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Martin Tanner

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Research and Teaching Interests

Our efforts focus on developing a detailed understanding of the mechanisms by which enzymes catalyze biological reactions. Insights obtained from studies on enzyme mechanism can lead to the production of bio-active compounds and to the design of efficient synthetic catalysts.

 Stereochemical control is a key component in the biosynthesis and metabolism of many biological compounds. As a result, many racemases and epimerases have evolved that catalyze the inversion of configuration about carbon. Most of these enzymes act at centers which are activated by an adjacent carbonyl functionality, and they abstract a relatively acidic proton. Our interests lie in studying enzymes that act on unactivated stereocenters and must employ unique reaction mechanisms. One example is ADP-heptose 6-epimerase that generates a key building block in bacterial lipopolysaccharide biosynthesis.

Another area of current interest in the Tanner group are the enzymes responsible for the biosynthesis of the sialic acids in mammals. Sialic acids are found on the surface of mammalian cells and play key roles in mediating cellular recognition events. Studies on both the epimerase and the synthase are currently ongoing in the lab.

Sialic Acid Biosynthesis in Mammels

 A wide range of experimental techniques are used to probe the reaction pathways. The tools of physical organic chemistry, such as isotopic labeling studies and the measurement of kinetic isotope effects, help to outline the order of, and the barriers to, the bond-making and bond-breaking steps in these transformations. Synthetic organic chemistry is used to prepare unnatural substrates that will serve as potent enzyme inhibitors (transition state analogs) or as mechanism-based enzyme inactivators (suicide substrates). Finally, the tools of molecular biology are used to produce large quantities of enzyme and to perform site-directed mutagenesis experiments.

 

Tanner Group

Contact

Real name: 
Martin Tanner
Email: 
Office Room Number(s): 
Chemistry A241
Office Phone Number: 
604-822-9453
Fax Number: 
604-822-2847

Curriculum Vitae

B.Sc., University of Alberta, 1985; Ph.D., University of California, Los Angeles (D.J.Cram, 1990); NSERC Postdoctoral Fellow, Harvard University (J.R.Knowles, 1990-1992)

Publications

In Press

Sverak, H. ; Yaeger, L. N. ; Worrall, L. J. ; Vacariu, C. M. ; Glenwright, A. J. ; Vuckovic, M. ; Azawi, Z. D. Al; Lamers, R. P. ; Marko, V. A. ; Skorupski, C. ; Soni, A. S. ; Tanner, M. E. ; Burrows, L. L. ; Strynadka, N. C. J. Cryo-Em, Biochemical And Cellular Characterization Of The Anydromuropeptide Permease Ampg Central To Bacterial Fitness And Β-Lactam Antibiotic Resistance. Nat. Commun. In Press.

2024

Chen, J. ; Zehr, E. A. ; Gruschus, J. ; Szyk, A. ; Liu, Y. ; Tanner, M. E. ; Tjandra, N. ; Roll-Mecak, A. Tubulin Code Eraser Ccp5 Recognizes Branch Glutamates Through Substrate Deformation. Nature 2024, 631, 905-912.

2023

Voskoboinyk, D. ; Mahmoodi, N. ; Lin, C. S. - H. ; Murphy, M. E. P. ; Tanner, M. E. Aldehyde-Based Inhibitors Of The Peptidoglycan O-Acetylesterase Ape. ChemBioChem 2023, 24, e202300205.

2022

Zhuang, Z. ; Cummings, S. W. ; Roll-Mecak, A. ; Tanner, M. E. Phosphinic Acid-Based Inhibitors Of Tubulin Polyglycylation. Chem. Commun. 2022, 58, 6530-6533.
Vacariu, C. M. ; Tanner, M. E. Recent Advances In The Synthesis And Biological Applications Of Peptidoglycan Fragments. Chem. Eur. J. 2022, 28, e202200788.
Zhuang, Z. ; Li, M. ; Tanner, M. E. A Guanidinium Group Is An Effective Mimic Of The Tertiary Carbocation Formed By Isopentenyl Diphosphate Isomerase. Bioorg. Med. Chem. Lett. 2022, 75, 128971.

2021

Lin, C. S. - H. ; Chan, A. C. K. ; Vermeulen, J. ; Brockerman, J. ; Soni, A. S. ; Tanner, M. E. ; Gaynor, E. C. ; McIntosh, L. P. ; Simorre, J. - P. ; Murphy, M. E. P. Peptidoglycan Binding By A Pocket On The Accessory Ntf2-Domain Of Pgp2 Directs Helical Shape Of Campylobacter Jejuni. J. Biol. Chem. 2021, in press.

2020

Soni, A. S. ; Vacariu, C. M. ; Chen, J. Y. ; Tanner, M. E. Synthesis Of A Meso-Oxa-Diaminopimelic Acid-Containing Peptidoglycan Pentapeptide And Coupling To The Glcnac-Anhydro-Murnac Disaccharide. Org. Lett. 2020, 22, 2313-2317.
Adak, T. ; Morales, L. D. ; Cook, A. J. ; Grigg, J. C. ; Murphy, M. E. P. ; Tanner, M. E. Arnd Is A Deformylase Involved In Polymyxin Resistance. Chem. Commun. 2020, 56, 6830-6833.
Mahalingan, K. K. ; Keenen, E. K. ; Strickland, M. ; Li, Y. ; Liu, Y. ; Ball, H. L. ; Tanner, M. E. ; Tjandra, N. ; Roll-Mecak, A. Structural Basis For Polyglutamate Chain Initiation And Elongation By Ttll Family Enzymes. Nat. Struct. Mol. Biol. 2020, 27, 802-813.
Abdelmagid, W. M. ; Mahmoodi, N. ; Tanner, M. E. A Guanidinium-Based Inhibitor Of A Type I Isopentenyl Diphosphate Isomerase. Bioorg. Med. Chem. Lett. 2020, 30, 127577.

2019

Soni, A. S. ; Lin, C. S. - H. ; Murphy, M. E. P. ; Tanner, M. E. Peptides Containing Meso-Oxa-Diaminopimelic Acid As Substrates For The Cell-Shape-Determining Proteases Csd6 And Pgp2. ChemBioChem 2019, 20, 1591-1598.

2018

Abdelamagid, W. M. ; Adak, T. ; Freeman, J. O. ; Tanner, M. E. Studies With Guanidinium- And Amidinium-Based Inhibitors Suggest Minimal Stabilization Of Allylic Carbocation Intermediates By Dehydrosqualene And Squalene Synthases. Biochemistry 2018, 57, 5591.

2016

Liu, Y. ; Frirdich, E. ; Taylor, J. A. ; Chan, A. C. K. ; Blair, K. M. ; Vermeulen, J. ; Ha, R. ; Murphy, M. E. P. ; Salama, N. R. ; Gaynor, E. C. ; Tanner, M. E. A Bacterial Cell Shape-Determining Inhibitor. ACS Chem. Biol. 2016, 11, 981.

2015

Chan, A. C. K. ; Blair, K. M. ; Liu, Y. ; Frirdich, E. ; Gaynor, E. C. ; Tanner, M. E. ; Salama, N. R. ; Murphy, M. E. P. Helical Shape Of Helicobacter Pylori Requires An Atypical Glutamine As A Zinc Ligand In The Carboxypeptidase Csd4. JOURNAL OF BIOLOGICAL CHEMISTRY 2015, 290, 3622-3638.
Tanner, M. E. Mechanistic Studies On The Indole Prenyltransferases. NATURAL PRODUCT REPORTS 2015, 32, 88-101.
Tanner, M. E. Increasing The Diversity Of Known Pictet-Spenglerases. Chem. Biol. 2015, 22.

2014

Awakawa, T. ; Zhang, L. ; Wakimoto, T. ; Hoshino, S. ; Mori, T. ; Ito, T. ; Ishikawa, J. ; Tanner, M. E. ; Abe, I. A Methyltransferase Initiates Terpene Cyclization In Teleocidin B Biosynthesis. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2014, 136, 9910-9913.

2013

Miyafusa, T. ; Caaveiro, J. M. M. ; Tanaka, Y. ; Tanner, M. E. ; Tsumoto, K. Crystal Structure Of The Capsular Polysaccharide Synthesizing Protein Cape Of Staphylococcus Aureus. Bioscience Reports 2013, 336128294328, 463 - 474.
Hadi, T. ; Hazra, S. ; Tanner, M. E. ; Blanchard, J. S. Structure Of Murnac 6-Phosphate Hydrolase (Murq) From Haemophilus Influenzae With A Bound Inhibitor. Biochemistry 2013, 52.
Mahmoodi, N. ; Qian, Q. ; Luk, L. Y. P. ; Tanner, M. E. Rearrangements In The Mechanisms Of Indole Alkaloid Prenyltranferases. Pure App. Chem. 2013, 85.
Liu, Y. ; Garnham, C. P. ; Roll-Mecak, A. ; Tanner, M. E. Phosphinic Acid-Based Inhibitors Of Tubulin Polyglutamylases. Bioorganic & Medicinal Chemistry Letters 2013, 23, 4408 - 4412.
Mahmoodi, N. ; Tanner, M. E. Potential Rearrangements In The Reaction Catalyzed By The Indole Prenyltransferase Ftmpt1. ChemBioChem 2013, 14, 2029 - 2037.
Goble, A. M. ; Toro, R. ; Li, X. ; Ornelas, A. ; Fan, H. ; Eswaramoorthy, S. ; Patskovsky, Y. ; Hillerich, B. ; Seidel, R. ; Sali, A. ; Shoichet, B. K. ; Almo, S. C. ; Swaminathan, S. ; Tanner, M. E. ; Raushel, F. M. Deamination Of 6-Aminodeoxyfutalosine In Menaquinone Biosynthesis By Distantly Related Enzymes. Biochemistry 2013, 52, 6525 - 6536.

2012

Otto, N. J. ; Green, D. E. ; Masuko, S. ; Mayer, A. ; Tanner, M. E. ; Linhardt, R. J. ; Deangelis, P. L. Structure/function Analysis Of The Pasteurella Multocida Heparosan Synthases: Towards Defining Enzyme Specificity And Engineering Novel Catalysts. The Journal of biological chemistry 2012.
Qian, Q. ; Schultz, A. W. ; Moore, B. S. ; Tanner, M. E. Mechanistic Studies On Cymd: A Tryptophan Reverse N -Prenyltransferase. Biochemistry 2012, 51, 7733 - 7739.

2011

Mayer, A. ; Gloster, T. M. ; Chou, W. K. ; Vocadlo, D. J. ; Tanner, M. E. 6"-Azido-6"-Deoxy-Udp-N-Acetylglucosamine As A Glycosyltransferase Substrate. Bioorganic & Medicinal Chemistry Letters 2011, 21, 1199 - 1201.
Luk, L. Y. P. ; Qian, Q. ; Tanner, M. E. A Cope Rearrangement In The Reaction Catalyzed By Dimethylallyltryptophan Synthase?. Journal of the American Chemical Society 2011, 133, 12342 - 12345.
Li, X. ; Apel, D. ; Gaynor, E. C. ; Tanner, M. E. 5’-Methylthioadenosine Nucleosidase Is Implicated In Playing A Key Role In A Modified Futalosine Pathway For Menaquinone Biosynthesis In Campylobacter Jejuni. Journal of Biological Chemistry 2011, 286, 19392 - 19398.
Hadi, T. ; Pfeffer, J. M. ; Clarke, A. J. ; Tanner, M. E. Water-Soluble Substrates Of The Peptidoglycan-Modifying Enzyme O- Acetylpeptidoglycan Esterase (Ape1) From Neisseria Gonorrheae. The Journal of Organic Chemistry 2011, 76, 1118 - 1125.

2010

Li, X. ; Tanner, M. E. An Efficient Synthesis Of Futalosine. Tetrahedron Letters 2010, 51, 6463 - 6465.
Kowatz, T. ; Morrison, J. P. ; Tanner, M. E. ; Naismith, J. H. The Crystal Structure Of The Y140F Mutant Of Adp-L-Glycero-D-Manno-Heptose 6-Epimerase Bound To Adp-Β-D-Mannose Suggests A One Base Mechanism. Protein Science 2010, 19, 1337 - 1343.

2009

Liu, F. ; Lee, H. J. ; Strynadka, N. C. J. ; Tanner, M. E. Inhibition Of Neisseria Meningitidis Sialic Acid Synthase By A Tetrahedral Intermediate Analogue. Biochemistry 2009, 48, 9194-9201.
Luk, L. Y. P. ; Tanner, M. E. Mechanism Of Dimethylallyltryptophan Synthase: Evidence For A Dimethylallyl Cation Intermediate In An Aromatic Prenyltransferase Reaction. Journal of the American Chemical Society 2009, 131, 13932-13933.
Liu, F. ; Aubry, A. J. ; Schoenhofen, I. C. ; Logan, S. M. ; Tanner, M. E. The Engineering Of Bacteria Bearing Azido-Pseudaminic Acid-Modified Flagella. Chembiochem 2009, 10, 1317-1320.

2008

Tanner, M. E. Transient Oxidation As A Mechanistic Strategy In Enzymatic Catalysis. Current Opinion in Chemical Biology 2008, 12, 532-538.
Hadi, T. ; Dahl, U. ; Mayer, C. ; Tanner, M. E. Mechanistic Studies On N-Acetylmuramic Acid 6-Phosphate Hydrolase (Murq): An Etherase Involved In Peptidoglycan Recycling. Biochemistry 2008, 47, 11547-11558.
Glaze, P. A. ; Watson, D. C. ; Young, N. M. ; Tanner, M. E. Biosynthesis Of Cmp-N,n’-Diacetyllegionaminic Acid From Udp-N,n’-Diacetylbacillosamine In Legionella Pneumophila. Biochemistry 2008, 47, 3272-3282.
Lau, S. T. B. ; Tanner, M. E. Mechanism And Active Site Residues Of Gdp-Fucose Synthase. Journal of the American Chemical Society 2008, 130, 17593-17602.
Morrison, J. P. ; Schoenhofen, I. C. ; Tanner, M. E. Mechanistic Studies On Pseb Of Pseudaminic Acid Biosynthesis: A Udp-N-Acetylglucosamine 5-Inverting 4,6-Dehydratase. Bioorganic Chemistry 2008, 36, 312-320.

2007

Morrison, J. P. ; Tanner, M. E. A Two-Base Mechanism For Escherichia Coli Adp-L-Glycero-D-Manno-Heptose 6-Epimerase. Biochemistry 2007, 46, 3916-3924.
Luk, L. Y. P. ; Bunn, S. ; Liscombe, D. K. ; Facchini, P. J. ; Tanner, M. E. Mechanistic Studies On Norcoclaurine Synthase Of Benzylisoquinoline Alkaloid Biosynthesis: An Enzymatic Pictet-Spengler Reaction. Biochemistry 2007, 46, 10153-10161.
Mayer, A. ; Tanner, M. E. Intermediate Release By Adp-L-Glycero-D-Manno-Heptose 6-Epimerase. Biochemistry 2007, 46, 6149-6155.

2006

Liu, F. ; Tanner, M. E. Pseg Of Pseudaminic Acid Biosynthesis - A Udp-Sugar Hydrolase As A Masked Glycosyltransferase. Journal of Biological Chemistry 2006, 281, 20902-20909.

2005

Chou, W. K. ; Dick, S. ; Wakarchuk, W. W. ; Tanner, M. E. Identification And Characterization Of Neub3 From Campylobacter Jejuni As A Pseudaminic Acid Synthase. Journal of Biological Chemistry 2005, 280, 35922-35928.
Read, J. A. ; Ahmed, R. A. ; Tanner, M. E. Efficient Chemoenzymatic Synthesis Of Adp-D-Glycero-Beta-D-Manno-Heptose And A Mechanistic Study Of Adp-L-Glycero-D-Manno-Heptose 6-Epimerase. Organic Letters 2005, 7, 2457-2460.
Tanner, M. E. The Enzymes Of Sialic Acid Biosynthesis. Bioorganic Chemistry 2005, 33, 216-228.
Gunawan, J. ; Simard, D. ; Gilbert, M. ; Lovering, A. L. ; Wakarchuk, W. W. ; Tanner, M. E. ; Strynadka, N. C. J. Structural And Mechanistic Analysis Of Sialic Acid Synthase Neub From Neisseria Meningitidis In Complex With Mn2+ Phosphoenolpyruvate, And N-Acetylmannosaminitol. Journal of Biological Chemistry 2005, 280, 3555-3563.
Morrison, J. P. ; Read, J. A. ; Coleman, W. G. ; Tanner, M. E. Dismutase Activity Of Adp-L-Glycero-D-Manno-Heptose 6-Epimerase: Evidence For A Direct Oxidation/reduction Mechanism. Biochemistry 2005, 44, 5907-5915.

2004

Murkin, A. S. ; Chou, W. K. ; Wakarchuk, W. W. ; Tanner, M. E. Identification And Mechanism Of A Bacterial Hydrolyzing Udp-N-Acetylglucosamine 2-Epimerase. Biochemistry 2004, 43, 14290-14298.
Samuel, J. ; Tanner, M. E. Active Site Mutants Of The "non-Hydrolyzing" Udp-N-Acetylglucosamine 2-Epimerase From Escherichia Coli. Biochimica Et Biophysica Acta-Proteins and Proteomics 2004, 1700, 85-91.
Read, J. A. ; Ahmed, R. A. ; Morrison, J. P. ; Coleman, W. G. ; Tanner, M. E. The Mechanism Of The Reaction Catalyzed By Adp-Beta-L-Glycero-D-Manno-Heptose 6-Epimerase. Journal of the American Chemical Society 2004, 126, 8878-8879.
Ge, X. ; Penney, L. C. ; van de Rijn, I. ; Tanner, M. E. Active Site Residues And Mechanism Of Udp-Glucose Dehydrogenase. European Journal of Biochemistry 2004, 271, 14-22.
Vann, W. F. ; Daines, D. A. ; Murkin, A. S. ; Tanner, M. E. ; Chaffin, D. O. ; Rubens, C. E. ; Vionnet, J. ; Silver, R. P. The Neuc Protein Of Escherichia Coli K1 Is A Udp N-Acetylglucosamine 2-Epimerase. Journal of Bacteriology 2004, 186, 706-712.

2003

Chou, W. K. ; Hinderlich, S. ; Reutter, W. ; Tanner, M. E. Sialic Acid Biosynthesis: Stereochemistry And Mechanism Of The Reaction Catalyzed By The Mammalian Udp-N-Acetylglucosamine 2-Epimerase. Journal of the American Chemical Society 2003, 125, 2455-2461.

2002

Tanner, M. E. Understanding Nature’S Strategies For Enzyme-Catalyzed Racemization And Epimerization. Accounts of Chemical Research 2002, 35, 237-246.
Murkin, A. S. ; Tanner, M. E. Dehydroalanine-Based Inhibition Of A Peptide Epimerase From Spider Venom. Journal of Organic Chemistry 2002, 67, 8389-8394.
Samuel, J. ; Tanner, M. E. Mechanistic Aspects Of Enzymatic Carbohydrate Epimerization. Natural Product Reports 2002, 19, 261-277.
Tanner, M. E. ; Chou, W. K. ; Reutter, W. ; Hinderlich, S. Stereochemistry And Mechanism Of The Reaction Catalyzed By The Mammalian Udp-Glcnac 2-Epimerase. Biochemistry 2002, 41, 82.

2001

Glavas, S. ; Tanner, M. E. Active Site Residues Of Glutamate Racemase. Biochemistry 2001, 40, 6199-6204.
Tanner, M. E. Sugar Nucleotide-Modifying Enzymes. Current Organic Chemistry 2001, 5, 169-192.
Samuel, J. ; Luo, Y. ; Morgan, P. M. ; Strynadka, N. C. J. ; Tanner, M. E. Catalysis And Binding In L-Ribulose-5-Phosphate 4-Epimerase: A Comparison With L-Fuculose-1-Phosphate Aldolase. Biochemistry 2001, 40, 14772-14780.
Luo, Y. ; Samuel, J. ; Mosimann, S. C. ; Lee, J. E. ; Tanner, M. E. ; Strynadka, N. C. J. The Structure Of L-Ribulose-5-Phosphate 4-Epimerase: An Aldolase-Like Platform For Epimerization. Biochemistry 2001, 40, 14763-14771.

2000

Campbell, R. E. ; Mosimann, S. C. ; van de Rijn, I. ; Tanner, M. E. ; Strynadka, N. C. J. The First Structure Of Udp-Glucose Dehydrogenase Reveals The Catalytic Residues Necessary For The Two-Fold Oxidation. Biochemistry 2000, 39, 7012-7023.
Tanner, M. E. ; Campbell, R. E. ; Ge, X. ; Mossiman, S. ; Strynadka, N. C. J. Covalent Catalysis With Udp-Glucose Dehydrogenase. Biochemistry 2000, 39, 2.
Campbell, R. E. ; Mosimann, S. C. ; Tanner, M. E. ; Strynadka, N. C. J. The Structure Of Udp-N-Acetylglucosamine 2-Epimerase Reveals Homology To Phosphoglycosyl Transferases. Biochemistry 2000, 39, 14993-15001.

1999

Galpin, J. D. ; Ellis, B. E. ; Tanner, M. E. The Inactivation Of Histidine Ammonia-Lyase By L-Cysteine And Oxygen: Modification Of The Electrophilic Center. Journal of the American Chemical Society 1999, 121, 10840-10841.
Glavas, S. ; Tanner, M. E. Catalytic Acid/base Residues Of Glutamate Racemase. Biochemistry 1999, 38, 4106-4113.
Campbell, R. E. ; Tanner, M. E. Udp-Glucose Analogues As Inhibitors And Mechanistic Probes Of Udp-Glucose Dehydrogenase. Journal of Organic Chemistry 1999, 64, 9487-9492.

1998

Ge, X. ; Campbell, R. E. ; van de Rijn, I. ; Tanner, M. E. Covalent Adduct Formation With A Mutated Enzyme: Evidence For A Thioester Intermediate In The Reaction Catalyzed By Udp-Glucose Dehydrogenase. Journal of the American Chemical Society 1998, 120, 6613-6614.
Sala, R. F. ; MacKinnon, S. L. ; Palcic, M. M. ; Tanner, M. E. Udp-N-Trifluoroacetylglucosamine As An Alternative Substrate In N-Acetylglucosaminyltransferase Reactions. Carbohydrate Research 1998, 306, 127-136.
Zeng, B. Q. ; Kwong, K. ; Pompliano, D. L. ; Reddy, S. ; Tanner, M. E. A Phosphinate Inhibitor Of The Meso-Diaminopimelic Acid-Adding Enzyme (Mure) Of Peptidoglycan Biosynthesis. Journal of Organic Chemistry 1998, 63, 10081-10085.
Johnson, A. E. ; Tanner, M. E. Epimerization Via Carbon-Carbon Bond Cleavage. L-Ribulose-5-Phosphate 4-Epimerase As A Masked Class Ii Aldolase. Biochemistry 1998, 37, 5746-5754.

1997

Morgan, P. M. ; Sala, R. F. ; Tanner, M. E. Eliminations In The Reactions Catalyzed By Udp-N-Acetylglucosamine 2-Epimerase. Journal of the American Chemical Society 1997, 119, 10269-10277.
Campbell, R. E. ; Sala, R. F. ; vandeRijn, I. V. ; Tanner, M. E. Properties And Kinetic Analysis Of Udp-Glucose Dehydrogenase From Group A Streptococci - Irreversible Inhibition By Udp-Chloroacetol. Journal of Biological Chemistry 1997, 272, 3416-3422.
Campbell, R. E. ; Tanner, M. E. Uridine Diphospho-Alpha-D-Gluco-Hexodialdose: Synthesis And Kinetic Competence In The Reaction Catalyzed By Udp-Glucose Dehydrogenase. Angewandte Chemie-International Edition in English 1997, 36, 1520-1522.
Glavas, S. ; Tanner, M. E. The Inhibition Of Glutamate Racemase By D-N-Hydroxyglutamate. Bioorganic & Medicinal Chemistry Letters 1997, 7, 2265-2270.

1996

Sala, R. F. ; Morgan, P. M. ; Tanner, M. E. Enzymatic Formation And Release Of A Stable Glycal Intermediate: The Mechanism Of The Reaction Catalyzed By Udp-N-Acetylglucosamine 2-Epimerase. Journal of the American Chemical Society 1996, 118, 3033-3034.
Tanner, M. E. ; Vaganay, S. ; vanHeijenoort, J. ; Blanot, D. Phosphinate Inhibitors Of The D-Glutamic Acid-Adding Enzyme Of Peptidoglycan Biosynthesis. Journal of Organic Chemistry 1996, 61, 1756-1760.

1994

Tanner, M. E. ; Miao, S. C. The Synthesis And Stability Of Aziridino-Glutamate, An Irreversible Inhibitor Of Glutamate Racemase. Tetrahedron Letters 1994, 35, 4073-4076.
Abdelmagid, W. M. ; Mahmoodi, N. ; Tanner, M. E. A Guanidinium-Based Inhibitor Of A Type I Isopentenyl Diphosphate Isomerase. Bioorg. Med. Chem. Lett.