| Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides. | |
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MedLine Citation:
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PMID: 14698880 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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To facilitate the use of oligosaccharides as analytical tools in biological studies, we have designed, synthesized, and conjugated to maltosaccharides a novel series of homologous small fluorescent moieties that differ in formal charge. These moieties are amide derivatives of anthranilic acid: uncharged N-(2-aminobenzoyl)glycinamide (ABGlyAmide; 2), acidic N,N-dimethyl-N(')-(2-aminobenzoyl)ethylenediamine (ABGlyDIMED; 3), and basic N-(2-aminobenzoyl)glycine (ABGly; 1). Routes for synthesis and optimal reaction conditions for glycoconjugation by conventional reductive amination are presented, as is the compatibility of these adducts with common analytical and preparative chromatographic methods, including RP-HPLC and HPAEC-PAD. These novel anthranilic acid derivatives confer both fluorescence and defined charge to oligosaccharides, and so enhance the repertoire of chromatographic and analytical methods for which anthranilic acid can be used. Furthermore, because glucosaccharides have rigid solution structure, these small fluorescent adducts with different formal charge are ideal tools for molecular sizing studies of membrane pores. |
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Authors:
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Darren Locke; Carville G Bevans; Lai Xi Wang; Ye Zhang; Andrew L Harris; Yuan C Lee |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Carbohydrate research Volume: 339 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2004 Jan |
Date Detail:
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Created Date: 2003-12-30 Completed Date: 2004-09-16 Revised Date: 2008-11-21 |
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: 221-31 Citation Subset: IM |
Affiliation:
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Department of Pharmacology and Physiology, New Jersey Medical School, UMDNJ, 185 South Orange Avenue, Newark, NJ 07103, USA. lockeda@umdnj.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acids
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chemistry Adsorption Amines / chemistry Anthranilic Acids / chemical synthesis, chemistry* Carbohydrate Conformation Hydrogen-Ion Concentration Ions / chemistry Molecular Structure Oligosaccharides / chemistry*, isolation & purification Oxidation-Reduction Solutions / chemistry Spectrum Analysis Static Electricity |
| Grant Support | |
ID/Acronym/Agency:
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DK009970/DK/NIDDK NIH HHS; GM36044/GM/NIGMS NIH HHS; GM61406/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Acids; 0/Amines; 0/Anthranilic Acids; 0/Ions; 0/Oligosaccharides; 0/Solutions; 88-68-6/anthranilamide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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