Publications

2014

64.        Duckworth, B. P.; Wilson, D. J.; Aldrich, C. C.* Measurement of Nonribosomal Peptide Synthetase Adenylation Domain Activity Using a Continuous Hydroxylamine Release Assay. In Methods in Molecular Biology, Nonribosomal Peptide Synthetases, vol. x, Evans, B., Ed.; Humana Press: New York, NY, USA, 2014; in press.

63.         Schiaffo, C.; Shi, C.; Xiong, Zhengmeng, Olin, M.; Aldrich, C. C.; Ferguson, D. M.* Structure Activity Relationship Analysis of Imidazoquinolines with Toll-Like Receptor 7 and 8 Selectivity and Enhanced Cytokine Induction. J. Med. Chem. 2014, 57, 339–347. DOI: 10.1021/jm4004957

62.         Xu, Z.; Yin, W.; Martinelli, L.; Evans, J.; Chen, J.; Yu, Y.; Wilson, D. J.; Mizrahi, V.; Qiao, C.*; Aldrich, C. C.* Reaction Intermediate Analogues as Bisubstrate Inhibitors of Pantothenate Synthetase. Bioorg. Med. Chem. 2014, 22, 1726–1735. DOI: 10.1016/j.bmc.2014.01.017

61.         Dai, R.; Wilson, D. J.; Geders, T. W.; Aldrich, C. C.; Finzel, B. C.* Inhibition of Mycobacterium tuberculosis Transaminase BioA by Aryl Hydrazines and Hydrazides. ChemBioChem, 2014, 15, 575–586. DOI: 10.1002/cbic.20130074

2013     

60.           Kim, J-H.; O’Brien, K. M.; Sharma, R.; Boshoff, H. I.; Rehren, G.; Chakraborty, S.; Wallach, J. B.; Monteleone, M.; Wilson, D. J.; Aldrich, C. C.; Barry, C. E.; Rhee, K.; Ehrt, S.; Schnappinger, D.* A Novel Genetic Switch Identifies the Mycobacterium tuberculosis NAD Synthetase as a Target for the Development of Improved Tuberculosis Chemotherapies. Proc. Natl. Acad. Sci USA 2013, 110, 19095–19100. DOI:10.1073/pnas.1315860110

59.         Shi, C.; Tiwari, D.; Wilson, D. J.; Seiler, C. L.; Schnappinger, D.; Aldrich, C. C.* Bisubstrate Inhibitors of Biotin Protein Ligase from Mycobacterium tuberculosis Resistant to Cyclo-Nucleoside Formation. ACS Med. Chem. Lett. 2013, 4, 1213–1217. DOI: 10.1021/ml400328a

58.         Meissner, A.; Boshoff, H. I.; Vasan, M.; Duckworth, B. P.; Barry, C. E. 3rd; Aldrich, C. C.* Structure-activitiy Relationships of 2-Aminothiazoles Effective Against Mycobacterium tuberculosis. Bioorg. Med. Chem. 2013, 21, 6385–6397. DOI: 10.1016/j.bmc.2013.08.048

57.         Engellhart, C. A.; Aldrich, C. C. Synthesis of Chromone, Quinolone, and Benzoxazinone Sulfonamide Nucleosides as Conformationally Constrained Inhibitors of Adenylating Enzymes Required for Siderophore Biosynthesis. J. Org. Chem. 2013, 78, 7470–7481. DOI: 10.1021/jo400976f

56.         Teitelbaum, A. M.; Meissner, A.; Wong, C. A.; Aldrich, C. C.*; Remmel, R. P.* Synthesis, pH-Dependent, and Plasma Stability of Meropenem Prodrugs for Drug-Resistant Tuberculosis. Bioorg. Med. Chem. 2013, 21, 5605–5617. DOI: 10.1016/j.bmc.2013.05.024

55.     Neres, J.; Engelhart, C. A.; Drake, E. J.; Wilson, D. J.; Fu, P.; Boshoff, H. I.; Barry, C. E. 3rd; Gulick, A. M.; Aldrich, C. C.* Non-nucleoside Inhibitors of BasE, An Adenylating Enzyme in the Siderophore Biosynthetic Pathway of the Opportunistic Pathogen Acinetobacter baumannii. J. Med. Chem. 2013, 56, 2385–2405. DOI: 10.1021/jm301709s

54.     Wilson, D. J.; Shi, C.; Teitelbaum, A. M.; Gulick, A. M.; Aldrich, C. C.* Characterization of AusA: A Dimodular Nonribosomal Peptide Synthetase Responsible for Production of Aureusimine Pyrazinones. Biochemistry 2013, 52, 926–937. DOI: 10.1021/bi301330q

53.     Zhang, K.; Nelson, K. M.; Bhuripanyo, K.; Grimes, K. D.; Zhao, B.; Aldrich, C. C.*; Yin, J.* Engineering the Substrate Specificity of the DhbE Adenylation Domain by Yeast Cell Surface Display Chem. Biol. 2013, 20, 92–101. DOI: 10.1016/j.chembiol.2012.10.020

2012

52.     Duckworth, B. P.; Nelson, K.; Boshoff, H. I.; Barry, C. E.3rd; Aldrich, C. C.* Development of a Selective Activity Based Probe for Adenylating Enzymes (AEs): Profiling MbtA Involved in Siderophore Biosynthesis from Mycobacterium tuberculosis. ACS Chem. Biol. 2012, 7, 1653–1658. DOI: 10.1021/cb300112x

51.     Shi, C.; Aldrich, C. C.* Synthesis of Mechanism-Based Inhibitors of the Aminotransferase BioA Involved in Biotin Biosynthesis as Potential Antibacterial Agents. J. Org. Chem. 2012, 77, 6051–6058. DOI: 10.1021/jo3008435

50.     Martinelli, L. K.; Aldrich, C. C.* Antimetabolite Poisoning of Cofactor Biosynthesis. Chem. Biol. 2012, 19, 543–544. DOI: 10.1016/j.chembiol.2012.05.004

49.     Shi, C.; Xiong, Z.; Chittepu, P.; Aldrich, C. C.; Ohlfest, J. R.; Ferguson, D. M.* Discovery of Human Toll-like Receptor 7/8-Active Imidazoquinoline Analogs with Novel Cytokine Induction. ACS Med. Chem. Lett. 2012, 3, 501–504. DOI: 10.1021/ml300079e

48.     Nelson, K. M.; Salomon, C. E.; Aldrich, C. C.* Total Synthesis and Biological Evaluation of Transvalencin Z. J. Nat. Prod. 2012, 75, 1037–1043. DOI: 10.1021/np200972s

47.     Mitchell, C. A.; Shi, C.; Aldrich, C. C.; Gulick, A. M.* The Structure of PA1221, a Non-Ribosomal Peptide Synthetase containing Adenylation and Peptidyl Carrier Protein Domains. Biochemistry 2012, 51, 3252–3263. DOI: 10.1021/bi300112e

 46.    Duckworth, B. P.; Nelson, K. M.; Aldrich, C. C.* Adenylating Enzymes in Mycobacterium tuberculosis as Drug Targets. Curr. Top. Med. Chem. 2012, 12, 766–796. DOI: 10.2174/156802612799984571

45.     Sundlov, J.; Shi, C.; Wilson, D. J.; Aldrich, C. C.; Gulick, A. M.* Structural and Functional Investigation of the Intermolecular Interaction Between the EntE Adenylation Domain and its Cognate Carrier Protein EntB. Chem. Biol. 2012, 19, 188–198. DOI: 10.1016/j.chembiol.2011.11.013

44.     Kalinda, A.; Aldrich, C. C.* Pyrazinamide: A Frontline Drug Used for Tuberculosis. Molecular Mechanism of Action Resolved after 50 Years? Chemmedchem 2012, 7, 558–560DOI: 10.1002/cmdc.201100587.

2011

43.     Duckworth, B. P.; Geders, T. W.; Tiwari, D.; Boshoff, H. I.; Sibbald, P. A.; Barry, C. E. 3rd; Schnappinger, D.; Finzel, B. C.; Aldrich, C. C.* Inhibition of Biotin Protein Ligase from Mycobacterium tuberculosis. Chem. Biol. 2011, 18, 1432–1441. DOI: 10.1016/j.chembiol.2011.08.013

42.     Shi, C.; Geders, T. W.; Park, S. W.; Wilson, D. J.; Boshoff, H. I.; Barry, C. E. 3rd; Schnappinger, D.; Finzel, B. C.; Aldrich, C. C.* Mechanism-Based Inactivation by Aromatization of the Transaminase BioA Involved in Biotin Biosynthesis in Mycobacterium tuberculosis. J. Am. Chem. Soc. 2011, 133, 18194–18201. DOI: 10.1021/ja204036t

41.     Park, S. W.; Klotzsche, M.; Wilson, D. J.; Boshoff, H. I.; Eoh, H.; Manjunatha, U.; Blumenthal, A.; Rhee, K.; Barry, C. E. 3rd; Aldrich, C. C.; Ehrt, S.*; Schnappinger, D.* Evaluating the Sensitivity of Mycobacterium tuberculosis to Biotin Deprivation Using Regulated Gene Expression. PloS Pathogens. 2011, 7, e1002264. DOI: 10.1371/journal.ppat.1002264

40.   Grimes, K. D.; Aldrich, C. C.* A High-throughput Screening Fluorescence Polarization Assay for the Fatty Acid Adenylating Enzyme FadD28 in Mycobacterium tuberculosis. Analytical Biochem. 2011, 417, 264–273. DOI: 10.1016/j.ab.2011.06.037

39.     Wilson, D. J.; Shi, C.; Duckworth, B. P.; Murtta, J. M.; Sham, Y. Y.; Thomas, D. D.; Aldrich, C. C.* A Continuous Fluorescence Displacement Assay for BioA: An Enzyme Involved in Biotin Biosynthesis. Analytical Biochem. 2011, 416, 27–38. DOI: 10.1016/j.ab.2011.05.003

38.     Duckworth, B. P.; Boshoff, H. I.; Barry, C. E. 3rd; Aldrich, C. C.* Design of a Nucleoside Inhibitor of Biotin Protein Ligase from Mycobacterium tuberculosis, In Collection Symposium Series, XIVth Symposium on Chemistry of Nucleic Acid Components, Cesky Krumlov, Czech Republic, June 5–10, 2011; Hocek, M. Ed.; Vol. 12; Academy of Sciences of the Czech Republic: Prague, 2011; pp 199–203.

2010

37.     Vasan, M.; Neres, J.; Williams, J.; Wilson, D. J.; Teitelbaum, A. M.; Remmel, R. P.; Aldrich, C. C.* Inhibitors of the Salicylate Synthase (MbtI) from Mycobacterium tuberculosis Discovered by High-Throughput Screening. Chemmedchem, 2010, 5, 2079–2087. DOI: 10.1002/cmdc.201000275

36.    Duckworth, B. P.; Aldrich, C. C.* Assigning Enzyme Function from the Metabolic Milieu. Chem. Biol. 2010, 17, 313–314. DOI: 10.1016/j.chembiol.2010.04.001

35.     Drake, E. J.; Duckworth, B. P.; Neres, J.; Aldrich, C. C.; Gulick, A. M.* Biochemical and Structural Characterization of Bisubstrate Inhibitors of BasE, the Self-Standing Non-ribosomal Peptide Synthetase Adenylate-Forming Enzyme of Acinetobactin Synthesis. Biochemistry, 2010, 49, 9292–9305. DOI: 10.1021/bi101226n

34.      Wilson, D. J.; Aldrich, C. C.* A Continuous Kinetic Assay for Adenylation Enzyme Activity and Inhibition. Analytical Biochem. 2010, 404, 56–63. DOI: 10.1016/j.ab.2010.04.033

33.     Chen, L.*; Wilson, D. J.; Xu, Y.; Aldrich, C. C.; Felczak, K.; Sham, Y. Y.; Pankiewicz, K. W. Triazole-linked Inhibitors of Inosine Monophosphate Dehydrogenase from Human and Mycobacterium tuberculosis. J. Med. Chem. 2010, 53, 4768–4778. DOI: 10.1021/jm100424m

32.     Duckworth, B. P.; Aldrich, C. C.* Development of a High-Throughput Fluorescence Polarization Assay for the Discovery of Phosphopantetheinyl Transferase Inhibitors. Analytical Biochem. 2010, 403, 13–19. DOI: 10.1016/j.ab.2010.04.009

31.    Shi, C.; Aldrich, C. C.* Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C-OH Bond Activation Using PyBroP. Org. Lett. 2010, 12, 2286–2289. DOI: 10.1021/ol100657n

30.     Sikora, A. L.; Wilson, D. J.; Aldrich, C. C.; Blanchard, J. S.* Kinetic and Inhibition Studies of Dihydroxybenzoate-AMP Ligase (EntE) from Escherichia coli. Biochemistry 2010, 49, 3648–3657. DOI: 10.1021/bi100350c

29.     Grimes, K. D.; Gupte, A.; Aldrich, C. C.* Copper(II)-Catalyzed Conversion of Aryl/Heteroaryl Boronic acids, -Boronates, and –Trifluoroboronates to the Corresponding Azides: Substrate Scope and Limitations. Synthesis 2010, 1441–1448. DOI: 10.1055/s-0029-1218683

28.     Aldrich, C. C.; Boshoff, H. I.; Remmel, R. P. Antitubercular Agents. In Burgers Medicinal Chemistry, 7th Edition; Eds. Rotella, D.; Abraham, D. J.; Wiley, 2010; 713–812.

2009

27.     Schneider, P.; Jacobs, J. M.; Neres, J.; Aldrich, C. C.; Allen, C.; Nett, M.; Hoffmeister, D.* The Global Virulence Regulators VsrAD and PhcA Control Secondary Metabolism in the Plant Pathogen Ralstonia solanacearum. Chembiochem 2009, 10, 2730–2732. DOI: 10.1002/cbic.200900510

26.     Misiek, M.; Williams, J.; Schmich, K.; Hüttel, W.; Merfort, I.; Salomon, C. E.; Aldrich, C. C.; Hoffmeister, D.* Structure and cytotoxicity of Arnamial and Related Fungal Sesquiterpene Aryl Esters. J. Nat. Prod. 2009, 72, 1888–1891. DOI: 10.1021/np900314p

25.     Petrelli, R.; Sham, Y. Y.; Chen, L.; Felczak, K.; Bennett, E.; Wilson, D. J.; Aldrich, C. C.; Yu, J. S.; Cappellacci, L.; Franchetti, P.; Grifantini, M.; Mazzola, F.; Di Stefano, M.; Magni, G.; Pankiewicz, K. W.* Selective Inhibition of NAD Kinases by Dinucleoside Disulfide NAD Mimics of NAD Analogues. Bioorg. Med. Chem. 2009, 17, 5656–5664. DOI: 10.1016/j.bmc.2009.06.013

2008

24.     Gupte, A.; Boshoff, H. I.; Wilson, D. J.; Neres, J.; Labello, N. P.; Somu, R. V.; Xing, C.; Barry, C. E. 3rd; Aldrich, C. C.* 2-Triazole Substituted Analogues of 5’-O-[N-(Salicyl)sulfamoyl]-adenosine: Antibacterial Nucleosides Effective Against Mycobacterium tuberculosis. J. Med. Chem. 2008, 51, 7495–7507. DOI: 10.1021/jm8008037

23.     Labello, N. P.; Neres, J. Bennett, E. M.; Ferguson, D. M.*; Aldrich, C. C. Quantitative Three Dimensional Structure Linear Interaction Energy Model of 5’-O-[N-(Salicyl)sulfamoyl]adenosine and the Aryl Acid Adenylating Enzyme MbtA. J. Med. Chem. 2008, 51, 7154–7160. DOI: 10.1021/jm800668u

22.     Neres, J.; Wilson, D. J.; Celia, L.; Beck, B. J.; Aldrich, C. C.* Aryl Acid Adenylating Enzymes (AAAE) Involved in Siderophore Biosynthesis: Development of a Fluorescence Polarization Assay, Determination of AAAE Ligand Specificity, and Discovery of Non-nucleoside Inhibitors. Biochemistry, 2008, 47, 11735–11749. DOI: 10.1021/bi801625b

21.     Neres, J.; Labello, N. P.; Somu, R. V.; Boshoff, H. I.; Wilson, D. J.; Vannada, J.; Chen, L.; Barry, C. E. 3rd; Bennett, E. M.; Aldrich, C. C.* Inhibition of Siderophore Biosynthesis in Mycobacterium tuberculosis with Nucleoside Bisubstrate Analogues: Structure Activity Relationships of the Nucleobase Domain of 5’-O-[N-(Salicyl)sulfamoyl]adenosine. J. Med. Chem. 2008, 51, 5349–5370. DOI: 10.1021/jm800567v

20.     Aldrich, C. C.; Somu, R. V. Nucleoside Antibiotics as Antitubercular Agents. In Nucleosides in Biochemistry, Biotechnology and Medicine; Herdewijn, P., Ed.; Wiley: Weinheim, Germany, 2008; 365–391.

19.     Gupte, A.; Subramanian, M.; Remmel, R. P.; Aldrich, C. C.* Synthesis of Deuterium-labelled 5’-O-[N-(Salicyl)sulfamoyl]adenosine (Sal-AMS-d4) as an Internal Standard for Quantitation of Sal-AMS. J. Label. Compd. Radiopharm. 2008, 51, 118–122. DOI: 10.1002/jlcr.1490

2007

18.     Qiao, C.; Gupte, A.; Boshoff, H. I.; Wilson, D. J.; Bennett, E. M.; Somu, R. V.; Barry, C. E. III.; Aldrich, C. C. * 5’-O-[(N-Acyl)sulfamoyl]adenosines as Antitubercular Agents that Inhibit MbtA: An Aryl Adenylating Enzyme Required for Siderophore Biosynthesis of the Mycobactins. J. Med. Chem. 2007, 50, 6080–6094. DOI: 10.1021/jm070905o

17.     Qiao, C.; Wilson, D. J.; Bennett, E. M.; Aldrich, C. C.* A Mechanism-Based Aryl Carrier Protein/Thiolation Domain Affinity Probe. J. Am. Chem. Soc. 2007, 129. 6350–6351. DOI: 10.1021/ja069201e

16.     Pfleger, B. F.; Lee, J. Y.; Somu, R. V.; Aldrich, C. C.; Hanna, P. C.; Sherman, D. H.* Characterization and Analysis of Early Enzymes for Petrobactin Biosynthesis in Bacillus anthracis. Biochemistry, 2007, 46, 4147–4157. DOI: 10.1021/bi6023995

15.     Lee, J. Y.; Janes, B. K.; Passalacqua, K. D.; Pfleger, B. F.; Bergman, N. H.; Liu, H.; Håkansson, K.; Somu, R. V.; Aldrich, C. C.; Cendrowski, S.; Hanna, P.; Sherman, D. H.* Biosynthetic Analysis of the Petrobactin Siderophore Pathway from Bacillus anthracis. J. Bacteriol. 2007, 189, 1698–1710. DOI:10.1128/JB.01526-06

2006

14.     Somu, R. V.; Wilson, D. J.; Bennett, E. M.; Boshoff, H. I.; Celia, L.; Beck, B. J.; Barry, C. E. 3rd; Aldrich. C. C.* Antitubercular Nucleosides that Inhibit Siderophore Biosynthesis: SAR of the Glycosyl Domain. J. Med. Chem. 2006, 49, 7623–7635. DOI: 10.1021/jm061068d

13.     Vannada, J.; Bennett, E. M.; Wilson, D. J.; Boshoff, H. I.; Barry, C. E. 3rd; Aldrich, C. C.* Design, Synthesis and Biological Evaluation of b-Ketosulfonamide Adenylation Inhibitors as Potential Antitubercular Agents. Org. Lett. 2006, 8, 4707–4711. DOI: 10.1021/ol0617289

12.     Somu, R. V.; Boshoff, H.; Qiao, C.; Bennett, E. M.; Barry, C. E. 3rd; Aldrich, C. C.* Rationally Designed Nucleoside Antibiotics That Inhibit Siderophore Biosynthesis of Mycobacterium tuberculosis. J. Med. Chem. 2006, 49, 31–34. DOI: 10.1021/jm051060o

Dr. Aldrich's Post-doctoral and Graduate work:


11.     Beck, Z. Q.; Aldrich, C. C.; Magarvey, N.; Georg, G. I.; Sherman, D. H. A Chemoenzymatic Synthesis of Cryptophycin/Arenastatin Natural Products. Biochemistry 2005, 44, 13457–13466. DOI: 10.1021/bi051140u

10.     Lakshmanan, V.; Aldrich, C. C.; Sherman, D. H.; Fecik, R. A. Formal Total Synthesis of the Polyketide Macrolactone Narbonolide. J. Org. Chem. 2005, 70, 7267–7272. DOI: 10.1021/jo050924a

9.      Aldrich, C. C.; Fecik, R. A.; Lakshmanan, V. Sherman, D. H. Chemoenzymatic Synthesis of the Polyketide Macrolactone 10-Deoxymethynolide. J. Am. Chem. Soc. 2005, 127, 8910–8911. DOI: 10.1021/ja0504340

8.      Aldrich, C. C.; Beck, B. J.; Fecik, R. A.;  Sherman, D. H. Biochemical Investigation of Pikromycin Biosynthesis Employing Native Penta- and Hexaketide Chain Elongation Intermediates. J. Am. Chem. Soc. 2005, 127, 8441–8452. DOI: 10.1021/ja042592h

7.      Nishizawa, T.; Aldrich, C. C.; Sherman, D. H. Molecular Analysis of the Rebeccamycin L-Amino Acid Oxidase from Lechevalieria aerocolonigenes ATCC 39243. J. Bacteriol. 2005, 187, 2084–2092. DOI: 10.1128/JB.187.6.2084-2092.2005

6.      Soulere, L; Aldrich C.; Daumke, O.; Gail, R.; Kissau, L.; Wittinghofer, A.; Waldmann, H. Synthesis of GTP-Derived Ras Ligands. Chembiochem 2004, 5, 1448–1453. DOI: 10.1002/cbic.200400133

5.      Beck, B. J.; Aldrich, C. C.; Fecik, R. A.; Reynolds, K. A.; Sherman, D. H. Substrate Recognition and Channeling of Monomodules from the Pikromycin Polyketide Synthase. J. Am. Chem. Soc. 2003, 125, 12551–12557. DOI: 10.1021/ja034841s

4.      Beck, B. J.; Aldrich, C. C.; Fecik, R. A.; Reynolds, K. A.; Sherman, D. H. Iterative Chain Elongation by a Pikromycin Monomodular Polyketide Synthase. J. Am. Chem. Soc. 2003, 125, 4682–4683. DOI: 10.1021/ja029974c

3.      Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J. E.; Saghatelian, A.; Mammen, J. Total Synthesis of the Calphostins: Application of Fischer Carbene Complexes and Thermodynamic Control of Atropisomers. J. Org. Chem. 2001, 66, 1297–1309. DOI: 10.1021/jo0014663

2.      Merlic, C. A.; Baur, A.; Aldrich, C. C. Acylamino Chromium Carbene Complexes: Direct Carbonyl Insertion, Formation of Münchnones and Trapping with Dipolarophiles. J. Am. Chem. Soc. 2000, 122, 7398–7399. DOI: 10.1021/ja9934753

 1.      Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J. E.; Saghatelian, A. Carbene Complexes in the Synthesis of Complex Natural Products: Total Synthesis of the Calphostins. J. Am. Chem. Soc. 2000, 122, 3224–3225. DOI: 10.1021/ja994313+