Journal article
MM3 MODELING OF ALDOPENTOSE PYRANOSE RINGS
Journal of carbohydrate chemistry, Vol.21(1-2), pp.11-25
05/31/2002
DOI: 10.1081/CAR-120003735
Abstract
MM3 (version 1992, ϵ=3.0) was used to study the ring conformations of d-xylopyranose, d-lyxopyranose and d-arabinopyranose. The energy surfaces exhibit low-energy regions corresponding to chair and skew forms with high-energy barriers between these regions corresponding to envelope and half-chair forms. The lowest energy conformer is
4
C
1
for α- and β-xylopyranose and α- and β-lyxopyranose, and the lowest energy conformer is
1
C
4
for α- and β-arabinopyranose. Only α-lyxopyranose exhibits a secondary low-energy region (
1
C
4
) within 1 kcal/mol of its global minimum. Overall, the results are in good agreement with NMR and crystallographic results. For many of these molecules, skew conformations are found with relatively low energies (2.5 to 4 kcal/mol above lowest energy chair form). The
2
S
O
and
1
C
4
conformers of crystalline benzoyl derivatives of xylopyranose are in secondary low-energy regions on the β-xylopyranose surface, within 3.8 kcal/mol of the global
4
C
1
minimum.
Details
- Title: Subtitle
- MM3 MODELING OF ALDOPENTOSE PYRANOSE RINGS
- Creators
- Michael K. Dowd - Southern Regional Research CenterWilliam M. Rockey - Iowa State UniversityAlfred D. French - Southern Regional Research CenterPeter J. Reilly - Iowa State University
- Resource Type
- Journal article
- Publication Details
- Journal of carbohydrate chemistry, Vol.21(1-2), pp.11-25
- Publisher
- Taylor & Francis Group
- DOI
- 10.1081/CAR-120003735
- ISSN
- 0732-8303
- eISSN
- 1532-2327
- Language
- English
- Date published
- 05/31/2002
- Academic Unit
- Radiation Oncology
- Record Identifier
- 9984313089802771
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