Complete Publications (Graphical Abstracts)

Complete Publications (Graphical Abstracts)

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Read up on the latest publications in diversity-oriented synthesis, rational drug design, chemical biology, and drug discovery research from the Tan Lab!

Selected Publications: Text Only | Graphical Abstracts
Complete Publications: Text Only | Graphical Abstracts

Full-text versions of articles are available from the publisher with online journal subscription. PubMed Central (PMC) versions of articles are available free of charge.


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Tan Lab Publications

  1. Defining new chemical space for drug penetration into Gram-negative bacteria.
    Zhao, S.; Adamiak, J. W.; Bonifay, V.; Mehla, J.; Zgurskaya, H. I.; Tan, D. S.* Nat Chem Biol 2020, 16, 1293–1302.
    Abstract | PubMed | PMC ]
    Nature Chemical Biology 2020 graphical abstract

  2. Gram-scale preparation of the antibiotic lead compound salicyl-AMS, a potent inhibitor of bacterial salicylate adenylation enzymes.
    Kinarivala, N; Standke, L. C; Guney, T.; Cheng, J.; Naoyoshi, N.; Yasutomi, A.; Tan, D. S.* Method Enzymol. 2020, 638, 69–87.
    Abstract | PubMed | PMC ]
    Methods in Enzymology 2020 graphical abstract

  3. Total synthesis of the bacterial diisonitrile chalkophore SF2768.
    Xu, Y.; Tan, D. S.* Org. Lett. 2019, 21, 8731–8735.
    Abstract | PubMed | PMC ]
    Organic Letters 2019 graphical abstract

  4. Structural basis for adenylation and thioester bond formation in the ubiquitin E1.
    Hann, Z. S.; Ji, C.; Olsen, S. K.; Lu, X.; Lux, M. C.; Tan, D. S. *; Lima, C. D.* Proc. Natl. Acad. Sci. U.S.A. 2019, 15475–15484.
    Abstract | PubMed | PMC ] PNAS 2019 graphical abstract

    (Highlighted in Proc. Natl. Acad. Sci. USA )

  5. Small-molecule targeting of MUSASHI RNA-binding activity in acute myeloid leukemia.
    Minuesa, G.; Albanese, S. K.; Xie, W.; Kazansky, Y.; Worroll, D.; Chow, A.; Schurer, A.; Park, S. M.; Rotsides, C. Z.; Taggart, J.; Rizzi, A.; Naden, L. N.; Chou, T.; Gourkanti, S.; Cappel, D.; Passarelli, M. C.; Fairchild, L.; Adura, C.; Glickman, J. F.; Schulman, J.; Famulare, C.; Patel, M.; Eibl, J. K.; Ross, G. M.; Bhattacharya, S.; Tan, D. S.; Leslie, C. S.; Beuming, T.; Patel, D. J.; Goldgur, Y.; Chodera, J. D.; Kharas, M. G.* Nat Commun 2019, 10, 2691.
    Abstract | PubMed | PMC ] Nature Communications 2019 graphical abstract

  6. Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction.
    Lux, M. C.; Boby, M. L.; Brooks, J. L.; Tan, D. S.* Chem. Commun. 2019, 55, 7013–7016.
    Abstract | PubMed | PMC ] Chemical Communications 2019 graphical abstract

  7. Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors.
    Lux, M. C.; Standke, L. C.; Tan, D. S.* J. Antibiot. 2019, 72, 325–349.
    Abstract | PubMed | PMC ] Journal of Antibiotics 2019 graphical abstract

  8. Structure-based design, synthesis, and biological evaluation of non-acyl sulfamate inhibitors of the adenylate-forming enzyme MenE.
    Evans, C. E.; Si, Y.; Matarlo, J. S.; Yin, Y.; French, J. B.; Tonge, P. J.*; Tan, D. S.*Biochemistry 2019, 58, 1918–1930.
    Abstract | PubMed | PMC ] Biochemistry 2019 graphical abstract

  9. Kinetic analyses of the siderophore biosynthesis inhibitor salicyl-AMS and analogues as MbtA inhibitors and antimycobacterial agents.
    Bythrow, G. V.; Mohandas, P.; Guney, T.; Standke, L. C.; Germain, G. A.; Lu, X.; Ji, C.; Levendosky, K.; Chavadi, S. S.; Tan, D. S.*; Quadri, L. E. N.* Biochemistry 2018, 883–847.
    Abstract | PubMed | PMC ] Biochemistry 2019 graphical abstract

  10. Canvass: A crowd-sourced, natural-product screening library for exploring biological space.
    Kearney, S. E. et al. Verano, A. L.; Tan, D. S.; Rohde, J. M.* ACS. Cent. Sci. 2018, 4, 1727–1741.
    Abstract | PubMed | PMC ]
    ACS Cent Sci 2018 graphical abstract

  11. Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.
    Guney, T. ; Wenderski, T. A. ; Boudreau, M. W.; Tan, D. S.* Chem. Eur. J. 2018, in press.
    Abstract | PubMed |
    (Cover article in Chem. Eur. J ) Chemistry – A European Journal 2018graphical abstract

  12. Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants
    Verano, A. L.; Tan, D. S.* Chem. Sci. 2017, 8, 3687–3693.
    Abstract | PubMed | PMC ] Chemical Science 2017 graphical abstract

  13. Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery
    Verano, A. L.; Tan, D. S.* Isr. J. Chem. 2017, 57, 279–291.
    Abstract | PubMed | PMC ] Israel Journal of Chemistry 2017 graphical abstract

  14. Diastereoselective synthesis of highly substituted tetrahydrofurans by Pd-catalyzed tandem oxidative cyclization-redox relay reactions controlled by intramolecular hydrogen bonding.
    Brooks, J. L.; Xu, L.; Wiest, O.; Tan, D. S.* J. Org. Chem. 2017, 82, 57–75.
    Abstract | PubMed | PMC ] J. Org. Chem. 2017 graphical abstract

  15. Stereoselective synthesis, docking, and biological evaluation of difluoroindanediol-based MenE inhibitors as antibiotics.
    Evans, C. E.; Matarlo, J. S.; Tonge, P. J.*; Tan, D. S.* Org. Lett. 2016, 18, 6384–6387.
    Abstract | PubMed | PMC ] Org. Lett. 2016 graphical abstract

  16. Design, synthesis, and biological evaluation of α-hydroxyacyl-AMS inhibitors of amino acid adenylation enzymes.
    Davis, T. D.; Mohandas, P. ; Chiriac, M. I.; Bythrow, G. V.; Quadri, L. E. N.*; Tan, D. S.* Bioorg. Med. Chem. Lett. 2016, 21, 5340–5345.
    Abstract | PubMed | PMC ]  Bioorg. Med. Chem. Lett. 2016 graphical abstract

  17. Designed small-molecule inhibitors of the anthranilyl-CoA synthetase PqsA block quinolone biosynthesis in Pseudomonas aeruginosa.
    Ji, C.; Sharma, I.; Pratihar, I.; Hudson, L.; Maura, D.; Guney, T.; Rahme, L. G.; Pesci, E. C.; Coleman, J. P.; Tan, D. S.* ACS Chem. Biol. 2016, 11, 3061–3067.
    Abstract | PubMed | PMC ]
     ACS Chem. Biol 2016 graphical abstract

  18. Mechanism of MenE inhibition by acyl-adenylate analogues and discovery of novel antibacterial agents.
    Matarlo, J. S.; Evans, C. E.; Sharma, I.; Lavaud, L. J.; Ngo, S. C.; Shek, R.; Rajashankar, K. R.; French, J. B.; Tan, D. S.*; Tonge, P. J.* Biochemistry 2015, 54, 6514–6524.
    Abstract | PubMed | PMC ]
    Biochemistry 2015 graphical abstract

  19. Cheminformatic comparison of approved drugs from natural product versus synthetic origins.
    Stratton, C. F.; Newman, D. J.; Tan, D. S.* Bioorg. Med. Chem. Lett. 2015, 25, 4802–4807.
    Abstract | PubMed | PMC ]
    Bioorganic and Medicinal Chemistry Letters 2015 graphical abstract

  20. Principal component analysis as a tool for library design: A case study investigating natural products, brand-name drugs, natural product-like libraries, and drug-like libraries.
    Wenderski, T. A.; Stratton, C. F.; Bauer, R. A.; Kopp, F.; Tan, D. S.* Methods Mol. Biol. 2015, 1263, 225–242.
    Abstract | PubMed | PMC ]
    Methods in Molecular Biology 2015 graphical abstract

  21. General platform for systematic quantitative evaluation of small-molecule permeability in bacteria.
    Davis, T. D.; Gerry, C. J.; Tan, D. S.* ACS Chem. Biol. 2014, 9, 2535–2544.
    Abstract | PubMed | PMC ]
    ACS Chemical Biology 2014 graphical abstract

    (Highlighted in ACS Chem. Biol.)

  22. Solvent-dependent divergent functions of Sc(OTf)3 in stereoselective epoxide-opening spiroketalizations.
    Sharma, I.; Wurst, J. M.; Tan, D. S.* Org. Lett. 2014, 16, 2474–2477.
    Abstract | PubMed | PMC ]
    Organic Letters 2014 graphical abstract

  23. Pharmacokinetic and in vivo efficacy studies of the mycobactin biosynthesis inhibitor salicyl-AMS in mice.
    Lun, S.; Guo, H.; Adamson, J.; Cisar, J. S.; Davis, T. D.; Sundaramn Chavadi, S.; Warren, J. D.; Quadri, L. E. N.*; Tan, D. S.*; Bishai, W. R.* Antimicrob. Agents Chemother. 2013, 57, 5138–5140.
    Abstract | PubMed | PMC ]
    Antimicrobial Agents and Chemotherapy 2013 graphical abstract

  24. Diversifying complexity.
    Sharma, I.; Tan, D. S.* Nat. Chem. 2013, 5, 157–158.
    Abstract | PubMed  ]
    Nature Chemistry 2013 graphical abstract

  25. Biomimetic diversity-oriented synthesis of benzannulated medium rings via ring expansion.
    Bauer, R. A.; Wenderski, T. A.; Tan, D. S.* Nat. Chem. Biol. 2013, 9, 21–29.
    Abstract | PubMed | PMC ]
    Nature Chemical Biology 2013 graphical abstract

  26. Stereoselective synthesis of acortatarins A and B.
    Wurst, J. M.; Verano, A. L.; Tan, D. S.* Org. Lett. 2012, 14, 4442–4445.
    Abstract | PubMed | PMC ]
    Organic Letters 2012 graphical abstract

  27. A diversity-oriented synthesis approach to macrocycles via oxidative ring expansion.
    Kopp, F.; Stratton, C. F.; Akella, L. B.; Tan, D. S.* Nat. Chem. Biol. 2012, 8, 358–365.
    Abstract | PubMed | PMC ]
    Nature Chemical Biology 2012 graphical abstract

    (Highlighted in SciBX )

  28. Stable analogues of OSB-AMP: Potent inhibitors of MenE, the o-succinylbenzoate-CoA synthetase from bacterial menaquninone biosynthesis.
    Lu, X.; Zhou, R.; Sharma, I.; Li, X.; Kumar, G.; Swaminathan, S.; Tonge, P. J.*; Tan, D. S.* ChemBioChem 2012, 13, 129–136.
    Abstract | PubMed | PMC ]
    ChemBioChem 2012 graphical abstract

  29. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.
    Wurst, J. M.; Liu, G.; Tan, D. S.* J. Am. Chem. Soc. 2011, 133, 7916–7925.
    Abstract | PubMed | PMC ]
    Journal of the American Chemical Society 2011 graphical abstract

  30. Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library.
    Moura-Letts, G.; DiBlasi, C. M.; Bauer, R. A.; Tan, D. S.* Proc. Natl. Acad. Sci. USA 2011, 108, 6745–6750.
    Abstract | PubMed | PMC ]
    Proceedings of the National Academy of Science USA 2011 graphical abstract

  31. The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis.
    Bauer, R. A.; DiBlasi, C. M.; Tan, D. S.* Org. Lett. 2010, 12, 2084–2087.
    Abstract | PubMed | PMC ]
    Organic Letters 2010 graphical abstract

  32. Expanding the range of ’druggable’ targets with natural product-based libraries: An academic perspective.
    Bauer, R. A.; Wurst, J. M.; Tan, D. S.* Curr. Opin. Chem. Biol. 2010, 14, 308–314.
    Abstract | PubMed | PMC ]
    Current Opinion in Chemical Biology 2010 graphical abstract

  33. Active site remodelling accompanies thioester bond formation in the SUMO E1.
    Olsen, S. K.; Capili. A. D.; Lu, X.; Tan, D. S.*; Lima, C. D.* Nature 2010, 463, 906–912.
    Abstract | PubMed | PMC ]
    Nature 2010 graphical abstract

    (Highlighted in Nature, Chem. Eng. News, Nat. Rev. Mol. Cell Biol., Nat. Chem. Biol., Structure, ACS Chem. Biol., and Faculty of 1000 Biology )

  34. Designed semisynthetic protein inhibitors of Ub/Ubl E1 activating enzymes.
    Lu, X.; Olsen, S. K.; Capili, A. D.; Cisar, J. S.; Lima, C. D.*; Tan, D. S.* J. Am. Chem. Soc. 2010, 132, 1748–1749.
    Abstract | PubMed | PMC ]
    Journal of the American Chemical Society 2010 graphical abstract

    (Highlighted in Chem. Eng. News, Nat. Rev. Mol. Cell Biol., ACS Chem. Biol., and Faculty of 1000 Biology )

  35. Stereoselective synthesis of benzannulated spiroketals: Influence of the aromatic ring on reactivity and conformation.
    Liu, G.; Wurst, J. M.; Tan, D. S.* Org. Lett. 2009, 11, 3670–3673.
    Abstract | PubMed | PMC ]
    Organic Letters 2009 graphical abstract

  36. Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis.
    Lu, X.; Zhang, H.; Tonge, P. J.*; Tan, D. S.* Bioorg. Med. Chem. Lett. 2008, 18, 5963–5966.
    Abstract | PubMed | PMC ]
    Bioorganic and Medicinal Chemistry Letters 2008 graphical abstract

  37. Small molecule inhibition of microbial natural product biosynthesis – An emerging antibiotic strategy.
    Cisar, J. S.; Tan, D. S.* Chem. Soc. Rev. 2008, 37, 1320–1329.
    Abstract | PubMed | PMC ]
    Chemical Society Reviews 2008 graphical abstract

  38. Mycobacterial phenolic glycolipid virulence factor biosynthesis: Mechanism and small-molecule inhibition of polyketide chain initiation.
    Ferreras, J. A.; Stirrett, K. L.; Lu, X.; Ryu, J.-S.; Soll, C. E.; Tan, D. S.; Quadri, L. E. N.* Chem. Biol. 2008, 15, 51–61.
    Abstract | PubMed | PMC ]
    Chemical Biology 2008 graphical abstract

    (Highlighted in Chem. Biol. )

  39. Exploiting ligand conformation in selective inhibition of non-ribosomal peptide synthetase amino acid adenylation with designed macrocyclic small molecules.
    Cisar, J. S.; Ferreras, J. A.; Soni, R. K.; Quadri, L. E. N.*; Tan, D. S.* J. Am. Chem. Soc. 2007, 129, 7752–7753.
    Abstract | PubMed | PMC ]
    Journal of the American Chemical Society 2007 graphical abstract

    (Highlighted in Faculty of 1000 Biology )

  40. A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.
    Shang, S.; Iwadare, H.; Macks, D. E.; Ambrosini, L. M.; Tan, D. S.* Org. Lett. 2007, 9, 1895–1898.
    Abstract | PubMed | PMC ]
    Organic Letters 2007 graphical abstract

  41. Stereocontrolled synthesis of spiroketals via Ti(Oi-Pr)4-mediated kinetic spirocyclization of glycal epoxides with retention of configuration.
    Moilanen, S. B.; Potuzak, J. S.; Tan, D. S.* J. Am. Chem. Soc. 2006, 128, 1792–1793.
    Abstract | PubMed | PMC ]
    Jounral of the American Chemical Society 2006 graphical abstract

    (Highlighted in Nature )

  42. Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.
    Potuzak, J. S.; Moilanen, S. B.; Tan, D. S.* J. Am. Chem. Soc. 2005, 127, 13796–13797.
    Abstract | PubMed  ]
    Journal of the American Chemical Society 2005 graphical abstract

  43. Diversity-oriented synthesis: Exploring the intersections between chemistry and biology.
    Tan, D. S.* Nat. Chem. Biol. 2005, 1, 74–84.
    Abstract | PubMed ]
    Nature Chemical Biology 2005 graphical abstract

  44. Small-molecule inhibition of siderophore biosynthesis in Mycobacterium tuberculosis and Yersinia pestis.
    Ferreras, J. A.; Ryu, J.-S.; Di Lello, F.; Tan, D. S.*, Quadri, L. E. N.* Nat. Chem. Biol. 2005, 1, 29–32.
    Abstract | PubMed ]
    Nature Chemical Biology 2005 graphical abstract

    (Highlighted in Nature, Nat. Chem. Biol., Chem. Eng. News., and Mercosur Económico )

  45. Advancing chemistry and biology through diversity-oriented synthesis of natural product-like libraries.
    Shang, S.; Tan, D. S.* Curr. Opin. Chem. Biol. 2005, 9, 248–258.
    Abstract | PubMed ]
    Current Opinion in Chemical Biology 2005 graphical abstract

  46. An acid-stable tert-butyldiarylsilyl (TBDAS) linker for solid-phase organic synthesis.
    DiBlasi, C. M.; Macks, D. E.; Tan, D. S.* Org. Lett. 2005, 7, 1777–1780.
    Abstract | PubMed ]
    Organic Letters 2005 graphical abstract

    (Highlighted in Lett. Org. Chem. [PDF] )

  47. Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: New insights into glycal reactivity.
    Moilanen, S. B.; Tan, D. S.* Org. Biomol. Chem. 2005, 3, 798–803.
    Abstract | PubMed ]
    Organic and Biomolecular Chemistry 2005 graphical abstract

  48. Current progress in natural product-like libraries for discovery screening.
    Tan, D. S.* Comb. Chem. High-Throughput Screen. 2004, 7, 631–643.
    Abstract | PubMed ]
    Combinatorial Chemistry and High-Throughput Screening 2004 graphical abstract

  49. Synthesis of C1-alkyl and C1-acylglycals from glycals using a B-alkyl Suzuki–Miyaura cross coupling approach.
    Potuzak, J. S.; Tan, D. S.* Tetrahedron Lett. 2004, 45, 1797–1801.
    Abstract ]
    Tetrahedron Letters 2004 graphical abstract

  50. Discovery and applications of small molecule probes for studying biological processes.
    Potuzak, J. S.; Moilanen, S. B.; Tan, D. S.* Biotechnol. Genet. Eng. Rev. 2004, 21, 11–78.
    [PDF | PubMed ]
    Biotechnology and Genetic Engineering Reviews 2004 graphical abstract

  51. Sweet surrender to chemical genetics.
    Tan, D. S.* Nat. Biotechnol. 2002, 20, 561–563.
    Abstract | PubMed ]
    Nature Biotechnology 2002 graphical abstract


Postdoctoral Publications

  1. Total synthesis of guanacastepene A: A route to enantiomeric control.
    Mandal, M.; Yun, H.; Dudley, G. B.; Lin, S.; Tan, D. S.; Danishefsky, S. J.* J. Org. Chem. 2005, 70, 10619–10637.
    Abstract | PubMed ]
    Journal of Organic Chemistry 2005 graphical abstract

    (Featured on the Cover)

  2. Synthesis of the functionalized tricyclic skeleton of guanacastepene A: A tandem epoxide-opening β-elimination/Knoevenagel cyclization.
    Tan, D. S.; Dudley, G. B; Danishefsky, S. J.* Angew. Chem., Int. Ed. 2002, 41, 2185–2188.
    Abstract | PubMed ]
    JOURNAL YEAR graphical abstract

  3. A stereoselective route to guanacastepene A through a surprising epoxidation.
    Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J.* Angew. Chem., Int. Ed. 2002, 41, 2188–2191.
    Abstract | PubMed ]
    JOURNAL YEAR graphical abstract

  4. Remarkable stereoselectivity in the alkylation of a hydroazulenone: Progress toward the total synthesis of guanacastepene.
    Dudley, G. B.; Tan, D. S.; Kim, G.; Tanski, J. M.; Danishefsky, S. J.* Tetrahedron Lett. 2001, 42, 6789–6791.
    Abstract ]
    Tetrahedron Letters 2001 graphical abstract


Graduate Publications

  1. A mercury-catalyzed transetherification cyclization leading to fused cyclic polyethers.
    Tan, D. S.; Schreiber, S. L.* Tetrahedron Lett. 2000, 41, 9509–9513.
    Abstract ]
    Tetrahedron Letters 2000 graphical abstract

  2. Ligand discovery using encoded combinatorial libraries.
    Tan, D. S.*; Burbaum, J. J.* Curr. Opin. Drug Discovery Dev. 2000, 3, 439–453.
    [Abstract]
    Current Opinion in Drug Discovery 2000 graphical abstract

  3. Synthesis and preliminary evaluation of a library of polycyclic small molecules for use in chemical genetic assays.
    Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L.* J. Am. Chem. Soc. 1999, 121, 9073–9087.
    Abstract ]
    Journal of the American Chemical Society 1999 graphical abstract

  4. Stereoselective synthesis of over two million compounds having structural features both reminiscent of natural products and compatible with miniaturized cell-based assays.
    Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L.* J. Am. Chem. Soc. 1998, 120, 8565–8566.
    Abstract ]
    Journal of the American Chemical Society 1998 graphical abstract

    (Highlighted in Science, Chem. Eng. News. )


Undergraduate Publication

  1. Enzymatic resolution coupled with substrate racemization using a thioester substrate.
    Tan, D. S.; Günter, M. M.; Drueckhammer, D. G.* J. Am. Chem. Soc. 1995, 117, 9093–9094.
    Abstract ]
    Journal of the American Chemical Society1995 graphical abstract