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Chemical Compound Review

PubChem1753     phenylboronic acid

Synonyms: SureCN4453, CHEMBL21485, ARONIS010113, P20009_ALDRICH, AG-I-00382, ...
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Disease relevance of phenylboronic acid


High impact information on phenylboronic acid


Biological context of phenylboronic acid

  • A highly rigid dibenzo[a,d]cycloheptenyl dibenzophosphole with a pre-organized concave shaped binding site acts as an efficient ligand in the palladium catalyzed Suzuki-Miyaura coupling process between halogenoaromatics and phenylboronic acid [9].
  • [reaction: see text] A phenylboronic acid derivative of a well-known dye (Lucifer yellow) recognizes L-DOPA through a combination of reversible esterification, charge transfer, and electrostatic interactions [10].
  • Among the three phenylboronic acid derivatives, i.e. 4-(4, 5-diphenyl-1H-imidazol-2-yl)phenylboronic acid (DPA), 4-[4(or 5)-(4-dimethylaminophenyl)-5(or 4)-phenyl-1H-imidazol-2-yl]phenylboronic acid (DAPA) and 4-[4, 5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid (DPPA), DPPA was found to be the most potent enhancer [11].
  • A phenylboronic acid (PBA) derivatized Bond Elut column has been investigated for the selective purification of oligosaccharide alditols and of oligosaccharide derivatives formed by reductive amination reactions [12].
  • The kinetics of inhibition of rice bran lipase (RBL) by phenylboronic acid (PBA) was studied to elucidate the nature of inhibition and the effect of the inhibitor on the structure-function of RBL [13].

Anatomical context of phenylboronic acid


Associations of phenylboronic acid with other chemical compounds


Gene context of phenylboronic acid

  • Excellent hCA IV inhibitory properties showed sulfamic acid, sulfamide, phenylboronic acid and phenylarsonic acid, with K(i)'s in the range of 0.87-0.93 microM, whereas their affinities for the other investigated isozymes were in the millimolar range [21].
  • The urine was treated with beta-glucuronidase and sulfatase, and then the BaP-tetraols were enriched by reverse-phase and phenylboronic acid solid-phase extraction [22].
  • The monomeric diphosphino Pd(II) complex 1 and the first three generations of dendritic analogues G1, G2, and G3 are efficient catalysts for the Suzuki coupling reaction of halogenoarenes, including chloroarenes with phenylboronic acid [23].
  • [reaction: see text] Cyclopalladated compounds derived from the ortho-metalation of benzylic tert-butyl thioethers are excellent catalyst precursors for the Suzuki cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under mild reaction conditions [24].
  • Lectin-like function was demonstrated in this study for a novel water-soluble polymer with phenylboronic acid residues (poly (AAPBA-DMAm)), which induced appreciable proliferation of murine spleen lymphocytes with an increased expression of interleukin-2 (IL-2) receptor on their surface [25].

Analytical, diagnostic and therapeutic context of phenylboronic acid


  1. Beta-lactamase inhibitors. The inhibition of serine beta-lactamases by specific boronic acids. Crompton, I.E., Cuthbert, B.K., Lowe, G., Waley, S.G. Biochem. J. (1988) [Pubmed]
  2. Phenylboronic acid as a ligand for biospecific chromatography of serine proteinases. Akparov, V.K., Stepanov, V.M. J. Chromatogr. (1978) [Pubmed]
  3. Synthesis and in vitro evaluation of the phenylboric acid derivative entrapped lipiodol in boron neutron capture therapy for hepatoma. Chou, F.I., Chung, H.P., Shieh, M.S., Huang, C.W., Chung, R.J., Liu, H.M., Yang, J.Y., Chi, C.W., Lin, Y.C., Lui, W.Y., Kai, J.J. Anticancer Res. (2003) [Pubmed]
  4. p-Nitrophenyl and cholesteryl-N-alkyl carbamates as inhibitors of cholesterol esterase. Hosie, L., Sutton, L.D., Quinn, D.M. J. Biol. Chem. (1987) [Pubmed]
  5. Molecular recognition of sialic acid end groups by phenylboronates. Djanashvili, K., Frullano, L., Peters, J.A. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  6. Affinity interactions between phenylboronic acid-carrying self-assembled monolayers and flavin adenine dinucleotide or horseradish peroxidase. Liu, S., Wollenberger, U., Halámek, J., Leupold, E., Stöcklein, W., Warsinke, A., Scheller, F.W. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  7. Purification and structure-function analysis of native, PNGase F-treated, and endo-beta-galactosidase-treated CHIP28 water channels. van Hoek, A.N., Wiener, M.C., Verbavatz, J.M., Brown, D., Lipniunas, P.H., Townsend, R.R., Verkman, A.S. Biochemistry (1995) [Pubmed]
  8. Proton nuclear magnetic resonance evidence for the absence of a stable hydrogen bond between the active site aspartate and histidine residues of native subtilisins and for its presence in thiolsubtilisins. Jordan, F., Polgár, L. Biochemistry (1981) [Pubmed]
  9. Dibenzo[a,d]cycloheptenyl dibenzophosphole palladium dichloride: synthesis, X-ray-crystal structure and application in the Suzuki-Miyaura coupling. Thoumazet, C., Ricard, L., Grützmacher, H., Le Floch, P. Chem. Commun. (Camb.) (2005) [Pubmed]
  10. Three-point recognition and selective fluorescence sensing of L-DOPA. Coskun, A., Akkaya, E.U. Org. Lett. (2004) [Pubmed]
  11. New phenylboronic acid derivatives as enhancers of the luminol-H(2)O(2)-horseradish peroxidase chemiluminescence reaction. Kuroda, N., Kawazoe, K., Nakano, H., Wada, M., Nakashima, K. Luminescence : the journal of biological and chemical luminescence. (1999) [Pubmed]
  12. Selective purification of reduced oligosaccharides using a phenylboronic acid bond elut column: potential application in HPLC, mass spectrometry, reductive amination procedures and antigenic/serum analysis. Stoll, M.S., Hounsell, E.F. Biomed. Chromatogr. (1988) [Pubmed]
  13. Phenylboronic acid--a potent inhibitor of lipase from Oryza sativa. Raghavendra, M.P., Prakash, V. J. Agric. Food Chem. (2002) [Pubmed]
  14. Boronate-containing polymer as novel mitogen for lymphocytes. Miyazaki, H., Kikuchi, A., Koyama, Y., Okano, T., Sakurai, Y., Kataoka, K. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  15. Effect of phenylboronic acid groups in copolymers on endothelial cell differentiation into capillary structures. Aoki, T., Nagao, Y., Sanui, K., Ogata, N., Kikuchi, A., Sakurai, Y., Kataoka, K., Okano, T. Journal of biomaterials science. Polymer edition. (1997) [Pubmed]
  16. Phenylboronic acid-salicylhydroxamic acid bioconjugates. 1. A novel boronic acid complex for protein immobilization. Stolowitz, M.L., Ahlem, C., Hughes, K.A., Kaiser, R.J., Kesicki, E.A., Li, G., Lund, K.P., Torkelson, S.M., Wiley, J.P. Bioconjug. Chem. (2001) [Pubmed]
  17. Colloidal gold nanoparticles as catalyst for carbon-carbon bond formation: application to aerobic homocoupling of phenylboronic acid in water. Tsunoyama, H., Sakurai, H., Ichikuni, N., Negishi, Y., Tsukuda, T. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  18. New derivatives for the analysis of sphingosine long-chain bases by gas-liquid chromatography-mass spectrometry. Gaskell, S.J., Brooks, C.J. J. Chromatogr. (1976) [Pubmed]
  19. Glucose-sensitive inverse opal hydrogels: analysis of optical diffraction response. Lee, Y.J., Pruzinsky, S.A., Braun, P.V. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  20. Amine effect on phenylboronic acid complex with glucose under physiological pH in aqueous solution. Shiino, D., Kubo, A., Murata, Y., Koyama, Y., Kataoka, K., Kikuchi, A., Sakurai, Y., Okano, T. Journal of biomaterials science. Polymer edition. (1996) [Pubmed]
  21. Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Innocenti, A., Firnges, M.A., Antel, J., Wurl, M., Scozzafava, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  22. Determination of r-7,t-8,9,c-10-tetrahydroxy-7,8,9, 10-tetrahydrobenzo[a]pyrene in human urine by gas chromatography/negative ion chemical ionization/mass spectrometry. Simpson, C.D., Wu, M.T., Christiani, D.C., Santella, R.M., Carmella, S.G., Hecht, S.S. Chem. Res. Toxicol. (2000) [Pubmed]
  23. Efficient dendritic diphosphino Pd(II) catalysts for the Suzuki reaction of chloroarenes. Lemo, J., Heuzé, K., Astruc, D. Org. Lett. (2005) [Pubmed]
  24. Sulfur-containing palladacycles: efficient phosphine-free catalyst precursors for the Suzuki cross-coupling reaction at room temperature. Zim, D., Gruber, A.S., Ebeling, G., Dupont, J., Monteiro, A.L. Org. Lett. (2000) [Pubmed]
  25. Totally synthetic polymer with lectin-like function: induction of killer cells by the copolymer of 3-acrylamidophenylboronic acid with N,N-dimethylacrylamide. Uchimura, E., Otsuka, H., Okano, T., Sakurai, Y., Kataoka, K. Biotechnol. Bioeng. (2001) [Pubmed]
  26. Separation of glycosylated haemoglobins using immobilized phenylboronic acid. Effect of ligand concentration, column operating conditions, and comparison with ion-exchange and isoelectric-focusing. Middle, F.A., Bannister, A., Bellingham, A.J., Dean, P.D. Biochem. J. (1983) [Pubmed]
  27. Determination of 6-keto-PGF1 alpha, 2,3-dinor-6-keto-PGF1 alpha, thromboxane B2, 2,3-dinor-thromboxane B2, PGE2, PGD2 and PGF2 alpha in human urine by gas chromatography-negative ion chemical ionization mass spectrometry. Weber, C., Höller, M., Beetens, J., De Clerck, F., Tegtmeier, F. J. Chromatogr. (1991) [Pubmed]
  28. Selective extraction of beta-blockers from biological fluids by column-switching high-performance liquid chromatography using an internal-surface phenylboronic acid precolumn. Ohta, T., Niida, S., Nakamura, H. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
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