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Dr James Redman
Senior Lecturer in Chemical Biology
- Media commentator
Overview
Dr Redman's research interests are in the areas of amino acid, protein and peptide chemistry, nucleic acids and mass spectrometry.
This work involves the synthesis of amino acids with heterocyclic side chains designed as building blocks for nucleic acid-binding peptides. We are preparing amino acids with mono- and bicyclic guanidine side chains as constrained analogues of arginine that are predicted to form hydrogen bonded interactions with nucleobases. Peptides can also be constrained by backbone cyclisation and we are investigating the use of computer aided interpretation of collision induced dissociation mass spectra of cyclic peptides as a tool for characterisation of this class of compound. A further project involves using phage display techniques to select allosteric DNA binding proteins, with the goal of creating artificial transcription factors that can be switched using a small molecule drug.
Links
Personal Web Site: James Redman
Publication
2024
- Alaboosh, J. M. H., Hill, S. P., Kariuki, B. M. and Redman, J. E. 2024. Crystal structures of sulfonamide protected bicyclic guanidines: (S)-8-{[(tert-butyldimethylsilyl)oxy]methyl}-1-[(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl]-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidin-1-ium trifluoromethanesulfonate and (S)-8-(iodomethyl)-1-tosyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidin-1-ium iodide. Acta Crystallographica Section E: Crystallographic Communications 80(3), pp. 305-309. (10.1107/S2056989024001129)
2023
- Smith, D. A., Redman, J. E., Fraser, D. J. and Bowen, T. 2023. Identification and detection of microRNA kidney disease biomarkers in liquid biopsies. Current Opinion in Nephrology and Hypertension 32(6), pp. 515-521. (10.1097/MNH.0000000000000927)
- Shepherd, F. R. et al. 2023. The superantigens SpeC and TSST-1 specifically activate TRBV12-3/12-4+ memory T cells. Communications Biology 6, article number: 78. (10.1038/s42003-023-04420-1)
2021
- Exner, R. M., Paisey, S. J., Redman, J. E. and Pascu, S. I. 2021. Explorations into peptide nucleic acid contrast agents as emerging scaffolds for breakthrough solutions in medical imaging and diagnosis. ACS Omega 6(43), pp. 28455-28462. (10.1021/acsomega.1c03994)
- Man, S. et al. 2021. Synthetic peptides with inadvertent chemical modifications can activate potentially autoreactive T cells. The Journal of Immunology 207(4), pp. 1009-1017. (10.4049/jimmunol.2000756)
- Smith, D. A. et al. 2021. Detection of urinary microRNA biomarkers using diazo sulfonamide-modified screen printed carbon electrodes. RSC Advances 11(31), pp. 18832-18839. (10.1039/D0RA09874D)
2017
- Smith, D., Newbury, L., Drago, G., Bowen, T. and Redman, J. E. 2017. Electrochemical detection of urinary microRNAs via sulfonamide-bound antisense hybridisation. Sensors and Actuators B: Chemical 253, pp. 335-341. (10.1016/j.snb.2017.06.069)
2015
- Reid, R., Redman, J. E., Rizkallah, P., Fegan, C. D., Pepper, C. J. and Man, S. T. 2015. CD8+ T-cell recognition of a synthetic epitope formed by t-butyl modification. Immunology 144(3), pp. 495-505. (10.1111/imm.12398)
2013
- Möschwitzer, V. D., Kariuki, B. and Redman, J. E. 2013. Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids. Tetrahedron Letters 54(34), pp. 4526-4528. (10.1016/j.tetlet.2013.06.066)
2011
- Michael, D. R. et al. 2011. The human hyaluronan synthase 2 (HAS2) gene and its natural antisense RNA exhibit coordinated expression in the renal proximal tubular epithelial cell. Journal of Biological Chemistry 286(22), pp. 19523-19532. (10.1074/jbc.M111.233916)
- Rouziere, A. and Redman, J. E. 2011. A practical workshop for generating simple DNA fingerprints of plants. Biochemistry and Molecular Biology Education 39(3), pp. 204-210. (10.1002/bmb.20486)
2010
- Jenkins, R. H., Bennagi, R., Martin, J., Phillips, A. O., Redman, J. E. and Fraser, D. J. 2010. A conserved stem loop motif in the 5'Untranslated Region regulates transforming growth factor-β1 translation. PLoS One 5(8), article number: e12283. (10.1371/journal.pone.0012283)
2009
- Redman, J. E., Granadino-Roldán, J. M., Schouten, J. A., Ladame, S., Reszka, A. P., Neidle, S. and Balasubramanian, S. 2009. Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates. Organic & Biomolecular Chemistry 7(1), pp. 76-84. (10.1039/b814682a)
2007
- Redman, J. E. 2007. Surface plasmon resonance for probing quadruplex folding and interactions with proteins and small molecules. Methods 43(4), pp. 302-312. (10.1016/j.ymeth.2007.05.008)
2006
- Ladame, S., Schouten, J. A., Roldan, J., Redman, J. E., Neidle, S. and Balasubramanian, S. 2006. Exploring the Recognition of Quadruplex DNA by an Engineered Cys2-His2 Zinc Finger Protein. Biochemistry 45(5), pp. 1393-1399. (10.1021/bi050229x)
2005
- Yadav, M. K., Redman, J. E., Leman, L. J., Alvarez-Gutiérrez, J. M., Zhang, Y., Stout, C. D. and Ghadiri, M. R. 2005. Structure-Based Engineering of Internal Cavities in Coiled-Coil Peptides. Biochemistry 44(28), pp. 9723-9732. (10.1021/bi050742a)
2002
- Redman, J. E., Wilcoxen, K. M. and Ghadiri, M. R. 2002. Automated mass spectrometric sequence determination of cyclic peptide library members. Journal of Combinatorial Chemistry 5(1), pp. 33-40. (10.1021/cc0200639)
2001
- Cousins, G. R. L., Furlan, R. L. E., Ng, Y., Redman, J. E. and Sanders, J. K. M. 2001. Identification and Isolation of a Receptor for N-Methyl Alkylammonium Salts: Molecular Amplification in a Pseudo-peptide Dynamic Combinatorial Library. Angewandte Chemie International Edition 40(2), pp. 423-428. (10.1002/1521-3773(20010119)40:2<423::AID-ANIE423>3.0.CO;2-6)
Articles
- Alaboosh, J. M. H., Hill, S. P., Kariuki, B. M. and Redman, J. E. 2024. Crystal structures of sulfonamide protected bicyclic guanidines: (S)-8-{[(tert-butyldimethylsilyl)oxy]methyl}-1-[(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl]-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidin-1-ium trifluoromethanesulfonate and (S)-8-(iodomethyl)-1-tosyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidin-1-ium iodide. Acta Crystallographica Section E: Crystallographic Communications 80(3), pp. 305-309. (10.1107/S2056989024001129)
- Smith, D. A., Redman, J. E., Fraser, D. J. and Bowen, T. 2023. Identification and detection of microRNA kidney disease biomarkers in liquid biopsies. Current Opinion in Nephrology and Hypertension 32(6), pp. 515-521. (10.1097/MNH.0000000000000927)
- Shepherd, F. R. et al. 2023. The superantigens SpeC and TSST-1 specifically activate TRBV12-3/12-4+ memory T cells. Communications Biology 6, article number: 78. (10.1038/s42003-023-04420-1)
- Exner, R. M., Paisey, S. J., Redman, J. E. and Pascu, S. I. 2021. Explorations into peptide nucleic acid contrast agents as emerging scaffolds for breakthrough solutions in medical imaging and diagnosis. ACS Omega 6(43), pp. 28455-28462. (10.1021/acsomega.1c03994)
- Man, S. et al. 2021. Synthetic peptides with inadvertent chemical modifications can activate potentially autoreactive T cells. The Journal of Immunology 207(4), pp. 1009-1017. (10.4049/jimmunol.2000756)
- Smith, D. A. et al. 2021. Detection of urinary microRNA biomarkers using diazo sulfonamide-modified screen printed carbon electrodes. RSC Advances 11(31), pp. 18832-18839. (10.1039/D0RA09874D)
- Smith, D., Newbury, L., Drago, G., Bowen, T. and Redman, J. E. 2017. Electrochemical detection of urinary microRNAs via sulfonamide-bound antisense hybridisation. Sensors and Actuators B: Chemical 253, pp. 335-341. (10.1016/j.snb.2017.06.069)
- Reid, R., Redman, J. E., Rizkallah, P., Fegan, C. D., Pepper, C. J. and Man, S. T. 2015. CD8+ T-cell recognition of a synthetic epitope formed by t-butyl modification. Immunology 144(3), pp. 495-505. (10.1111/imm.12398)
- Möschwitzer, V. D., Kariuki, B. and Redman, J. E. 2013. Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids. Tetrahedron Letters 54(34), pp. 4526-4528. (10.1016/j.tetlet.2013.06.066)
- Michael, D. R. et al. 2011. The human hyaluronan synthase 2 (HAS2) gene and its natural antisense RNA exhibit coordinated expression in the renal proximal tubular epithelial cell. Journal of Biological Chemistry 286(22), pp. 19523-19532. (10.1074/jbc.M111.233916)
- Rouziere, A. and Redman, J. E. 2011. A practical workshop for generating simple DNA fingerprints of plants. Biochemistry and Molecular Biology Education 39(3), pp. 204-210. (10.1002/bmb.20486)
- Jenkins, R. H., Bennagi, R., Martin, J., Phillips, A. O., Redman, J. E. and Fraser, D. J. 2010. A conserved stem loop motif in the 5'Untranslated Region regulates transforming growth factor-β1 translation. PLoS One 5(8), article number: e12283. (10.1371/journal.pone.0012283)
- Redman, J. E., Granadino-Roldán, J. M., Schouten, J. A., Ladame, S., Reszka, A. P., Neidle, S. and Balasubramanian, S. 2009. Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates. Organic & Biomolecular Chemistry 7(1), pp. 76-84. (10.1039/b814682a)
- Redman, J. E. 2007. Surface plasmon resonance for probing quadruplex folding and interactions with proteins and small molecules. Methods 43(4), pp. 302-312. (10.1016/j.ymeth.2007.05.008)
- Ladame, S., Schouten, J. A., Roldan, J., Redman, J. E., Neidle, S. and Balasubramanian, S. 2006. Exploring the Recognition of Quadruplex DNA by an Engineered Cys2-His2 Zinc Finger Protein. Biochemistry 45(5), pp. 1393-1399. (10.1021/bi050229x)
- Yadav, M. K., Redman, J. E., Leman, L. J., Alvarez-Gutiérrez, J. M., Zhang, Y., Stout, C. D. and Ghadiri, M. R. 2005. Structure-Based Engineering of Internal Cavities in Coiled-Coil Peptides. Biochemistry 44(28), pp. 9723-9732. (10.1021/bi050742a)
- Redman, J. E., Wilcoxen, K. M. and Ghadiri, M. R. 2002. Automated mass spectrometric sequence determination of cyclic peptide library members. Journal of Combinatorial Chemistry 5(1), pp. 33-40. (10.1021/cc0200639)
- Cousins, G. R. L., Furlan, R. L. E., Ng, Y., Redman, J. E. and Sanders, J. K. M. 2001. Identification and Isolation of a Receptor for N-Methyl Alkylammonium Salts: Molecular Amplification in a Pseudo-peptide Dynamic Combinatorial Library. Angewandte Chemie International Edition 40(2), pp. 423-428. (10.1002/1521-3773(20010119)40:2<423::AID-ANIE423>3.0.CO;2-6)
- Möschwitzer, V. D., Kariuki, B. and Redman, J. E. 2013. Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids. Tetrahedron Letters 54(34), pp. 4526-4528. (10.1016/j.tetlet.2013.06.066)
- Michael, D. R. et al. 2011. The human hyaluronan synthase 2 (HAS2) gene and its natural antisense RNA exhibit coordinated expression in the renal proximal tubular epithelial cell. Journal of Biological Chemistry 286(22), pp. 19523-19532. (10.1074/jbc.M111.233916)
- Jenkins, R. H., Bennagi, R., Martin, J., Phillips, A. O., Redman, J. E. and Fraser, D. J. 2010. A conserved stem loop motif in the 5'Untranslated Region regulates transforming growth factor-β1 translation. PLoS One 5(8), article number: e12283. (10.1371/journal.pone.0012283)
- Redman, J. E., Granadino-Roldán, J. M., Schouten, J. A., Ladame, S., Reszka, A. P., Neidle, S. and Balasubramanian, S. 2009. Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates. Organic & Biomolecular Chemistry 7(1), pp. 76-84. (10.1039/b814682a)
Research
- Protein engineering using phage display
- Development of synthetic small molecule ligands for folded nucleic acids
- Design of assays for probing interactions of ligands with nucleic acids
- Computer assisted mass spectrometric structure determination of combinatorial library products
- Application of solid phase chemistry for preparation of topologically diverse compounds
An understanding of the forces between molecules enables us to design synthetic compounds that interact with biological targets and to redesign natural biomolecules to achieve new functions. One of our research interests concerns the engineering of small molecule binding sites within proteins and in this area we are using phage display techniques to select for allosteric drug binding sites in zinc-finger transcription factor proteins.
Nucleic acids, and especially RNA, can adopt complex folded structures comparable to proteins and we are involved with development of small molecule ligands against these macromolecular targets. In order to realize our designs we need to call upon the skills of synthetic organic chemistry for preparation and assembly of molecular building blocks. We are currently synthesising a range of amino acids with guanidine side chains as building blocks for nucleic acid binding peptides.
One of our goals is to increase the efficiency with which we discover new ligands through a combination of miniaturized parallel synthesis and analysis to verify the identity of reaction products. We have a particular interest in the application of tandem mass spectrometry and computer assisted structure determination of peptides with unnatural topologies, including cyclic, branched and cross linked molecules. We are developing software for structure determination of these compounds using an automated analysis of fragmentation patterns. These classes of compound are amenable to parallel synthesis, and through a judicious choice of building blocks we can tune them to exhibit a desired biological activity such as selective recognition of a nucleic acid fold.
Teaching
CH0003 Chemistry of Organic Compounds
CH3216 Chemical Biology II: Introduction to Enzyme and Nucleic Acid Chemistry
CH3217 Biomolecular Chemistry
CH2317 Chemical Biology III: Biosynthetic Approach to Natural Products
CH3405 Organic Chemistry 2
CHT224 Medicinal Chemistry
CHT207 Biosynthetic Approach to Natural Products
CHT232 Key Skills for Postgraduate Chemists
Biography
PhD University of Cambridge (2000, J. K. M. Sanders, self-assembly of porphyrins). Wellcome Trust Travelling Research Fellowship (2000-3). Research Fellow, Scripps Research Institute (2000-2, M. R. Ghadiri, protein design and mass spectrometry of cyclic peptides). Research Associate, University of Cambridge (2002-6, S. Balasubramanian, recognition of guanine quadruplexes by proteins and small molecules). Appointed as Lecturer, Cardiff, in 2006.