|
|||||
|
|
Theoretical modeling of the nonenzymatic solvolysis of CMP-NeuAc in an acidic environment |
|
| Authors: | Bartosz Trzaskowski Andrzej Le Abraham F Jalbout Ludwik Adamowicz Per EM Siegbahn |
| Institution: | aFaculty of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland bDepartment of Chemistry, University of Arizona, Tucson, AZ 85721, USA cInstitute of Chemistry, National Autonomous University of Mexico, Mexico City, Mexico dDepartment of Physics, Stockholm Centre for Physics, Astronomy and Biotechnology (SCFAB), Stockholm University, S-106 91 Stockholm, Sweden |
| Abstract: | A density-functional-theory investigation of the nonenzymatic solvolysis of the cytydine 5′-monophosphate N-acetylneuraminic acid and its derivatives in the acidic environment is presented. The theoretical calculations of the second stage of the reaction mechanism are in agreement with the hypothesis of a dissociative oxocarbenium-like transition state with proton transfer as a key part of the reaction. The geometries of the transition states of the reactions yielding  -methyl and β-methyl glycosides are essentially different. This study provides new theoretical data that can be helpful in elucidating the mechanism of the carbohydrates hydrolysis as well as other reactions catalyzed by the glycosyltransferases. |
| Keywords: | CMP-NeuAc Solvolysis Sialic acid Sialyltransferase DFT |
| 本文献已被 ScienceDirect 等数据库收录！ | |