A re-optimized GROMOS force field for hexopyranose-based carbohydrates accounting for the relative free energies of ring conformers, anomers, epimers, hydroxymethyl rotamers, and glycosidic linkage conformers was written by Hansen, Halvor S.;Huenenberger, Philippe H.. And the article was included in Journal of Computational Chemistry in 2011.Electric Literature of C6H12O2 This article mentions the following:
This article presents a re-optimization of the GROMOS 53A6 force field for hexopyranose-based carbohydrates (nearly equivalent to 45A4 for pure carbohydrate systems) into a new version 56ACARBO (nearly equivalent to 53A6 for non-carbohydrate systems). This re-optimization was found necessary to repair a number of short-comings of the 53A6 (45A4) parameter set and to extend the scope of the force field to properties that had not been included previously into the parameterization procedure. The new 56ACARBO force field is characterized by: (i) the formulation of systematic build-up rules for the automatic generation of force-field topologies over a large class of compounds including (but not restricted to) un-functionalized poly-hexopyranoses with arbritrary connection; (ii) the systematic use of enhanced sampling methods for inclusion of exptl. thermodn. data concerning slow or un-phys. processes into the parameterization procedure; and (iii) an extensive validation against available exptl. data in solution and, to a limited extent, theor. (quantum-mech.) data in the gas phase. At present, the 56ACARBO force field is restricted to compounds of the elements C, O, and H presenting single bonds only, no oxygen functions other than alc., ether, hemiacetal, or acetal, and no cyclic segments other than six-membered rings (separated by at least one intermediate atom). After calibration, this force field is shown to reproduce well the relative free energies of ring conformers, anomers, epimers, hydroxymethyl rotamers, and glycosidic linkage conformers. As a result, the 56ACARBO force field should be suitable for: (i) the characterization of the dynamics of pyranose ring conformational transitions (in simulations on the microsecond timescale); (ii) the investigation of systems where alternative ring conformations become significantly populated; (iii) the investigation of anomerization or epimerization in terms of free-energy differences; and (iv) the design of simulation approaches accelerating the anomerization process along an un-phys. pathway. © 2010 Wiley Periodicals, Inc. J Comput Chem, 2011. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4Electric Literature of C6H12O2).
2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Electric Literature of C6H12O2
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics