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Kinetic deconjugation: a gateway to the synthesis of Xxx-Gly (E)-alkene dipeptide isosteres |
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| Authors: | Arnaud Proteau-GagnéJean-François Nadon Sylvain BernardBrigitte Guérin Louis Gendron Yves L Dory |
| Institution: | a Laboratoire de Chimie Supramoléculaire, Département de Chimie, Université de Sherbrooke, 3001 12e Av. Nord, Sherbrooke, QC, Canada J1H 5N4 b Département de Médecine Nucléaire et de Radiobiologie, Université de Sherbrooke, 3001 12e Av. Nord, Sherbrooke, QC, Canada J1H 5N4 c Département de Physiologie et Biophysique, Université de Sherbrooke, 3001 12e Av. Nord, Sherbrooke, QC, Canada J1H 5N4 |
| Abstract: | A new method for the preparation of Xxx-Gly (E)-alkene dipeptide isosteres (EADIs), using LDA deprotonation followed by 1 N HCl quench, was explored. The method, named kinetic deconjugation, enabled the synthesis of Tyr-Gly, Gly-Gly, Ser-Gly, Pro-Gly, and Phe-Gly EADIs, as well as one Tyr-Gly trisubstituted alkene dipeptide isostere (TADI). Overall, this method, based on commercially available materials, leads to high yields, requires few synthetic steps and works on the gram scale in the synthesis of a wide variety of EADIs. |
| Keywords: | (E)-Alkene dipeptide isostere Trisubstituted alkene dipeptide isostere (E)-β γ-Unsaturated ester Peptidomimetics Lithium diisopylamine |
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