@article{ni_kaur_springsteen_wang_franzen_2004, title={Regulating the fluorescence intensity of an anthracene boronic acid system: a B-N bond or a hydrolysis mechanism?}, volume={32}, ISSN={["1090-2120"]}, DOI={10.1016/j.bioorg.2004.06.004}, abstractNote={An anthracene-based fluorescent boronic acid system developed by the Shinkai group has been widely used for the preparation of fluorescent sensors for carbohydrates. Such application is based on the significant fluorescence intensity increase of this system upon binding with a carbohydrate. The mechanism through which this fluorescence intensity change happens was originally proposed to go through a B–N bond formation mechanism, which masks the nitrogen lone pair electrons. However, our own fluorescence studies suggest a possible alternative mechanism for the fluorescence change upon the formation of a boronic acid (1a) complex with diols. In this new proposed mechanism, complex formation induces solvolysis, which results in the protonation of the amine nitrogen if the reactions are carried out in a protic solvent such as water. This protonation prevents the photoinduced electron transfer, resulting in reduced quenching of the anthracene fluorescence. Such a solvolysis mechanism is supported by evidence from various types of experiments and theoretical calculations.}, number={6}, journal={BIOORGANIC CHEMISTRY}, author={Ni, WJ and Kaur, G and Springsteen, G and Wang, BH and Franzen, S}, year={2004}, month={Dec}, pages={571–581} }
 @article{ni_fang_springsteen_wang_2004, title={The design of boronic acid spectroscopic reporter compounds by taking advantage of the pK(a)-lowering effect of diol binding: Nitrophenol-based color reporters for diols}, volume={69}, ISSN={["1520-6904"]}, DOI={10.1021/jo0350357}, abstractNote={The complex that forms between a boronic acid and a diol is often much more acidic than the starting boronic acid. In conditions where the solution pH is between the two pK(a) values, the boron atom will convert from a neutral trigonal form to an anionic tetrahedral form upon complexation. Such a change is likely to dramatically alter the electron density of neighboring groups. Utilizing this effect, we have designed and synthesized two nitrophenol-based boronic acid reporter compounds that change ionization states and therefore spectroscopic properties upon diol binding. Both compounds show significant UV changes upon addition of saccharides. For example, a blue shift of the absorption max from 373 to 332 nm was observed with the addition of D-fructose to 2-hydroxy-5-nitrophenylboronic acid at neutral pH. Such a reporter compound can be used as a recognition and signaling unit for the construction of polyboronic acid sensors for the selective and specific recognitions of saccharides of biological significance.}, number={6}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Ni, WJ and Fang, H and Springsteen, G and Wang, BH}, year={2004}, month={Mar}, pages={1999–2007} }
 @article{yang_yan_springsteen_deeter_wang_2003, title={A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH}, volume={13}, ISSN={["1464-3405"]}, DOI={10.1016/S0960-894X(03)00086-6}, abstractNote={In this paper we report 8-quinolineboronic acid as a novel type of fluorescent probe for carbohydrates. This boronic acid responds to the binding of a carbohydrate with over 40-fold increases in fluorescence intensity and shows optimal fluorescence change at physiological pH in aqueous solution.}, number={6}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Yang, WQ and Yan, J and Springsteen, G and Deeter, S and Wang, BH}, year={2003}, month={Mar}, pages={1019–1022} }
 @article{springsteen_wang_2002, title={A detailed examination of boronic acid-diol complexation}, volume={58}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(02)00489-1}, abstractNote={Boronic acids bind with compounds containing diol moieties with high affinity through reversible boronate formation. However, the conditions that foster tight binding between the diol and the boronic acid are not well understood. Also, due to the multiple ionic states of both the boronic acid and boronate ester, the equilibrium constants reported in the literature have not always been strictly defined, and therefore there is a lack of ‘comparability’ between the reported values. To address these issues, we have developed a method for examining boronate ester stability using the fluorescent reporter Alizarin Red S. We have used this system to determine the binding constants of a series of diols, and as a basis from which to derive a number of relationships that correlate the various equilibrium constants in the literature.}, number={26}, journal={TETRAHEDRON}, author={Springsteen, G and Wang, BH}, year={2002}, month={Jun}, pages={5291–5300} }
 @article{yang_gao_springsteen_wang_2002, title={Catechol pendant polystyrene for solid-phase synthesis}, volume={43}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(02)01370-9}, abstractNote={A catechol pendant polystyrene polymer was prepared from the Merrifield resin via a convenient procedure with high-density loading. Due to the high affinity binding between catechol and boronic acid, the polymer resin readily captures boronic acid compounds. The feasibility of using immobilized catechol to capture boronic acid products for purification and solid-phase transformation was demonstrated. Moreover, the immobilized catechol was also used for the preparation of resin-bound catecholborane, which can be used as a solid-phase amidation reagent.}, number={36}, journal={TETRAHEDRON LETTERS}, author={Yang, WQ and Gao, XM and Springsteen, G and Wang, BH}, year={2002}, month={Sep}, pages={6339–6342} }
 @article{springsteen_wang_2001, title={Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates}, number={17}, journal={Chemical Communications (Cambridge, England)}, author={Springsteen, G. and Wang, B. H.}, year={2001}, pages={1608–1609} }
 @article{latta_springsteen_wang_2001, title={Development and synthesis of an arylboronic acid-based solid-phase amidation catalyst}, number={11}, journal={Synthesis (Stuttgart)}, author={Latta, R. and Springsteen, G. and Wang, B. H.}, year={2001}, pages={1611–1613} }
 @article{springsteen_ballard_gao_wang_wang_2001, title={The development of photometric sensors for boronic acids}, volume={29}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.2001.1217}, abstractNote={Boronic acids bind certain 1,2- and 1,3-diols with high affinity through reversible formation of boronate esters. They have been utilized as the recognition moiety for artificial receptors, particularly receptors for carbohydrates that have cis-diol moieties. Therefore, sensors for boronic acids could serve as universal reporters for monitoring boronate formation. This paper reports the design and synthesis of a series of photometric chemosensors for phenylboronic acid using diethanolamine as the recognition moiety. Diethanolamine, which binds strongly to boronic acids, has been linked to three different types of optical reporters. A photoinduced electron transfer system based on the anthracene fluorophore has been used to create sensors that show up to a fivefold increase in fluorescent intensity in the presence of millimolar concentrations of phenylboronic acid. Sensor designs based on the restriction of free rotation of extended pi systems and on the perturbed electronic properties of azo dyes are also included. This work demonstrates that sensors based on several different designs can be used for the detection of boronic acids.}, number={5}, journal={BIOORGANIC CHEMISTRY}, author={Springsteen, G and Ballard, CE and Gao, S and Wang, W and Wang, BH}, year={2001}, month={Oct}, pages={259–270} }
 @article{wang_springsteen_gao_wang_2000, title={The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations}, number={14}, journal={Chemical Communications (Cambridge, England)}, author={Wang, W. and Springsteen, G. and Gao, S. H. and Wang, B. H.}, year={2000}, pages={1283–1284} }