MM3(96) CONFORMATIONAL ANALYSIS OF d-GLUCARAMIDE AND X-RAY CRYSTAL STRUCTURES OF THREE d-GLUCARIC ACID DERIVATIVES—MODELS FOR SYNTHETIC POLY(ALKYLENE d-GLUCARAMIDES)

Abstract

An exhaustive conformational analysis of d-glucaramide was carried out using MM3(96) [MM3(96). Molecular Mechanics Software used with permission from N.L. Allinger; University of Georgia]. Nine torsion angles were each driven in increments of 120°, generating 19,683 starting conformations. Each conformation was then fully energy-minimized using MM3's block diagonal/full matrix optimization option at dielectric constants of both 3.5 and 6.5. Conformer populations were calculated based on the modeling results and calculated theoretical average 1H vicinal coupling constants were compared to experimental values obtained in D 2O solution. Crystal structures of three acyclic d-glucaric acid derivatives (N, N′-dimethyl- d-glucaramide, dipotassium d-glucarate, and sodium potassium d-glucarate) are reported. These structures and that of previously reported monopotassium glucarate correspond closely with model conformations that were within one kcal/mol of the global minimum.