Martí-Centelles Vicente, Burguete M Isabel, Luis Santiago V
Departamento de Química Inorgánica y Orgánica, Universitat Jaume I , Avenida de Vicent Sos Baynat s/n, 12071 Castellón, Spain.
J Org Chem. 2016 Mar 4;81(5):2143-7. doi: 10.1021/acs.joc.5b02676. Epub 2016 Feb 11.
A new family of pseudopeptidic macrocyclic compounds has been prepared involving an anion-templated amide bond formation reaction at the macrocyclization step. Chloride anion was found to be the most efficient template in the macrocyclization process, producing improved macrocyclization yields with regard to the nontemplated reaction. The data suggest a kinetic effect of the chloride template, providing an appropriate folded conformation of the open-chain precursor and reducing the energy barrier for the formation of the macrocyclic product.
已经制备了一类新的拟肽大环化合物，其在大环化步骤中涉及阴离子模板化的酰胺键形成反应。发现氯离子是大环化过程中最有效的模板，与非模板反应相比，可提高大环化产率。数据表明氯离子模板具有动力学效应，能提供开链前体合适的折叠构象并降低大环产物形成的能量屏障。
