EXPERIMENTAL AND THEORETICAL EVIDENCES OF CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - NMR ANALYSIS AND MOLECULAR MECHANICS CALCULATIONS OFC-LACTOSE AND ITS O-ANALOG

Authors
ESPINOSA JF MARTINPASTOR M ASENSIO JL DIETRICH H MARTINLOMAS M SCHMIDT RR JIMENEZBARBERO J
Citation
Jf. Espinosa et al., EXPERIMENTAL AND THEORETICAL EVIDENCES OF CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - NMR ANALYSIS AND MOLECULAR MECHANICS CALCULATIONS OFC-LACTOSE AND ITS O-ANALOG, Tetrahedron letters, 36(35), 1995, pp. 6329-6332
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
35
Year of publication
1995
Pages
6329 - 6332
Database
ISI
SICI code
0040-4039(1995)36:35<6329:EATEOC>2.0.ZU;2-T
Abstract
NMR data (NOEs and coupling constants) and MM3 molecular mechanics ca lculations have allowed to demonstrate that the conformational behavio ur of C-lactose is different of its O-analogue. The glycosidic linkage s, particularly the C-aglyconic bond, present a high degree of flexibi lity and, therefore, the conformational entropy of C-lactose is higher than that of its O-counterpart.