Welcome to The Tzu-Pin Wang Group

My research group has been focused on four major research areas: 1) nucleic acid modifications for biomolecule detection and quantification, and nucleic acid therapeutics development, 2) discovery of novel RNA catalysts and aptamers, 3) organic synthesis of fluorescence chemical probes for quantification of enzyme activity and early detection of diseases in human, and 4) agarose chemistry for development of agarose-based biomaterials useful in biotechnology.

 

Research Highlights

    1. Nucleic acid chemistry and applications: Topics include phosphoramidation chemistry for post-synthetic modifications and conjugations of DNA/RNA; novel and effective bioorthogonal chemical approaches for nucleic acid modifications and labeling; novel approaches for synthesis of peptide-oligonucleotide conjugates (POCs); synthesis of POCs for achieving gene silencing and RNA interference ; novel methods for universal labeling and modifications DNA/RNA; phosphoramidation reactions for DNA microarray fabrication and detection; novel ribozymes and aptamers for developments of nucleic acid-based biosensors.
    2. Chemistry of ribozymes and aptamers: Topics include in vitro evolution and selection of novel ribozymes and aptamers; structure determination of ribozymes and aptamers; determination of catalytical mechanisms of ribozymes.
    3. Bioorthogonal chemistry-based syntheses of fluorescence chemical probes and their applications: Topics include organic synthesis of fluorescence chemical probes, quantification of enzyme activity by changes in fluorescence, and in situ and in vivo detection of redox and biothiol homeostasis changes in biological sysytems.
    4. Agarose Chemistry: Topics include purification of biotechnological grade agarose from indigenous Rhodophyta in Taiwan; synthesis of agarose derivatives useful in biotechnology and bioengineering.

 

Publications since 2010

Huang, C.-H., S.-Y. Hou, S. Severance, C.-C. Hwang, B.-K. Fang, M.-M. Gong, S.-L. Yu, Y.-C. Weng, L.-F. Wang, C.-Y. Dai, S.-H. Wang, H.-T. Kuo, J.-J. Wang, and T.-P. Wang* (2023) Manipulating diastereomeric bicyclononynes to sensitively determine enzyme activity and facilitate macromolecule conjugations. ACS Omega, 8 (48), 46073−46090. http://doi.org/10.1021/acsomega.3c07083.

Chou, Y.-H., C.-L. Hsieh, Y.-L. Chen, T.-P. Wang, W.-J. Wu, C.-C. Hwang* (2023) Characterization of the pH-dependent protein stability of 3α-hydroxysteroid dehydrogenase/carbonyl reductase by differential scanning fluorimetry. Protein Sci., 32 (8), e4710. https://doi.org/10.1002/pro.4710

Chen,Y.-L., Y.-H. Chou, C.-L. Hsieh, S.-J. Chiou, T.-P. Wang and Chi-Ching Hwang*. (2022) Rational Engineering of 3a-hydroxysteroid dehydrogenase/carbonyl reductase for a biomimetic nicotinamide mononucleotide cofactor. Catalysts, 12 (10), 1094. doi: 10.3390/catal12101094.

Huang, C.-H., Y.-T. Chang, S. Severance, J.-Y. Feng S.-Y. Hou, M.-M. Gong, C.-C. Hwang, C.‐Y. Dai, J.-J. Wang and T.-P. Wang*. (2022) Time-dependent effects of storage at –80 °C on the stability of butyrylcholinesterase activity in human serum. Pract. Lab. Med., 31, e00298. https://www.sciencedirect.com/science/article/pii/S2352551722000373

Fang, B.-K., C.-Y. Dai, S. Severance, C.-C. Hwang, C.-H. Huang, S.-Y. Hou, B.-L. Yeh, M.-M. Gong , Y.-H. Chou, J.-J. Wang and T.-P. Wang*. (2022) Sensitive assay for the lactonase activity of serum paraoxonase 1 (PON1) by harnessing the fluorescence turn-on characteristics of bioorthogonally synthesized and geometrically controlled chemical probes. Molecules, 27 (8), 2435. https://www.mdpi.com/1420-3049/27/8/2435/htm

Gong, M.-M., C.-Y. Dai, S. Severance, C.-C. Hwang, B.-K. Fang, H.-B. Lin, C.-H. Huang, C.-W. Ong, J.-J. Wang, P.-L. Lee and T.-P. Wang*. (2020) Bioorthogonally synthesized and disulfide-containing fluorescence turn-on chemical probe for measurements of butyrylcholinesterase activity and inhibition in the presence of physiological glutathione. Catalysts, 10 (10), 1169; doi:10.3390/catal10101169

Hwang, C.-C.,* P.-R. Chang, C.-L. Hsieh, Y.-H. Chou, T.-P. Wang. (2019) Thermodynamic analysis of remote substrate binding energy in 3α-hydroxysteroid dehydrogenase/carbonyl reductase catalysis. Chem. Biol. Interact., 302, 183-189.

Wang, T.-P. *, Y.-C. Su, Y. Chen, S. Severance, C.-C. Hwang, Y.-M. Liou, C.-H. Lu, K.-L. Lin, R. J. Zhu, E.-C. Wang. (2018) Corroboration of Zn(II)-Mg(II)-tertiary structure interplays essential to optimal catalysis of a phosphorothiolate thiolesterase ribozyme. RSC Adv., 8, 32775-32793. https://pubs.rsc.org/en/content/articlepdf/2018/ra/c8ra05083j

Hwang, C.-C.*, P.-R. Chang, T.-P. Wang. (2017) Contribution of remote substrate binding energy to the enzymatic rate acceleration for 3α-hydroxysteroid dehydrogenase/carbonyl reductase. Chem. Biol. Interact. , 276, 133-140.

Su, Y.-C., Y.-L. Lo, C.-C. Hwang, L.-F. Wang, M. H. Wu, E.-C. Wang, Y.-M. Wang, T.-P. Wang*. (2014) Azide–alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates. Org. Biomol. Chem., 12, 6624–6633.

Su, Y.-C., H.-Y. Chen, N. C. Ko, C.-C. Hwang, M. H. Wu, L.-F. Wang, Y.-M. Wang, S.-N. Chang, E.-C. Wang*, T.-P. Wang*. (2014) Effective and site-specific phosphoramidation reaction for universally labeling nucleic acids. Anal. Biochem., 449, 118-128.

Chang, Y.-T., C.-Y. Lin, P.-L. Lu, C.-C. Lai, T.-C. Chen, C.-Y. Chen, D.-C. W, T.-P. Wang, C.-M. Lin, W.-R. Lin*, Y.-H. Chen. (2014) Stenotrophomonas maltophilia bloodstream infection: Comparison between community-onset and hospital-acquired infections. J. Microbiol. Immunol. Infect., 47, 28-35.

Huang, S.-J., T.-P. Wang, S.-I. Lue, L.-F. Wang*. (2013) Pentablock copolymers of pluronic F127 and modified poly(2-dimethyl amino)ethyl methacrylate for internalization mechanism and gene transfection studies. Int. J. Nanomedicine, 8, 2011–2027.

Hwang, C.-C.*, Y.-H. Chang, H.-J. Lee, T.-P. Wang, Y.-M. Su, H.-W. Chen, P.-H. Liang. (2013) The Catalytic Roles of P185 and T188 and Substrate-Binding Loop Flexibility in 3a-Hydroxysteroid Dehydrogenase/Carbonyl Reductase from Comamonas testosterone. PLOS ONE. 8, e63594.

Wu, S.-C., K.-L. Lin, T.-P. Wang, S.-C. Tzou, G. Singh, M.-H. Chen, T.-L. Cheng, C.-Y. Chen, G.-C. Liu, T.-W. Lee, S.-H. Hu, and Y.-M. Wang*. (2013) Imaging specificity of MR-optical imaging agents following the masking of surface charge by poly(ethylene glycol). Biomaterials, 34, 4118-4127.

Hsu, S. C. N., T.-P. Wang, C.-L. Kao, H.-F. Chen, P.-Y. Yang, and H.-Y. Chen*. (2013) Theoretical study on the protonation of the one-electron reduced guanine-cytosine base pair by water. J. Phys. Chem. B, 117, 2096−2105.

Chen, P.-Y., C.-Y. Zhou, H.-M. Chen, C.-H. Yang, T.-P. Wang*, and E.-C. Wang*. (2013) Synthesis of novel four-fused-ring chromeno-benzoxepinones from salicylaldehydes and 1-benzoxepin-5-ones via the oxa-Michael reaction/aldol condensation. ARKIVOC, (iii) 24-35.

Chen, P.-Y., Y.-H. Wu, M.-H. Hsu, T.-P. Wang, E.-C. Wang*. (2013) Cerium ammonium nitrate-mediated the oxidative dimerization of p-alkenylphenols: a new synthesis of substituted (±)-trans-dihydrobenzofurans. Tetrahedron, 69. 653-657

Wang, T.-P.*, N. C. Ko, Y.-C. Su, E.-C. Wang, S. Severance, C.-C. Hwang, Y. T. Shih, M. H. Wu and Y.-H. Chen*. (2012) Advanced aqueous-phase phosphoramidation reactions for effectively synthesizing peptide-oligonucleotide conjugates trafficked into a human cell line. Bioconjugate Chem., 23, 2417-2433.

Chen,S.-H., Y.-T. Kuo, G. Singh, T.-L. Cheng, Y.-Z. Su, T.-P. Wang, Y.-Y. Chiu, J.-J. Lai, C.-C. Chang, T.-S. Jaw, S.-C. Tzou, G.-C. Liu*, and Y.-M. Wang*. (2012) Development of a Gd(III) Based Receptor-Induced Magnetization Enhancement (RIME) Contrast Agent for b-Glucuronidase Activity Profiling. Inorg. Chem., 51, 12426-12435.

Chen, P.-Y., K.-S. Huang, C.-C. Tsai, T.-P. Wang, and E.-C. Wang*. (2012) Pd(II)-Mediated Cyclization of o-Allylbenzaldehydes in Water: A Novel Synthesis of Isocoumarins. Org. Lett., 14, 4930-4933.

Chen, P.-Y., H.-M. Chen, M. Y. Chiang, Y.-F. Wang, S-R. Li, T.-P. Wang, E.-C. Wang*. (2012) A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN. Tetrahedron, 68, 3030-3036.

Wang, T.-P.*, L.-L. Chang, S.-N. Chang, E.-C. Wang, L.-C. Hwang, Y.-H. Chen, and Y.-M. Wang (2012) Successful Preparation and Characterization of Biotechnological Grade Agarose from Indigenous Gelidium amansii of Taiwan. Process Biochem., 47, 550–554.

Wang, T.-P.*, Y.-C. Su, Y. Chen, Y.-M. Liou, K.-L. Lin, E.-C. Wang, L.-C. Hwang, Y.-M. Wang, and Y.-H. Chen (2012) In vitro Selection and Characterization of a Novel Zn(II)-Dependent Phosphorothiolate Thiolesterase Ribozyme. Biochemistry, 51, 496-510.

Chen, B.-H.*, M.-H. Hung, J. Y.-F. Chen, H.-W. Chang, M.-L. Yu, L. Wan, F. J. Tsai, T.-P. Wang, T.-F. Fu, C.-C. Chiu (2012) Anti-allergic activity of grapeseed extract (GSE) on RBL-2H3 mast cells. Food Chem., 132, 968-974.

Chen, P.-Y., T.-P. Wang, K.-S. Huang, C.-L. Kao, J.-C. Tsai, E.-C. Wang* (2011) tert-BuOK-mediated carbanioneyne intramolecular cyclization: synthesis of 2-substituted 3-benzylbenzofurans. Tetrahedron, 67, 9291-9297.

Chen, P.-Y., T.-P. Wang, M. Y. Chiang, K.-S. Huang, C.-C. Tzeng, Y.-L. Chen, E.-C. Wang*. (2011) Environmentally benign syntheses of flavanones. Tetrahedron, 67, 4155-4160.

Chen, L.-Y., S.-R. Li, P.-Y. Chen, H.-C. Chang, T.-P. Wang, I.-L. Tsai, and E.-C. Wang*. (2010) 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) mediated oxidation-dehydrogenation of 2-aroyl-3,4-dihydro-2H-benzopyrans : synthesis of 2-aroylbenzopyran-4-ones. ARKIVO, xi, 64-76.

Hwang, L.-C.*, Y.-C. Su, T.-P. Wang, L.-T. Liu, and G.-H. Lee (2010) Crystal structure of 3-amino-2-benzyl-6-bromo-1,2,4-triazin-5(2H)-one. X-ray Struct. Anal. Online, 26, 61-62.

Ko, C.-H.*, Z.-P. Lin, J. Tu, C.-H. Tsai, C.-C. Liu, H.-T. Chen, T.-P. Wang (2010) Xylanase production by Paenibacillus campinasensis BL11 and its pretreatment of hardwood kraft pulp bleaching.  Int. Biodeterior. Biodegradation., 64, 13–19.

Su, S.-H., W.-C. Tsai, C.-Y. Lin, W.-R. Lin, T.-C. Chen, P.-L. Lu, P.-M. Huang, J.-R. Tsai, Y.-L. Wang, M.-C. Feng, T.-P. Wang, Y.-H. Chen (2010) Clinical features and outcomes of spinal tuberculosis in southern Taiwan.  J. Microbiol. Immunol. Infect., 43, 291–300.

Wang, T.-P.*, Y.-J. Chiou, Y. Chen, E.-C. Wang, L.-C. Hwang, B.-H. Chen, Y.-H. Chen, and C.-H. Ko (2010) Versatile phosphoramidation reactions for nucleic acid conjugations with peptides, proteins, chromophores, and biotin derivatives. Bioconjugate Chem. 21, 1642–1655.

 

Patents

Wang, T.-P., C.-Y. Dai, B.-K. Fang, and C.-H. Huang (2023) 雙環壬炔衍生物及其製備方法和用途(Bicyclononyne derivatives and manufacturing method and use thereof), Taiwan Patent No.: I818431, Date of Patent: Oct 11, 2023.

Wang, T.-P. and Y.-C. Su (2018) Reagents for universal site-specific labeling and modifications of nucleic acids, U.S. Patent No.: US 9,856,285 B2, Date of Patent: Jan. 02, 2018.

Wang, T.-P. N. C. Ko, and Y.-C. Su (2015)核酸共軛物的液相合成法(Liquid phase synthesis of a nucleic acid conjugate), Taiwan Patent No.: I471331, Date of Patent: Feb. 1, 2015.

Wang, T.-P. and Y.-J. Chiou (2014) Methods for conjugating nucleic acids with small molecules, U.S. Patent No.: US 8,765,934 B2, Date of Patent: Jul. 1, 2014.

Wang, T.-P. and Y.-J. Chiou (2014)將核酸街上小分子的方法(Methods for conjugating nucleic acids with small molecules), Taiwan Patent No.: I464402, Date of Patent: Dec. 11, 2014.

 

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