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Chemical Compound Review:

zlchem 430 (3-aminophenyl)boronic acid

Synonyms: CHEMBL20852, SureCN22913, ACMC-1CTTO, AG-E-89696, AG-F-00216, ...

Cruschelli, L. et al., Peaston, R.T., Usher, K.C. et al., Yue, D.K. et al., Stockham, T.L. et al., et al.

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Disease relevance of M-AMINOPHENYLBORONIC ACID

Evidence of a role for NAD+-glycohydrolase and ADP-ribosyltransferase in growth and differentiation of Streptomyces griseus NRRL B-2682: inhibition by m-aminophenylboronic acid [1].

High impact information on M-AMINOPHENYLBORONIC ACID

Tritiated glycosylated amino acids could be selectively removed by m-aminophenylboronic acid immobilized on Biogel P-6, then eluted by acidification and the radioactivity in the acidic peak used to estimate non-enzymatic glycosylation [2].
The structure of the m-aminophenylboronic acid adduct also suggests several ways to improve the affinity of this class of inhibitor and points to the existence of several unusual binding-site-like features in the region of the AmpC catalytic site [3].
This study describes the attempt to isolate and purify an acetaldehyde-hemoglobin adduct in alcoholics by cation-exchange chromatography and m-aminophenylboronic acid affinity chromatography for the purpose of characterization [4].

Analytical, diagnostic and therapeutic context of M-AMINOPHENYLBORONIC ACID

The catecholamines are isolated from urine samples using small affinity chromatography columns prepacked with immobilised m-aminophenylboronic acid, separated by ion-pair reversed-phase liquid chromatography and quantified by electrochemical detection [5].
We have developed a boronate affinity immunoassay system using m-aminophenylboronic acid (mAPB) coupling to bacterial magnetic particles (BMPs) [6].
When [14C]glycated-HSA purified by Sephadex G25 filtration was chromatographed using the m-aminophenylboronic acid, only 5.3% of the total 14C-radioactivity present in the solution was recovered in the bound fraction, while 44.0% was eluted in non-protein-bound fraction and 54.7% was retained in the column [7].

References

Evidence of a role for NAD+-glycohydrolase and ADP-ribosyltransferase in growth and differentiation of Streptomyces griseus NRRL B-2682: inhibition by m-aminophenylboronic acid. Penyige, A., Deák, E., Kálmánczhelyi, A., Barabás, G. Microbiology (Reading, Engl.) (1996) [Pubmed]
Non-enzymatic glycosylation of tissue protein in diabetes in the rat. Yue, D.K., McLennan, S., Turtle, J.R. Diabetologia (1983) [Pubmed]
Three-dimensional structure of AmpC beta-lactamase from Escherichia coli bound to a transition-state analogue: possible implications for the oxyanion hypothesis and for inhibitor design. Usher, K.C., Blaszczak, L.C., Weston, G.S., Shoichet, B.K., Remington, S.J. Biochemistry (1998) [Pubmed]
Investigation of an acetaldehyde-hemoglobin adduct in alcoholics. Stockham, T.L., Blanke, R.V. Alcohol. Clin. Exp. Res. (1988) [Pubmed]
Routine determination of urinary free catecholamines by high-performance liquid chromatography with electrochemical detection. Peaston, R.T. J. Chromatogr. (1988) [Pubmed]
Detection of HbA(1c) by boronate affinity immunoassay using bacterial magnetic particles. Tanaka, T., Matsunaga, T. Biosensors & bioelectronics. (2001) [Pubmed]
Colorimetric versus radioimmunological measurement of glycated and non-glycated serum albumin after affinity chromatography. Cruschelli, L., Clerico, A., Penno, G., Navalesi, R., Giampietro, O. Acta diabetologica latina. (1990) [Pubmed]

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