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Nad(P)+-nad(p)h models. 57 : Stereochemistry in (net) hydride transfer from and to nad(p)+-nad(p)h models: chirality sink
Affiliation:1. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;2. Department of Chemistry, College of Science & Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia;3. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt;4. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, Tamil Nadu 625 021, India;5. Central Laboratory, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;6. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia;7. Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt;8. Department of Chemistry, Vivekanandha College of Arts and Sciences for Women (Autonomous), Elayampalayam, Namakkal, Tamil Nadu 637 205, India;1. College of Chemistry, Jilin University, Changchun 130012, PR China;2. Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130012, PR China;1. Department of Pharmacology, School of Basic Medical Sciences, Shandong University, Jinan, 250012, China;2. Department of Clinical Pharmacy, Qilu Hospital of Shandong University, Jinan, 250012, China;3. School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China;4. Department of Neurosurgery, Provincial Hospital, Shandong University, Jinan, 250021, China
Abstract:NAD(P)H/NAD(P)+ and related compounds have intrinsic chirality against the axis alone the C3–Ccarbonyl single bond. A model compound which has a stable conformation with respect to this chirality was synthesized and the conformational relationship between the carbonyl dipole and the reacting hydrogen was studied. It has been concluded that there is a relationship between conformations of these groups both in reduction and in oxidation provided the substrate is a neutral species. The result is discussed in relation with the hypothesis proposed previously on the basis of quantum chemical calculations.
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