| An AM1 molecular orbital study of alpha-D-glucopyranose and beta-maltose: evaluation and implications. | |
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MedLine Citation:
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PMID: 8495446 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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M E Brewster; M J Huang; E Pop; J Pitha; M J Dewar; J J Kaminski; N Bodor |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Carbohydrate research Volume: 242 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 1993 Apr |
Date Detail:
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Created Date: 1993-06-18 Completed Date: 1993-06-18 Revised Date: 2000-12-18 |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 53-67 Citation Subset: IM |
Affiliation:
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Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville 32610. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Carbohydrate Conformation Carbohydrate Sequence Glucose / chemistry* Maltose / chemistry* Models, Molecular Molecular Sequence Data Thermodynamics X-Ray Diffraction |
| Chemical | |
Reg. No./Substance:
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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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