's bis-lactim ether method. The effect of replacing a proline residue in model peptides by this new proline surrogate has been examined in the crystal state by X-ray diffraction and in solution by IR absorption and NMR techniques. Silaproline and proline-containing sequences exhibit very similar conformational properties. Silaproline was also substituted for proline in a neurotensin (8-13) analogue that retained biological activity and exhibited enhanced resistance to biodegradation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Neurotensin Fragment 8-13 acetate salt, ≥97% (HPLC)