Document Detail

Linkage position analysis of pyridylamino-disaccharides by HPLC of fluorogenic Smith degradation products.
MedLine Citation:
PMID:  8056754     Owner:  NLM     Status:  MEDLINE    
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.
K Omichi; S Hase
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of biochemistry     Volume:  115     ISSN:  0021-924X     ISO Abbreviation:  J. Biochem.     Publication Date:  1994 Mar 
Date Detail:
Created Date:  1994-09-14     Completed Date:  1994-09-14     Revised Date:  2007-12-19    
Medline Journal Info:
Nlm Unique ID:  0376600     Medline TA:  J Biochem     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  429-34     Citation Subset:  IM    
Department of Chemistry, Osaka University College of Science.
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MeSH Terms
Acetylglucosamine / chemistry
Carbohydrate Conformation*
Carbohydrate Sequence
Chromatography, High Pressure Liquid*
Disaccharides / chemistry*
Glyceraldehyde / chemistry
Hexoses / chemistry
Molecular Sequence Data
Periodic Acid
Reg. No./Substance:
0/Disaccharides; 0/Hexoses; 10450-60-9/Periodic Acid; 367-47-5/Glyceraldehyde; 7512-17-6/Acetylglucosamine

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