Journal article
Modeling of deoxy- and dideoxyaldohexopyranosyl ring puckering with MM3(92)
Carbohydrate research, Vol.335(4), pp.261-273
2001
DOI: 10.1016/S0008-6215(01)00240-3
PMID: 11595220
Abstract
Extensive variations of the ring structures of three deoxyaldohexopyranoses,
l-fucose,
d-quinovose, and
l-rhamnose, and four dideoxyaldohexopyranoses,
d-digitoxose, abequose, paratose, and tyvelose, were studied by energy minimization with the molecular mechanics algorithm
MM3(92). Chair conformers,
4
C
1 in
d-quinovose and the equivalent
1
C
4 in
l-fucose and
l-rhamnose, overwhelmingly dominate in the three deoxyhexoses; in the
d-dideoxyhexoses,
4
C
1 is again dominant, but with increased amounts of
1
C
4 forms in the α anomers of the three 3,6-dideoxyhexoses, abequose, paratose, and tyvelose and in both α and β anomers of the 2,6-dideoxyhexose
d-digitoxose. In general, modeled proton–proton coupling constants agreed well with experimental values. Computed anomeric ratios strongly favor the β configuration except for
d-digitoxose, which is almost equally divided between α and β configurations, and
l-rhamnose, where the β configuration is somewhat favored.
MM3(92) appears to overstate the prevalence of the equatorial β anomer in all three deoxyhexoses, as earlier found with fully oxygenated aldohexopyranoses.
MM3(92) molecular modeling of seven deoxy- and dideoxyaldohexopyranoses allowed assignment of conformational ring forms, and the computed proton–proton coupling constants in general agreed with the experimental values.
Details
- Title: Subtitle
- Modeling of deoxy- and dideoxyaldohexopyranosyl ring puckering with MM3(92)
- Creators
- William M Rockey - Department of Chemical Engineering, Iowa State University, Ames, IA 50011, USAMichael K Dowd - Southern Regional Research Center, U.S. Department of Agriculture, New Orleans, LA 70179, USAPeter J Reilly - Department of Chemical Engineering, Iowa State University, Ames, IA 50011, USAAlfred D French - Southern Regional Research Center, U.S. Department of Agriculture, New Orleans, LA 70179, USA
- Resource Type
- Journal article
- Publication Details
- Carbohydrate research, Vol.335(4), pp.261-273
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/S0008-6215(01)00240-3
- PMID
- 11595220
- ISSN
- 0008-6215
- eISSN
- 1873-426X
- Language
- English
- Date published
- 2001
- Academic Unit
- Radiation Oncology
- Record Identifier
- 9984047870002771
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