Publications
2024
Genova, L. A.; Procko, K.; Grimes, C. L.; Williams, C.; Cornely, K.; Shor, A.; Greene, A. S.; Bibel, B.; Kumar, S. V.; White, H. B. Glycolysis Can Be Fun: Rediscovering Glycolysis as a Problem-Solving Introduction to Metabolism. CourseSource 2024, 11
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Putnik, R.; Zhou, J.; Irnov, I.; Garner, E.; Liu, M.; Bersch, K. L.; Jacobs-Wagner, C.; Grimes, C. L. Synthesis of a Borrelia burgdorferi-Derived Muropeptide Standard Fragment Library. Molecules 2024, 29, 3297
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*Hillman, A.S.; *Hyland, S.N.; *Wodzanowski, K.A.; Moore, D.L.; Ratna, S.; Jemas, A.;Sandles, L.M.; Chaya, T.; Ghosh, A.; Fox, J.M.; Grimes, C.L.; Minimalist Tetrazine N-Acetyl Muramic Acid Proes for Rapid and Efficient Labeling of Commensal and Pathogenic Peptidoglycans in Living Bacterial Culture and During Macrophage Invasion. JACS 2024, 146, 10, 6817-6829
2023
*Bharadwaj, R.; *Anonick, M.V.; Jaiswal, S.; Mashayekh, S.; Brown, A.; Wodzanowski, K.A.; Okuda, K.; Silverman, N.; Grimes, C.L.; Synthesis and validation of click-modified NOD 1/2 agonists. Innate Immunity 2023, 29(8);186-200.
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Hyland, S.N.; Chinthamani, S.; Ratna, S.; Wodzanowski, K.A.; Sandles, L.M.; Honma, K.; Grimes, C.L.; Sharma, A.; Biorthogonal Labeling and Click-Chemistry Based Visualization of the Tannerella forsythia Cell Wall. Methods in Molecular Biology 2023, vol 2727.
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Ghosh, S.; Ahearn, C.P.; Isabella, C.R.; Marando, V.M.; Dodge, G.J.; Bartlett, H.; McPherson, R.L.; Dugan, A.E.; Jain, S.; Neznanova, L.; Tettelin, H.; Putnik, R.; Grimes, C.L.; Ruhl, S.; Kiessling, L.L.; Imperialli, B.; Human oral lectin ZG16B acts as a cell wall polysaccharide probe to decode host-microbe interactions with oral commensals. PNAS 2023, 120 (22) e2216304120.
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Bharadwaj, R.; Lusi, C.F.; Mashayekh, S.; Nagar, A.; Subbarao, M.; Kane, G.I.; Wodzanowski, K.A.; Brown, A.R.; Okuda, K.; Monahan, A.; Paik, D.; Nandy, A.; Anonick, M.V.; Goldman, W.E.; Kanneganti, T.D.; Orzalli, M.H.; Grimes, C.L.; Atukorale, P.U.; Silverman, N; Methotrexate suppresses psoriatic skin inflammation by inhibiting muropeptide transporter SLC46A2 activity. Immunity 2023, 56, 1-15.
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Le, H.T.; Liu, M.; Grimes, C.L.; Application of bioanalytical and computational methods in decoding the roles of glycans in host-pathogen interactions. Current Opinion in Chemical Biology 2023, 74, 102301.
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Wodzanowski, K.A.; Anonick, M.V.; Genova, L.A.; Kloxin, A.M.; Grimes, C.L.; Bringing Pasteur Back to Life: Studying the Biochemistry of Yeast Fermentation Through Discussion Groups and an At-Home Lab. CourseSource 2023, 10.
2022
Lund, V.A.; Gangotra, H.; Zhao, Z.; Sutton, J.A.F.; Wacnik, K.; DeMeester, K.; Liang, H.; Santiago, C.; Grimes, C.L.; Jones, S.; Foster, S.J.; Coupling Novel Probes with Molecular Localization Microscopy Reveals Cell Wall Homeostatic Mechanisms in Staphylococcus aureus. ACS Chemical Biology 2022, 17, 12, 3298-3305.
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Wodzanowski, K.A.; Hyland, S.N.; Chinthamani, S.; Sandles, LM.D.; Honma, K.; Sharma, A.; Grimes, C.L.; Investigating Peptidoglycan Recycling Pathways in Tannerella forsythia with N-Acetylmuramic Acid Bioorthogonal Probes. ACS Infectious Diseases 2022, 8, 9, 1831-1838.
*Highlighted in ACS Central Science Bioorthogonal and Click Chemistry Virtual Issue curated by Prof. Carolyn R. Bertozzi, 2022 winner of the Nobel Prize in Chemistry
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Crump, G.M.; Rozovsky, S.; Grimes, C.L.; Purification and Characterization of a Stable, Membrane-Associated Peptidoglycan Responsive Adenylate Cyclase LRR Domain from Human Commensal Candida albicans. Biochemistry 2022, 61, 24, 2856-2860
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Wodzanowski, K.A.; Caplan, J.L.; Kloxin, A.M.; Grimes, C.L.; Multiscale Invasion Assay for Probing Macrophage Response to Gram-Negative Bacteria. Frontiers in Chemistry: Chemical Biology 2022.
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Le, H.T.; D’Ambrosio, E.A.; Mashayekh, S.; Grimes, C.L.; Customized peptidoglycan surfaces to investigate innate immune recognition via surface plasmon resonance. Methods in Enzymology 2022.
2021
Brown, A.R.; Wodzanowski, K.A.; Santiago, C.C.; Hyland, S.N.; Follmar, J.L.; Asare-Okai, P; Grimes, C.L.; Protected N-Acetyl Muramic Acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling. ACS Chemical Biology 2021, 16, 10, 1908–1916.
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, , , , , ; Bacterial peptidoglycan fragments differentially regulate innate immune signaling. ACS Central Science 2021
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Scherzi T.; D’Ambrosio, E.A.; Daher, S.S.; Grimes, C.L.; Dunman, P.M.; Andrade, R.B. Staphylococcus aureus resistance to albocycline can be achieved by mutations that alter cellular NAD/PH pools. Biorg. Med. Chem. 2021, (32) 15, 15995
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Yang, X.; McQuillen, R.; Lyu, Z.; Phillips-Mason, P.; De La Cruz, A.; McCausland, J. W.; Liang, H.; DeMeester, K. E.; Santiago, C. C.; Grimes, C. L.; de Boer, P.; Xiao, J., A two-track model for the spatiotemporal coordination of bacterial septal cell wall synthesis revealed by single-molecule imaging of FtsW. Nat Microbiol 2021, 6, 584–593.
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Taylor, J.A.; Santiago, C.C.; Gray, J.; Wodzanowski, K.A.; DeMeester, K.E.; Biboy, J.; Vollmer, W.; Grimes, C.L.; Salama, N.R. Localizing peptidoglycan synthesis in Helicobacter pylori using clickable metabolic probes. Current Protocols. 2021.
2020
Mashayekh, S.; Bersch, K. L.; Ramsey, J.; Harmon, T.; Genova, L.A.; Grimes, C.L. Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments. J. Org. Chem. 2020, 85, 24, 16243–16253.
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Crump, G.M.; Zhou, J.; Mashayekh, S.; Grimes, C.L. Revisiting Peptidoglycan Signaling: Interactions with Host Immunity and Beyond. Chem. Commun. 2020, 56, 13313-13322.
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Brown, A.R.; Gordon, R.A.; Hyland, S.N.; Siegrist, M.S.; Grimes, C.L. Chemical Biology Tools for Examining the Bacterial Cell Wall. Cell. Chem. Bio. 2020, 27 (8), 1052-1062
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Ukaegbu, O.I.; DeMeester, K.E.; Liang, H.; Brown, A.R.; Jones, Z.S.; Grimes, C.L. Utility of bacterial peptidoglycan recycling enzymes in the chemoenzymatic synthesis of valuable UDP sugar substrates. Methods in Enzymology. 2020, 638, 1-26
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D’Ambrosio, E. A.; Bersch, K. L.; Lauro, M. L.; Grimes, C. L. Differential Peptidoglycan Recognition Assay Using Varied Surface Presentations. J. Am. Chem. Soc. 2020, 142 (25), 10926-10930
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Wodzanowski K. A.*; Cassel, S. E.*; Grimes, C. L., Kloxin, A. M. Tools for probing host-bacteria interactions in the gut microenvironment: From molecular to cellular levels. Bioorg. med. chem. lett. 2020, 30 (10)
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Taylor, J. A.; Bratton, B. P; Sichel, S. R.; Blair K. M.; Jacobs, H. M. DeMeester, K. E.; Gray, J.; Biboy, J.; VanNieuwenhze, M.S.; Grimes, C.L.; Shaevitz, J.W.; Salama, N.R. Distinct cytoskeletal proteins define zones of enhanced cell wall synthesis in Helicobacter pylori. elife. 2020, 9:e52482.
2019
DeMeester, K. E.*; Liang ,H.*; Zhou, J.*; Wodzanowski, K. A.*; Prather, B. L.; Santiago, C. C.; Grimes, C. L. Metabolic incorporation of N-acetyl muramic acid probes into bacterial peptidoglycan. Current Protocols in Chemical Biology. 2019, 74 (11).
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D’Ambrosio, E. A.*; Drake, W. R.*; Mashayekh, S.*; Ukaegbu, O. I.; Brown, A. R.; Grimes, C. L. Modulation of the Nod-like receptors NOD1 and NOD2: A Chemist’s Perspective. Bioorg. med. chem. lett. 2019, 29 (10), 1153-1161. Featured on cover
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Lazor, K. M.; Zhou, J; DeMeester, K. E.; D’Ambrosio, E.A.; Grimes, C.L. Synthesis and application of methyl N,O-hydroxylamine muramyl peptides. ChemBioChem. 2019, 20, 1369-1375
2018
McDonald, N. D.; DeMeester, K.E.; Lewis A.L.; Grimes, C.L. ; Boyed, E.F. Structural and functional characterization of a modified legionaminic acid involved in glycosylation of a bacterial lipopolysaccharide. J. Biol. Chem. 2018, 293 (49), 19113–19126
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Chang, P. V.; Grimes, C.L. Designer Dendrons To Dissect Innate Immune Signaling. ACS Central Science. 2018, 4 (8), 948–949
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DeMeester, K. E.; Liang, H.; Jensen M. R.; Jones, Z. S.; D’Ambrosio, E. A.; Scinto, S. L.; Zhou, J.; Grimes, C. L. Synthesis of functionalized N-acetyl muramic acids to probe bacterial cell wall recycling and biosynthesis. J. Am. Chem. Soc. 2018, 140 (30), 9458–9465
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Liang, H.; Zhou, G.; Ge, Y.; D’Ambrosio, E. A.; Eidem, T. M.; Blanchard, C.; Shehatou, C.; Chatare, V. K.; Dunman, P. M.; Valentine, A. M.; Voelz, V. A.; Grimes, C. L.; Andrade, R. B. Elucidating the inhibition of peptidoglycan biosynthesis in Staphylococcus aureus by albocycline, a macrolactone isolated from Streptomyces maizeus. Bioorganic and Medicinal Chemistry2018, 26 (12), 3453-3460
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Drake, W.R.; Hou C.W.; Zachara, N. E.; Grimes, C. L. New use for CETSA: monitoring innate immune receptor stability via post-translational modification by OGT. Journal of bioenergetics and biomembranes. 2018, 50 (3), 231-240
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Burch, J. M.; Mashayekh, S.; Wykoff, D.D.; Grimes, C.L. Bacterial Derived Carbohydrates Bind Cyr1 and Trigger Hyphal growth in Candida albicans. ACS Infectous Diseases. 2018, 4, 53-58
2017
Wang, Y.; Lazor, K. M.; DeMeester, K. E.; Liang, H.; Heiss, T. K.; Grimes, C. L. Postsynthetic Modification of Bacterial Peptidoglycan Using Bioorthogonal N-Acetylcysteamine Analogs and Peptidoglycan O-Acetyltransferase B. J. Am. Chem. Soc. 2017, 139, 13596-13599.
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Schaefer, A. K.; Wastyk, H. C.; Mohanan, V.; Hou, C. W.; Lauro, M.L.; Melnyk, J.E.; Burch, J. M.; Grimes, C. L. Crohn’s Disease Variants of Nod2 Are Stabilized by the Critical Contact Region of Hsp70. Biochemistry. 2017, 56, 4445-4448.
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Schaefer, A. K.*; Melnyk, J. E.*; Baksh, M. M.; Lazor, K. M.; Finn M. G.; Grimes, C. L. Membrane Association Dictates Ligand Specificity for the Innate Immune Receptor NOD2. ACS Chemical Biology. 2017, 12, 2216-2224.
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Liang, H.*; DeMeester, K. E.*; Hou, C. W.; Parent, M. A.; Caplan, J. L.; Grimes, C. L. Metabolic labeling of the carbohydrate core in bacterial peptidoglycan and its applications. Nature Communications. 2017, 8, 15015.
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Lauro, M. L.; D’Ambrosio, E. A.; Bahnson, B. J.; Grimes, C. L. Molecular Recognition of Muramyl Dipeptide Occurs in the Leucine-rich Repeat Domain of Nod2. ACS Infectious Diseases. 2017, 3, 264-270.
2016
Hou, C. W.; Lauro, M. L.; Grimes, C. L. “Redefining the Defensive Line: Critical Components of the Innate Immune System”, ACS Infectious Diseases. 2016, 2, 746.
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Lauro, M. L.; Burch, J.; Grimes, C. L. The effect of Nod2 on the microbiota in Crohn’s disease. Curr Opin Biotechnol. 2016, 40, 97.
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Hou, C. W.; Mohanan, V.; Zachara, N. E.; Grimes, C.L.,Identification and biological consequences of the OGlcNAc modification of the human innate immune receptor, Nod2. Glycobiology. 2016, 26, 13.
2015
Grimes, C.L.; White, H.B. Passing the Baton: Passing the Baton: Mentoring for Adoption of Active-learning Pedagogies by Research-active Junior Faculty. Biochem. Molec. Biol. Educ. 2015, 43, 345.
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Melnyk, J.E., Mohanan, V., Schaefer, A.K., Hou, C-H., Grimes, C.L., Peptidoglycan Modifications Tune the Stability and Function of the Innate Immune Receptor Nod2, JACS. 2015, 137, 6
2014
Mohanan, V., Grimes, C.L., The Molecular Chaperone HSP70 binds to and stabilizes NOD2, an important protein in Crohn’s Disease, J. Biol. Chem. 2014, 289, 18987.
2012
Grimes, C. L.*; Ariyananda, L. D.; Melnyk, J. E.; O’Shea, E. K. The Innate Immune Protein, Nod2, Binds directly to MDP, a bacterial cell wall fragment. J. Am. Chem. Soc. 2012, 134, 13535. (*CLG is corresponding author)
Leimkuhler Grimes Post-Doctoral and Graduate Publications
Grimes, C.L.; Podolsky, D.K.; O’Shea, E.K. Synthesis of Biologically Active Biotinylated Muramyl Dipeptides, Bioorg. Med. Chem. Lett. 2010. 20 (20), 6061-3.
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Hu, Y.; Al-Mestarihi, A.; Grimes, C.L.; Kahne, D.; Bachmann, B.O. A unifying nitrososynthase involved in nitrosugar biosynthesis. J. Am. Chem. Soc. 2008, 130 (47), 15756-7.
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Leimkuhler, C.; Fridman, M.; Lupoli, T.; Walker, S.; Walsh, C.T.; Kahne, D. Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A. J. Am. Chem. Soc. 2007, 129 (34), 10546-50.
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Howard-Jones, A.R., Kruger, R.G., Lu, W., Tao, J., Leimkuhler, C., Kahne, D., and Walsh, C.T., Kinetic analysis of teicoplanin glycosyltransferases and acyltransferase reveal ordered tailoring of aglycone scaffold to reconstitute mature teicoplanin. J. Am. Chem. Soc, 2007. 129 (33), 10082-3.
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Adachi, M.; Zhang, Y.; Leimkuhler, C.; Sun, B.; LaTour, J.V.; Kahne, D.E. Degradation and reconstruction of moenomycin A and derivatives: dissecting the function of the isoprenoid chain. J. Am. Chem. Soc. 2006, 128 (43), 14012-3.
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Lu, W.; Leimkuhler, C.; Gatto, G.J. Jr.; Kruger, R.G.; Oberthur, M.; Kahne, D.; Walsh, C.T. AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin A. Chem Biol. 2005. 12 (5), 527-34.
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Leimkuhler, C.; Chen, L.; Barrett, D.; Panzone, G.; Sun, B.; Falcone, B.; Oberthur, M.; Donadio, S.; Walker, S.; Kahne, D. Differential inhibition of Staphylococcus aureus PBP2 by glycopeptide antibiotics. J. Am. Chem. Soc. 2005, 127 (10), 3250-1.
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Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. T.,Glycopeptide and lipoglycopeptide antibiotics. Chem Rev. 2005, 105 (2), 425-48.
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Leimkuhler, C.; Chen, Z.; Kruger, R.G.; Oberthur, M.; Lu, W.; Walsh, C.T.; Kahne, D. Glycosylation of glycopeptides: a comparision of chemoenzymatic and chemical methods. Tetrahedron: Asymmetry. 2005, 16 (2), 599-603.
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Yuan, Y.; Chung, H.S.; Leimkuhler, C.; Walsh, C.T.; Kahne, D.; Walker, S. In Vitro Reconstitution of EryCIII Activity for the Preparation of Unnatural Macrolides. J. Am. Chem. Soc. 2005, 127 (41), 14128-14129.
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Barrett, D.; Leimkuhler, C.; Chen, L.; Walker, D.; Kahne, D.; Walker, S. Kinetic Characterization of the Glycosyltransferase Module of Staphylococcus aureus PBP2. J Bacteriol. 2005, 187 (6), 2215-7.
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Oberthur, M.; Leimkuhler, C.; Kruger, R.G.; Lu, W.; Walsh, C.T.; Kahne, D. A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases. JACS. 2005, 127(30): p. 10747-52.
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Lu, W.; Leimkuhler, C.; Oberthur, M.; Kahne, D.; Walsh, C.T. AknK is an L-2-deoxyfucosyltransferase in the biosynthesis of the anthracycline aclacinomycin A. Biochemistry. 2004, 43 (15), 4548-58.
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Lu, W.; Oberthur, M.; Leimkuhler, C.; Tao, J.; Kahne, D.; Walsh, C.T. Characterization of a regiospecific epivancosaminyl transferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin. Proc Natl Acad Sci. 2004, 101 (13), 4390–4395
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Oberthur, M., Leimkuhler, C., and Kahne, D., A practical method for the stereoselective generation of beta-2-deoxy glycosyl phosphates. Org Lett. 2004. 6(17): p. 2873-6.
Leimkuhler Grimes Undergraduate Publications
Belardi, J. K.; Curtis, L. A.; Clareen, S. S.; Shimp, H. L.; Leimkuhler, C. E.; Simonowicz, N. L.; Casillas, E. “A Nazarov Approach to 4-Benzoyloxymethyl-cyclopent-2-enone, a Precursor to the Helminthosporols.” Synth Comm 2005, 35, 1633-1640.