A tetradecapeptide somatostatin dicarba-analog: Synthesis, structural impact and biological activity

Bioorganic & Medicinal Chemistry Letters
Pablo Martín-GagoAntoni Riera

Abstract

We described here the first tetradecapeptide somatostatin-analogue where the disulfide bridge has been replaced by a carbon-carbon double bond. This analogue was prepared using microwave assisted ring closing metathesis (RCM) using the 2nd generation Grubbs as catalyst. Under our optimized conditions the cyclization between allylGly 3 and 14 proceeded in moderate yield, excellent cyclic/linear ratio and very high Z-double bond selectivity. NMR studies also demonstrated that the conformational flexibility of this peptide is increased in comparison to that of the natural hormone. Remarkably, this alkene-bridged somatostatin analog is highly selective against somatostatin receptors 1 and 5, suggesting that conformational rigidity is not required for the efficient interaction of somatostatin analogues with these two receptors.

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Citations

May 10, 2015·Pharmacology & Therapeutics·Uma RaiSimon A Young
Aug 19, 2015·The Journal of Organic Chemistry·James BurnleyAndrea J Robinson
Aug 16, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mohsine DriowyaRachid Benhida
Feb 20, 2016·Chemical Communications : Chem Comm·Ellen C GleesonAndrea J Robinson
Jul 28, 2017·Chemistry : a European Journal·Alessandro GoriSilvia Rinaldi
Apr 28, 2021·Journal of Chemical Information and Modeling·Yunhui GeVincent A Voelz
Apr 24, 2014·Journal of Chemical Information and Modeling·Asghar M RazaviVincent A Voelz
Aug 28, 2021·RSC Medicinal Chemistry·Clément Bechtler, Christina Lamers

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