Conformational analysis of levanbiose by molecular mechanics

Abstract

A relaxed conformational energy map for levanbiose, O-β- d-fructofuranosyl-(2 → 6)-β- d-fructofuranoside, was computed with the molecular mechanics program MM2(87). All torsion angles of the three linkage bonds were driven by 30° increments while two primary alcohol groups were held at three staggered forms. The steric energy of all other parameters was optimized. The side groups were retained at the same relative positions on the two rings in this first part of the study so our results are directly applicable to the study of polymeric levan with identical repeating units. The low-energy dimers did not lead to viable polymers. The interresidue linkage torsion angles defined by C-6O-′2C-2′C-′1 (φ) and O-5C-5C-6O′2 (ω) have minima at +60° and −60°, respectively, with accessible minima at other staggered forms. As observed in inulobiose, the preferred torsion angle at central linkage bond defined by C-5C-6O-2′C-2′2 (ψ) was antiperiplanar. An analysis of all conformations of staggered side groups showed that the C-1 and C-1′ groups had little effect but the C-6′ group showed a preference for X -6′(O-5′C-5′C-6′O-6′) = −60°. The fructofuranose rings were started at the low-energy 4 3 T conformation (angle of pseudorotation, φ 2 = 265°) that was retained except when the linkage conformations created severe inter-residue conflict.