Document Detail


Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides.
MedLine Citation:
PMID:  14698880     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Darren Locke; Carville G Bevans; Lai Xi Wang; Ye Zhang; Andrew L Harris; Yuan C Lee
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Carbohydrate research     Volume:  339     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2004 Jan 
Date Detail:
Created Date:  2003-12-30     Completed Date:  2004-09-16     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  221-31     Citation Subset:  IM    
Affiliation:
Department of Pharmacology and Physiology, New Jersey Medical School, UMDNJ, 185 South Orange Avenue, Newark, NJ 07103, USA. lockeda@umdnj.edu
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MeSH Terms
Descriptor/Qualifier:
Acids / 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:
DK009970/DK/NIDDK NIH HHS; GM36044/GM/NIGMS NIH HHS; GM61406/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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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