Platensimycin and Platencin

Chapter 8 Platensimycin and Platencin Arun K. Ghosh, Arun K. Ghosh Purdue University, Department of Chemistry and Medicinal Chemistry, 560 Oval Drive, West Lafayette, IN, 47907-2084, USASearch for more papers by this authorKai Xi, Kai Xi Purdue University, Department of Chemistry and Medicinal Chemistry, 560 Oval Drive, West Lafayette, IN, 47907-2084, USASearch for more papers by this author Arun K. Ghosh, Arun K. Ghosh Purdue University, Department of Chemistry and Medicinal Chemistry, 560 Oval Drive, West Lafayette, IN, 47907-2084, USASearch for more papers by this authorKai Xi, Kai Xi Purdue University, Department of Chemistry and Medicinal Chemistry, 560 Oval Drive, West Lafayette, IN, 47907-2084, USASearch for more papers by this author Book Editor(s):Stephen Hanessian, Stephen Hanessian University of Montreal, Department of Chemistry, H3C 3J7 NK, CanadaSearch for more papers by this author First published: 12 February 2014 https://doi.org/10.1002/9783527676545.ch08Citations: 3Book Series:Methods and Principles in Medicinal Chemistry AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary This chapter contains sections titled: Introduction and Historical Background Discovery and Bioactivities of Platensimycin and Platencin Total and Formal Syntheses of Platensimycin Total and Formal Syntheses of Platencin Analogs of Platensimycin and Platencin Conclusions and Perspective References Bentivoglio, M. and Pacini, P. (1995) Filippo Pacini: a determined observer. Brain Research Bulletin, 38, 161–165. 10.1016/0361-9230(95)00083-Q CASPubMedWeb of Science®Google Scholar Howard-Jones, N. (1984) Robert Koch and the cholera vibrio: a centenary. British Medical Journal, 288, 379–381. 10.1136/bmj.288.6414.379 CASPubMedWeb of Science®Google Scholar Yarnel, A. (2005) Salvarsan. Chemical Engineering News, 83 (250), 116. 10.1021/cen-v083n025.p116 Google Scholar Hager, T. (2006) The Demon Under the Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug, The Crown Publishing Group. Google Scholar Diggins, F. (2003) The true history of the discovery of penicillin by Alexander Fleming. Biomedical Scientist. Institute of Biomedical Sciences, London (originally published in the Imperial College School of Medicine Gazette). Google Scholar Walsh, C. (2003) Antibiotics: Actions, Origins, Resistance, ASM Press, Washington, DC. 10.1128/9781555817886 Google Scholar Singh, S.B. and Barrett, J.F. (2006) Empirical antibacterial drug discovery – foundation in natural products. Biochemical Pharmacology, 71, 1006–1015. 10.1016/j.bcp.2005.12.016 CASPubMedWeb of Science®Google Scholar Patrick, G.L. (2001) An Introduction to Medicinal Chemistry, Oxford University Press Inc., New York. Google Scholar von Nussbaum, F., Brands, M., Hinzen, B., Weigand, S., and Häbich, D. (2006) Antibacterial natural products in medicinal chemistry – exodus or revival? Angewandte Chemie – International Edition, 45, 5072–5129. 10.1002/anie.200600350 CASPubMedWeb of Science®Google Scholar Davies, J. and Davies, D. (2010) Origins and evolution of antibiotic resistance. Microbiology and Molecular Biology Reviews, 74, 417–433. 10.1128/MMBR.00016-10 CASPubMedWeb of Science®Google Scholar Bennett, P.M. and Chopra, I. (1993) Molecular basis of β-lactamase induction in bacteria. Antimicrobial Agents and Chemotherapy, 37, 153–158. 10.1128/AAC.37.2.153 CASPubMedWeb of Science®Google Scholar Crisostomo, M.I., Westh, H., Tomasz, A., Chung, M., Oliveira, D.C., and de Lencastre, H. (2001) The evolution of methicillin resistance in Staphylococcus aureus: similarity of genetic backgrounds in historically early methicillin-susceptible and -resistant isolates and contemporary epidemic clones. Proceedings of the National Academy of Sciences of the United States of America, 98, 9865–9870. 10.1073/pnas.161272898 CASPubMedWeb of Science®Google Scholar Chambers, H.F. (2001) The changing epidemiology of Staphylococcus aureus? Emerging Infectious Diseases, 7, 178–182. 10.3201/eid0702.010204 CASPubMedWeb of Science®Google Scholar Levine, D. (2006) Vancomycin: a history. Clinical Infectious Diseases, 42, S5–S12. 10.1086/491709 CASPubMedWeb of Science®Google Scholar Barbachyn, M.R. and Ford, C.W. (2003) Oxazolidinone structure–activity relationships leading to linezolid. Angewandte Chemie – International Edition, 42, 2010–2023. 10.1002/anie.200200528 CASPubMedWeb of Science®Google Scholar Bersos, Z., Maniati, M., Kontos, F., Petinaki, E., and Maniatis, A.N. (2004) First report of a linezolid-resistant vancomycin-resistant Enterococcus faecium strain in Greece. The Journal of Antimicrobial Chemotherapy, 53, 685–686. 10.1093/jac/dkh131 CASPubMedWeb of Science®Google Scholar Moellering, R.C., Jr. (1998) Antibiotic resistance: lessons for the future. Clinical Infectious Diseases, 27, S135–S140. 10.1086/514902 CASPubMedWeb of Science®Google Scholar Koirala, K.D. and Thapa, S.D. (2011) Antibiotic resistance and the future. The Journal of the American Medical Association, 305, 2293–2294. 10.1001/jama.2011.761 CASPubMedWeb of Science®Google Scholar Wright, H.T. and Reynolds, K.A. (2007) Antibacterial targets in fatty acid biosynthesis. Current Opinion in Microbiology, 10, 447–453. 10.1016/j.mib.2007.07.001 CASPubMedWeb of Science®Google Scholar Zhang, Y.M., White, S.W., and Rock, C.O. (2006) Inhibiting bacterial fatty acid synthesis. The Journal of Biological Chemistry, 281, 17541–17544. 10.1074/jbc.R600004200 CASPubMedWeb of Science®Google Scholar Bergler, H., Fuchbichler, S., Hogenauer, G., and Turnowsky, F. (1996) The enoyl-[acyl-carrier-protein] reductase (FabI) of Escherichia coli, which catalyzes a key regulatory step in fatty acid biosynthesis, accepts NADH and NADPH as cofactors and is inhibited by palmitoyl-CoA. European Journal of Biochemistry, 242, 689–694. 10.1111/j.1432-1033.1996.0689r.x CASPubMedWeb of Science®Google Scholar Heath, R.J., Su, N., Murphy, C.K., and Rock, C.O. (2000) The enoyl-[acyl-carrier-protein] reductases FabI and FabL from Bacillus subtilis . The Journal of Biological Chemistry, 275, 40128–40133. 10.1074/jbc.M005611200 CASPubMedWeb of Science®Google Scholar Sivaraman, S., Sullivan, T.J., Johnson, F., Novichenok, P., Cui, G., Simmerling, C., and Tonge, P.J. (2004) Inhibition of the bacterial enoyl reductase FabI by triclosan: a structure–reactivity analysis of FabI inhibition by triclosan analogs. Journal of Medicinal Chemistry, 47, 509–518. 10.1021/jm030182i CASPubMedWeb of Science®Google Scholar Schulman, G.E., Choi, K.-H., Altabe, S., Rock, C.O., and de Mendoza, D. (2001) Response of Bacillus subtilis to cerulenin and acquisition of resistance. Journal of Bacteriology, 183, 3032–3040. 10.1128/JB.183.10.3032-3040.2001 PubMedWeb of Science®Google Scholar Young, K., Jayasuriya, H., Ondeyka, J.G., Herath, K., Zhang, C., Kodali, S., Galgoci, A., Painter, R., Brown-Driver, V., Yamamoto, R., Silver, L.L., Zheng, Y., Ventura, J.I., Sigmund, J., Ha, S., Basilio, A., Vicente, F., Tormo, J.R., Pelaez, F., Youngman, P., Cully, D., Barrett, J.F., Schmatz, D., Singh, S.B., and Wang, J. (2006) Discovery of FabH/FabF inhibitors from natural products. Antimicrobial Agents and Chemotherapy, 50, 519–526. 10.1128/AAC.50.2.519-526.2006 CASPubMedWeb of Science®Google Scholar Wang, J., Soisson, S.M., Young, K., Shoop, W., Kodali, S., Galgoci, A., Painter, R., Parthasarathy, G., Tang, Y.S., Cummings, R., Ha, S., Dorso, K., Motyl, M., Jayasuriya, H., Ondeyka, J., Herath, K., Zhang, C.W. et al. (2006) Platensimycin is a selective FabF inhibitor with potent antibiotic properties. Nature, 441, 358–361. 10.1038/nature04784 CASPubMedWeb of Science®Google Scholar Singh, S.B., Jayasuriya, H., Ondeyka, J.G., Herath, K.B., Zhang, C.W., Zink, D.L., Tsou, N.N., Ball, R.G., Basilio, A., Genilloud, O., Diez, M.T., Vicente, F., Pelaez, F., Young, K., and Wang, J. (2006) Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy. Journal of the American Chemical Society, 128, 11916–11920. 10.1021/ja062232p CASPubMedWeb of Science®Google Scholar Wang, J., Kodali, S., Lee, S.H., Galgoci, A., Painter, R., Dorso, K., Racine, F., Motyl, M., Hernandez, L., Tinney, E., Colletti, S.L., Herath, K. et al. (2007) Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties. Proceedings of the National Academy of Sciences of the United States of America, 104, 7612–7616. 10.1073/pnas.0700746104 CASPubMedWeb of Science®Google Scholar Jayasuriya, H., Herath, K.B., Zhang, C., Zink, D.L., Basilio, A., Genilloud, O. et al. (2007) Isolation and structure of platencin: a FabH and FabF dual inhibitor with potent broad-spectrum antibiotic activity. Angewandte Chemie –International Edition, 46, 4684–4688. 10.1002/anie.200701058 CASPubMedWeb of Science®Google Scholar Habich, D. and von Nussbaum, F. (2006) Platensimycin, a new antibiotic and “superbug challenger” from nature. ChemMedChem, 1, 951–954. 10.1002/cmdc.200600145 CASPubMedWeb of Science®Google Scholar Herath, K.B., Attygalle, A.B., and Singh, S.B. (2007) Biosynthetic studies of platensimycin. Journal of the American Chemical Society, 129, 15422–15423. 10.1021/ja0758943 CASPubMedWeb of Science®Google Scholar Herath, K., Attygalle, A.B., and Singh, S.B. (2008) Biosynthetic studies of platencin. Tetrahedron Letters, 49, 5755–5758. 10.1016/j.tetlet.2008.07.106 CASWeb of Science®Google Scholar Lu, X. and You, Q. (2010) Recent advances of platensimycin: a potential antimicrobial agent. Current Medicinal Chemistry, 17, 1139–1155. 10.2174/092986710790827852 CASPubMedWeb of Science®Google Scholar Manallack, D.T., Crosby, I.T., Khakham, Y., and Capuano, B. (2008) Platensimycin: a promising antimicrobial targeting fatty acid synthesis. Current Medicinal Chemistry, 15, 705–710. 10.2174/092986708783885255 CASPubMedWeb of Science®Google Scholar Palanichamy, K. and Kaliappan, K.P. (2010) Discovery and syntheses of “superbug challengers”– platensimycin and platencin. Chemistry – An Asian Journal, 5, 668–703. 10.1002/asia.200900423 CASPubMedWeb of Science®Google Scholar Hanessian, S., Giroux, S., and Merner, B.L. (2012) Total Synthesis from Terpenes in Design and Strategy in Organic Synthesis: From the Chiron Approach to Catalysis, Wiley-VCH Verlag GmbH, Weinheim, pp. 465–526, Chapter 13. Google Scholar Nicolaou, K.C., Li, A., and Edmonds, D.J. (2006) Total synthesis of platensimycin. Angewandte Chemie – International Edition, 45, 7086–7090. 10.1002/anie.200603892 CASPubMedWeb of Science®Google Scholar Nicolaou, K.C., Edmonds, D.J., Li, A., and Tria, G.S. (2007) Asymmetric total syntheses of platensimycin. Angewandte Chemie – International Edition, 46, 3942–3945. 10.1002/anie.200700586 CASPubMedWeb of Science®Google Scholar Ghosh, A.K. and Xi, K. (2007) Enantioselective synthesis of (−)-platensimycin oxatetracyclic core by using an intramolecular Diels–Alder reaction. Organic Letters, 9, 4013–4016. 10.1021/ol701783z CASPubMedWeb of Science®Google Scholar Ghosh, A.K. and Xi, K. (2009) Total synthesis of (−)-platensimycin, a novel antibacterial agent. The Journal of Organic Chemistry, 74, 1163–1170. 10.1021/jo802261f CASPubMedWeb of Science®Google Scholar Li, P.F., Payette, J.N., and Yamamoto, H. (2007) Enantioselective route to platensimycin: an intramolecular Robinson annulation approach. Journal of the American Chemical Society, 129, 9534–9535. 10.1021/ja073547n CASPubMedWeb of Science®Google Scholar Ishihara, K., Kurihara, H., Matsumoto, M., and Yamamoto, H. (1998) Design of Brønsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels–Alder reactions. Journal of the American Chemical Society, 120, 6920–6930. 10.1021/ja9810282 CASWeb of Science®Google Scholar Zou, Y.F., Chen, C.H., Taylor, C.D., Foxman, B.M., and Snider, B.B. (2007) Formal synthesis of (±)-platensimycin. Organic Letters, 9, 1825–1828. 10.1021/ol070563g CASPubMedWeb of Science®Google Scholar Kim, C.H., Jang, K.P., Choi, S.Y., Chung, Y.K., and Lee, E. (2008) A carbonyl ylide cycloaddition approach to platensimycin. Angewandte Chemie – International Edition, 47, 4009–4011. 10.1002/anie.200800568 CASPubMedWeb of Science®Google Scholar Lalic, G. and Corey, E.J. (2007) An effective enantioselective route to the platensimycin core. Organic Letters, 9, 4921–4923. 10.1021/ol702323s CASPubMedWeb of Science®Google Scholar Magnus, P., Rivera, H., and Lynch, V. (2010) Concise formal total synthesis of platensimycin mediated by a stereoselective autoxidation and hydroxyl group directed conjugative reduction. Organic Letters, 12, 5677–5679. 10.1021/ol102557k CASPubMedWeb of Science®Google Scholar Tiefenbacher, K., Trondlin, L., Mulzer, J., and Pfaltz, A. (2010) An expeditious asymmetric formal synthesis of the antibiotic platensimycin. Tetrahedron, 66, 6508–6513. 10.1016/j.tet.2010.04.098 CASWeb of Science®Google Scholar Nicolaou, K.C., Tria, G.S., and Edmonds, D.J. (2008) Total synthesis of platencin. Angewandte Chemie – International Edition, 47, 1780–1783. 10.1002/anie.200800066 CASPubMedWeb of Science®Google Scholar Huang, Y., Iwama, T., and Rawal, V. (2002) Design and development of highly effective Lewis acid catalysts for enantioselective Diels–Alder reactions. Journal of the American Chemical Society, 124, 5950–5951. 10.1021/ja026088t CASPubMedWeb of Science®Google Scholar Nicolaou, K.C., Toh, Q.Y., and Chen, D.Y.K. (2008) An expedient asymmetric synthesis of platencin. Journal of the American Chemical Society, 130, 11292–11293. 10.1021/ja804588r CASPubMedWeb of Science®Google Scholar Corey, E.J., Bakshi, R.K., and Shibata, S. (1987) Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. Journal of the American Chemical Society, 109, 5551–5553. 10.1021/ja00252a056 CASWeb of Science®Google Scholar Ghosh, A.K. and Xi, K. (2009) A symmetry-based concise formal synthesis of platencin, a novel lead against “superbugs”. Angewandte Chemie –International Edition, 48, 5372–5375. 10.1002/anie.200902338 CASPubMedWeb of Science®Google Scholar Hayashida, J. and Rawal, V.H. (2008) Total synthesis of (±)-platencin. Angewandte Chemie – International Edition, 47, 4373–4376. 10.1002/anie.200800756 CASPubMedWeb of Science®Google Scholar Tiefenbacher, K. and Mulzer, J. (2008) Short formal synthesis of (−)-platencin. Angewandte Chemie – International Edition, 47, 6199–6200. 10.1002/anie.200801441 PubMedGoogle Scholar Tiefenbacher, K. and Mulzer, J. (2009) A nine-step total synthesis of (−)-platencin. The Journal of Organic Chemistry, 74, 2937–2941. 10.1021/jo9001855 CASPubMedWeb of Science®Google Scholar Jayasuriya, H., Herath, K.B., Ondeyka, J.G., Zink, D.L., Burgess, B., Wang, J., and Singh, S.B. (2008) Structure of homoplatensimide A: a potential key biosynthetic intermediate of platensimycin isolated from Streptomyces platensis . Tetrahedron Letters, 49, 3648–3651. 10.1016/j.tetlet.2008.03.155 CASWeb of Science®Google Scholar Herath, K.B., Zhang, C., Jayasuriya, H., Ondeyka, J.G., Zink, D.L., Burgess, B., Wang, J., and Singh, S.B. (2008) Structure and semisynthesis of platensimide A, produced by Streptomyces platensis . Organic Letters, 10, 1699–1702. 10.1021/ol800251v CASPubMedWeb of Science®Google Scholar Zhang, C.W., Ondeyka, J., Zink, D.L., Burgess, B., Wang, J., and Singh, S.B. (2008) Isolation, structure and fatty acid synthesis inhibitory activities of platensimycin B1–B3 from Streptomyces platensis . Chemical Communications, 5034–5036. 10.1039/b810113b CASPubMedWeb of Science®Google Scholar Singh, S.B., Jayasuriya, H., Herath, K.B., Zhang, C., Ondeyka, J.G., Zink, D.L., Ha, S., Parthasarathy, G., Becker, J.W., Wang, J., and Soisson, S.M. (2009) Isolation, enzyme-bound structure, and activity of platensimycin A1 from Streptomyces platensis . Tetrahedron Letters, 50, 5182–5185. 10.1016/j.tetlet.2009.06.118 CASWeb of Science®Google Scholar Singh, S.B., Ondeyka, J.G., Herath, K.B., Zhang, C.W., Jayasuriya, H., Zink, D.L., Parthasarathy, G., Becker, J.W., Wang, J., and Soisson, S.M. (2009) Isolation, enzyme-bound structure and antibacterial activity of platencin A1 from Streptomyces platensis . Bioorganic & Medicinal Chemistry Letters, 19, 4756–4759. 10.1016/j.bmcl.2009.06.061 CASPubMedWeb of Science®Google Scholar Zhang, C.W., Ondeyka, J., Dietrich, L., Gailliot, F.P., Hesse, M., Lester, M., Dorso, K., Motyl, M., Ha, S.N., Wang, J., and Singh, S.B. (2010) Isolation, structure and biological activities of platencin A2–A4 from Streptomyces platensis . Bioorganic & Medicinal Chemistry, 18, 2602–2610. 10.1016/j.bmc.2010.02.030 CASPubMedWeb of Science®Google Scholar Nicolaou, K.C., Tang, Y.F., Wang, J.H., Stepan, A.F., Li, A., and Montero, A. (2007) Total synthesis and antibacterial properties of carbaplatensimycin. Journal of the American Chemical Society, 129, 14850–14851. 10.1021/ja076126e CASPubMedWeb of Science®Google Scholar Nicolaou, K.C., Lister, T., Denton, R.M., Montero, A., and Edmonds, D.J. (2007) Adamantaplatensimycin: a bioactive analogue of platensimycin. Angewandte Chemie – International Edition, 46, 4712–4714. 10.1002/anie.200701548 CASPubMedWeb of Science®Google Scholar Nicolaou, K.C., Stepan, A.F., Lister, T., Li, A., Montero, A., Tria, G.S., Turner, C.I., Tang, Y.F., Wang, J.H., Denton, R.M., and Edmonds, D.J. (2008) Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity. Journal of the American Chemical Society, 130, 13110–13119. 10.1021/ja8044376 CASPubMedWeb of Science®Google Scholar Jang, K.P., Kim, C.H., Na, S.W., Kim, H., Kang, H., and Lee, E. (2009) Isoplatensimycin: synthesis and biological evaluation. Bioorganic & Medicinal Chemistry Letters, 19, 4601–4602. 10.1016/j.bmcl.2009.06.092 CASPubMedWeb of Science®Google Scholar Shen, H.C., Ding, F.X., Singh, S.B., Parthasarathy, G., Soisson, S.M., Ha, S.N., Chen, X., Kodali, S., Wang, J., Dorso, K., Tata, J.R., Hammond, M.L., MacCoss, M., and Colletti, S.L. (2009) Synthesis and biological evaluation of platensimycin analogs. Bioorganic & Medicinal Chemistry Letters, 19, 1623–1627. 10.1016/j.bmcl.2009.02.006 CASPubMedWeb of Science®Google Scholar Wang, J.X. and Sintim, H.O. (2011) Dialkylamino-2,4-dihydroxybenzoic acids as easily synthesized analogues of platensimycin and platencin with comparable antibacterial properties. Chemistry – A European Journal, 17, 3352–3357. 10.1002/chem.201002410 CASPubMedWeb of Science®Google Scholar Jang, K.P., Kim, C.H., Na, S.W., Jang, D.S., Kim, H., Kang, H., and Lee, E. (2010) 7-Phenylplatensimycin and 11-methyl-7-phenylplatensimycin: more potent analogs of platensimycin. Bioorganic & Medicinal Chemistry Letters, 20, 2156–2158. 10.1016/j.bmcl.2010.02.037 CASPubMedWeb of Science®Google Scholar Barykina, O.V., Rossi, K.L., Rybak, M.J., and Snider, B.B. (2009) Synthesis and antibacterial properties of (−)-nor-platencin. Organic Letters, 11, 5334–5337. 10.1021/ol902194q CASPubMedWeb of Science®Google Scholar Tiefenbacher, K., Gollner, A., and Mulzer, J. (2010) Syntheses and antibacterial properties of iso-platencin, Cl-iso-platencin and Cl-platencin: identification of a new lead structure. Chemistry – A European Journal, 16, 9616–9622. 10.1002/chem.201000706 CASPubMedWeb of Science®Google Scholar Waalboer, D.C.J., Leenders, S., Schulin-Casonato, T., van Delft, F.L., and Rutjes, F. (2010) Total synthesis and antibiotic activity of dehydrohomoplatencin. Chemistry – A European Journal, 16, 11233–11236. 10.1002/chem.201001744 CASPubMedWeb of Science®Google Scholar Brinster, S., Lamberet, G., Staels, B., Trieu-Cuot, P., Gruss, A., and Poyart, C. (2009) Type II fatty acid synthesis is not a suitable antibiotic target for Gram-positive pathogens. Nature, 458, 83–86. 10.1038/nature07772 CASPubMedWeb of Science®Google Scholar Balemans, W., Lounis, N., Gilissen, R., Guillemont, J., Simmen, K., Andries, K., and Koul, A. (2010) Essentiality of FASII pathway for Staphylococcus aureus . Nature, 463, E3–E3. 10.1038/nature08667 CASPubMedWeb of Science®Google Scholar Brinster, S., Lamberet, G., Staels, B., Trieu-Cuot, P., Gruss, A., and Poyart, C. (2010) Brinster et al. reply. Nature, 463, E4–E4. 10.1038/nature08668 CASWeb of Science®Google Scholar Parsons, J.B., Frank, M.W., Subramanian, C., Saenkham, P., and Rock, C.O. (2011) Metabolic basis for the differential susceptibility of Gram-positive pathogens to fatty acid synthesis inhibitors. Proceedings of the National Academy of Sciences of the United States of America, 108, 15378–15383. 10.1073/pnas.1109208108 CASPubMedWeb of Science®Google Scholar Brown, A.K., Taylor, R.C., Bhatt, A., Fütterer, K., and Besra, G.S. (2009) Platensimycin activity against mycobacterial β-ketoacyl-ACP synthases. PLOS ONE, 4, e6306. 10.1371/journal.pone.0006306 CASPubMedWeb of Science®Google Scholar Wu, M., Singh, S.B., Wang, J., Chung, C.C., Salituro, G., Karanam, B.V., Lee, S.H., Powles, M., Ellsworth, K.P., Lassman, M.E., Miller, C., Myers, R.W., Tota, M.R., Zhang, B.B., and Li, C. (2011) Antidiabetic and antisteatotic effects of the selective fatty acid synthase (FAS) inhibitor platensimycin in mouse models of diabetes. Proceedings of the National Academy of Sciences of the United States of America, 108, 5378–5383. 10.1073/pnas.1002588108 CASPubMedWeb of Science®Google Scholar Citing Literature Natural Products in Medicinal Chemistry, Volume 60 ReferencesRelatedInformation

Récupéré en direct depuis OpenAlex et désinversé. Les résumés ne sont pas conservés dans cette base de données : les index inversés représentent 8,6 Go des 9,3 Go de texte de la base, et le serveur dispose de 13 Go libres.