Document Detail


An AM1 molecular orbital study of alpha-D-glucopyranose and beta-maltose: evaluation and implications.
MedLine Citation:
PMID:  8495446     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Chemical reactivity and other characteristics of alpha-D-glucopyranose and beta-maltose were evaluated within a semiempirical molecular orbital (AM1) framework. Theoretically generated structures compared well to those determined by X-ray crystallographic techniques. Calculations suggested that the secondary hydroxy functions (OH-2 and OH-3) of the mono- and di-saccharides were more acidic than the primary alcohol (OH-6), which is consistent with experimental findings. In addition, the enhanced reactivity of the OH-3 locus, which is observed upon OH-2 alkylation of the object sugars, was rationalized in terms of increased OH-3 acidity. The chemical behavior of the monomers examined may be insightful in explaining the reactivity of glucopyranose polymers.
Authors:
M E Brewster; M J Huang; E Pop; J Pitha; M J Dewar; J J Kaminski; N Bodor
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Carbohydrate research     Volume:  242     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1993 Apr 
Date Detail:
Created Date:  1993-06-18     Completed Date:  1993-06-18     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  53-67     Citation Subset:  IM    
Affiliation:
Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville 32610.
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MeSH Terms
Descriptor/Qualifier:
Carbohydrate Conformation
Carbohydrate Sequence
Glucose / chemistry*
Maltose / chemistry*
Models, Molecular
Molecular Sequence Data
Thermodynamics
X-Ray Diffraction
Chemical
Reg. No./Substance:
50-99-7/Glucose; 69-79-4/Maltose

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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