Disaccharide conformational maps: adiabaticity in analogs with variable ring shapes

CARLOS A. STORTZ; ALFRED D. FRENCH

MOLECULAR SIMULATION

Taylor & Francis

Lugar: Londres; Año: 2008 vol. 34 p. 373 - 389

0892-7022

Relaxed MM3 w, c potential energy surfaces (conformational maps) were calculated for analogues of a,a-trehalose,w, c potential energy surfaces (conformational maps) were calculated for analogues of a,a-trehalose, b,b-trehalose, a,b-trehalose, maltose, cellobiose and galabiose based on 2-methyltetrahydropyran. Starting structures included not only 4C1 (sugar nomenclature) geometries, but also combinations with 1C4 conformers, and some flexible (boat or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the included not only 4C1 (sugar nomenclature) geometries, but also combinations with 1C4 conformers, and some flexible (boat or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the ,b-trehalose, a,b-trehalose, maltose, cellobiose and galabiose based on 2-methyltetrahydropyran. Starting structures included not only 4C1 (sugar nomenclature) geometries, but also combinations with 1C4 conformers, and some flexible (boat or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the or skew) forms. These forms were included as part of continuing efforts to eliminate unwarranted assumptions in modelling studies, as well as to account for new experimental findings. Four to nine maps were obtained for each analogue, and from them adiabatic maps were produced. Although the minimum energy regions always resulted from 4C1Z4C1 geometries, moderate to large parts of most maps had lower energies when one or both rings were in the 1C4 conformation. Only the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the adiabatic surface for the (diequatorial) analogue of b,b-trehalose was covered entirely by 4C1Z4C1 conformers. For the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the of the cellobiose analogue surface was covered by conformers having a 1C4 conformation at the "reducing" end, and for the cellobiose and a,b-trehalose analogues, these conformers covered 74 and 67% of the surfaces, respectively. The remainder of the cellobiose analogue surface was covered by conformers having a 1C4