Document Detail

Direct spectroscopic observation of binding of sugars to polymers having phenylboronic acids substituted with an ortho-phenylazo group.
MedLine Citation:
PMID:  20627667     Owner:  NLM     Status:  MEDLINE    
A novel vinyl monomer, 3-dimethylamino-6-(p-methacrylamidophenylazo)phenylboronic acid (AzoPBA), which had been prepared by the coupling of p-aminophenyl methacrylamide hydrochloride with m-dimethylaminophenylboronic acid in the presence of sodium nitrite, was polymerized with 3-dimethylaminopropylacrylamide (DMAPAA). The copolymer obtained (Poly(DMAPAA/AzoPBA)) bound to sugars such as fructose and glucose in a weakly alkaline region (8 < pH), which was indicated by the absorbance change of the diphenylazo group at 557 nm. In contrast with this, a copolymer of N,N-dimethylacrylamide (DMAA) and the AzoPBA (Poly(DMAA/AzoPBA)) bound to sugars in a more alkaline region (9 < pH). The larger sensitivity of the former copolymer to the sugars than the latter in a weakly alkaline region is due to the supporting effect of tertiary amino group in the DMAPAA residue to the binding of sugar to the phenylboronic acid moiety. The association constant (K) of boronic acid residue in these copolymers with fructose was larger than that with glucose. These results indicated the usefulness of the DMAPAA/AzoPBA copolymer for the sensing of sugars in the weakly alkaline region near the physiological pH.
Yu Okasaka; Hiromi Kitano
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Colloids and surfaces. B, Biointerfaces     Volume:  79     ISSN:  1873-4367     ISO Abbreviation:  Colloids Surf B Biointerfaces     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-07-16     Completed Date:  2010-10-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9315133     Medline TA:  Colloids Surf B Biointerfaces     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  434-9     Citation Subset:  IM    
Department of Applied Chemistry, Graduate School of Science and Engineering, University of Toyama, Gofuku 3190, Toyama 930-8555, Japan.
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MeSH Terms
Azo Compounds / chemistry,  metabolism*
Boronic Acids / chemistry*,  metabolism*
Carbohydrate Metabolism*
Ethylamines / metabolism
Hydrogen-Ion Concentration
Ovalbumin / metabolism
Polymers / metabolism*
Spectrophotometry, Ultraviolet
Reg. No./Substance:
0/Azo Compounds; 0/Boronic Acids; 0/Ethylamines; 0/Polymers; 0/Solutions; 121-44-8/triethylamine; 9006-59-1/Ovalbumin; 98-80-6/benzeneboronic acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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