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)

• Published in: Journal of carbohydrate chemistry Vol. 21; no. 1-2; pp. 27 - 51
• Main Authors: Styron, Susan D., French, Alfred D., Friedrich, Joyce D., Lake, Charles H., Kiely, Donald E.
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 31.05.2002
• ISSN: 0732-8303; 1532-2327
• DOI: 10.1081/CAR-120003736

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 1 H vicinal coupling constants were compared to experimental values obtained in D 2 O 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.