| Linkage position analysis of pyridylamino-disaccharides by HPLC of fluorogenic Smith degradation products. | |
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MedLine Citation:
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PMID: 8056754 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Oligosaccharides are often converted to fluorogenic pyridylamino-oligosaccharides (PA-oligosaccharides) to be analyzed sensitively. A method for determining the glycosidic linkage position to the PA-reducing-end residue was developed with PA-disaccharides as model compounds. Periodate oxidation of PA-disaccharides was carried out at 0 degrees C for 15 min or at 4 degrees C for 40 h, and the reaction mixtures were reduced with borohydride. The fluorogenic products obtained at 4 degrees C for 40 h were purified by reversed phase HPLC, and the fraction collected were hydrolyzed with acid. The hydrolysates were analyzed by reversed phase HPLC. PA-glyceraldehyde was formed from 2-substituted PA-disaccharides with PA-hexose, PA-threose (or PA-erythrose) from 3-substituted ones, and PA-glycolaldehyde from 4- or 6-substituted ones. HPLC analysis of the products obtained at 0 degrees C for 15 min revealed a difference between 4- and 6-substituted ones. PA-glyceraldehyde was formed from 6-substituted ones, but not from 4-substituted ones. The linkage position, therefore, can be determined by analyzing fluorogenic product(s). As for PA-disaccharides with PA-N-acetylglucosamine, the linkage position can be simply determined by analysis of 40-h oxidation-reduction mixtures. 2-Acetamido-2-deoxy derivatives of PA-threose, PA-xylose, and PA-glyceraldehyde were formed from 3-, 4-, and 6-substituted ones, respectively. The linkage position analysis was successfully applied to determination of the structures of two Fuc-Man-PAs produced through the transglycosylation action of bovine kidney alpha-L-fucosidase. |
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Authors:
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K Omichi; S Hase |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of biochemistry Volume: 115 ISSN: 0021-924X ISO Abbreviation: J. Biochem. Publication Date: 1994 Mar |
Date Detail:
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Created Date: 1994-09-14 Completed Date: 1994-09-14 Revised Date: 2007-12-19 |
Medline Journal Info:
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Nlm Unique ID: 0376600 Medline TA: J Biochem Country: JAPAN |
Other Details:
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Languages: eng Pagination: 429-34 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Osaka University College of Science. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetylglucosamine
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chemistry Carbohydrate Conformation* Carbohydrate Sequence Chromatography, High Pressure Liquid* Disaccharides / chemistry* Glyceraldehyde / chemistry Hexoses / chemistry Molecular Sequence Data Oxidation-Reduction Periodic Acid |
| Chemical | |
Reg. No./Substance:
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0/Disaccharides; 0/Hexoses; 10450-60-9/Periodic Acid; 367-47-5/Glyceraldehyde; 7512-17-6/Acetylglucosamine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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