메뉴 건너뛰기




Volumn 7, Issue 9, 2015, Pages 737-743

Use of a biosynthetic intermediate to explore the chemical diversity of pseudo-natural fungal polyketides

Author keywords

[No Author keywords available]

Indexed keywords

AZAPHILONE; BENZOPYRAN DERIVATIVE; BIOLOGICAL PRODUCT; INDOLE DERIVATIVE; PIGMENT; POLYKETIDE; POLYKETIDE SYNTHASE; QUINONE METHIDE;

EID: 84939811853     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2308     Document Type: Article
Times cited : (77)

References (42)
  • 1
    • 14944383798 scopus 로고    scopus 로고
    • The evolving role of natural products in drug discovery
    • Butler, M. S. The evolving role of natural products in drug discovery. Nature Rev. 4, 206-220 (2005).
    • (2005) Nature Rev , vol.4 , pp. 206-220
    • Butler, M.S.1
  • 2
    • 84858308226 scopus 로고    scopus 로고
    • Natural products as source of new drugs over the 30 years from 1981 to 2010
    • Newman, D. J. & Cragg, G. M. Natural products as source of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75, 311-335 (2012).
    • (2012) J. Nat. Prod , vol.75 , pp. 311-335
    • Newman, D.J.1    Cragg, G.M.2
  • 3
    • 84876002671 scopus 로고    scopus 로고
    • Natural products: A continuing source of novel drug leads
    • Cragg, G. M. & Newman, D. J. Natural products: a continuing source of novel drug leads. Biochim. Biophys. Acta 1830, 3670-3695 (2013).
    • (2013) Biochim. Biophys. Acta , vol.1830 , pp. 3670-3695
    • Cragg, G.M.1    Newman, D.J.2
  • 4
    • 2942565810 scopus 로고    scopus 로고
    • Natural products and combinatorial chemistry: Back to the future
    • Ortholand, J. Y. & Ganesan, A. Natural products and combinatorial chemistry: back to the future. Curr. Opin. Chem. Biol. 8, 271-280 (2004).
    • (2004) Curr. Opin. Chem. Biol , vol.8 , pp. 271-280
    • Ortholand, J.Y.1    Ganesan, A.2
  • 6
    • 84855809520 scopus 로고    scopus 로고
    • The interplay between mutasynthesis and semisynthesis: Generation and evaluation of an ansamitocin library
    • Eichner, S. et al. The interplay between mutasynthesis and semisynthesis: generation and evaluation of an ansamitocin library. Angew. Chem. Int. Ed. 51, 752-757 (2012).
    • (2012) Angew. Chem. Int. Ed , vol.51 , pp. 752-757
    • Eichner, S.1
  • 7
    • 84859957277 scopus 로고    scopus 로고
    • Merging chemical synthesis and biosynthesis: A new chapter in the total synthesis of natural products and natural product libraries
    • Kirschning, A. & Hahn, F. Merging chemical synthesis and biosynthesis: a new chapter in the total synthesis of natural products and natural product libraries. Angew. Chem. Int. Ed. 51, 4012-4022 (2012).
    • (2012) Angew. Chem. Int. Ed , vol.51 , pp. 4012-4022
    • Kirschning, A.1    Hahn, F.2
  • 8
    • 84863946395 scopus 로고    scopus 로고
    • The generation of 'unnatural' products: Synthetic biology meets synthetic chemistry
    • Goss, R. J. M., Shankar, S. & Fayad, A. A. The generation of 'unnatural' products: synthetic biology meets synthetic chemistry. Nat. Prod. Rep. 29, 870-889 (2012).
    • (2012) Nat. Prod. Rep , vol.29 , pp. 870-889
    • Goss, R.J.M.1    Shankar, S.2    Fayad, A.A.3
  • 9
    • 84864776550 scopus 로고    scopus 로고
    • Precursor-directed syntheses and biological evaluation of new elansolide derivatives
    • Steinmetz, H. et al. Precursor-directed syntheses and biological evaluation of new elansolide derivatives. ChemBioChem 13, 1813-1817 (2012).
    • (2012) ChemBioChem , vol.13 , pp. 1813-1817
    • Steinmetz, H.1
  • 10
    • 84887540837 scopus 로고    scopus 로고
    • Multiplexing of combinatorial chemistry in antimycin biosynthesis: Expression of molecular diversity and utility
    • Yan, Y. et al. Multiplexing of combinatorial chemistry in antimycin biosynthesis: expression of molecular diversity and utility. Angew. Chem. Int. Ed. 52, 12308-12312 (2013).
    • (2013) Angew. Chem. Int. Ed , vol.52 , pp. 12308-12312
    • Yan, Y.1
  • 11
    • 80051569814 scopus 로고    scopus 로고
    • Diversity through semisynthesis: The chemistry and biological activity of semisynthetic epothilone derivatives
    • Altmann, K. H., Gaugaz, F. Z. & Schiess, R. Diversity through semisynthesis: the chemistry and biological activity of semisynthetic epothilone derivatives. Mol. Divers. 15, 383-399 (2011).
    • (2011) Mol. Divers , vol.15 , pp. 383-399
    • Altmann, K.H.1    Gaugaz, F.Z.2    Schiess, R.3
  • 12
    • 84859367680 scopus 로고    scopus 로고
    • Synthetic diversification of natural products: Semi-synthesis and evaluation of triazole jadomycins
    • Dupuis, S. N. et al. Synthetic diversification of natural products: semi-synthesis and evaluation of triazole jadomycins. Chem. Sci. 3, 1640-1644 (2012).
    • (2012) Chem. Sci , vol.3 , pp. 1640-1644
    • Dupuis, S.N.1
  • 13
    • 84872516295 scopus 로고    scopus 로고
    • Molecular library synthesis using complex substrates: Expanding the framework of triterpenoids
    • Ignatenko, V. A., Han, Y. & Tochtrop, G. P. Molecular library synthesis using complex substrates: expanding the framework of triterpenoids. J. Org. Chem. 78, 410-418 (2013).
    • (2013) J. Org. Chem , vol.78 , pp. 410-418
    • Ignatenko, V.A.1    Han, Y.2    Tochtrop, G.P.3
  • 14
    • 82055161640 scopus 로고    scopus 로고
    • Remodeling of the natural product fumagillol employing a reaction discovery approach
    • Balthaser, B. R., Maloney, M. C., Beeler, A. B., Porco, J. A. & Snyder, J. K. Remodeling of the natural product fumagillol employing a reaction discovery approach. Nature Chem. 3, 969-973 (2011).
    • (2011) Nature Chem , vol.3 , pp. 969-973
    • Balthaser, B.R.1    Maloney, M.C.2    Beeler, A.B.3    Porco, J.A.4    Snyder, J.K.5
  • 15
    • 84875466221 scopus 로고    scopus 로고
    • A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products
    • Huigens, R. W. et al. A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products. Nature Chem. 5, 195-202 (2013).
    • (2013) Nature Chem , vol.5 , pp. 195-202
    • Huigens, R.W.1
  • 16
    • 30544434099 scopus 로고    scopus 로고
    • Fungal secondary metabolism from biochemistry to genomics
    • Keller, N. P., Turner, G. & Bennett, J. W. Fungal secondary metabolism from biochemistry to genomics. Nature Rev. Immunol. 3, 937-947 (2005).
    • (2005) Nature Rev. Immunol , vol.3 , pp. 937-947
    • Keller, N.P.1    Turner, G.2    Bennett, J.W.3
  • 17
    • 80052070698 scopus 로고    scopus 로고
    • Anticancer compounds derived from fungal endophytes: Their importance and future challenges
    • Kharwar, R. N., Mishra, A., Gond, S. K., Stierle, A. & Stierle, D. Anticancer compounds derived from fungal endophytes: their importance and future challenges. Nat. Prod. Rep. 28, 1208-1228 (2011).
    • (2011) Nat. Prod. Rep , vol.28 , pp. 1208-1228
    • Kharwar, R.N.1    Mishra, A.2    Gond, S.K.3    Stierle, A.4    Stierle, D.5
  • 18
    • 78650198931 scopus 로고    scopus 로고
    • Fungal secondary metabolites-strategies to activate silent gene clusters
    • Brakhage, A. A. & Schroeckh, V. Fungal secondary metabolites-strategies to activate silent gene clusters. Fungal Genet. Biol. 48, 15-22 (2011).
    • (2011) Fungal Genet. Biol , vol.48 , pp. 15-22
    • Brakhage, A.A.1    Schroeckh, V.2
  • 19
    • 64549150542 scopus 로고    scopus 로고
    • Triggering cryptic natural product biosynthesis in microorganisms
    • Scherlach, K. & Hertweck, C. Triggering cryptic natural product biosynthesis in microorganisms. Org. Biomol. Chem. 7, 1753-1760 (2009).
    • (2009) Org. Biomol. Chem , vol.7 , pp. 1753-1760
    • Scherlach, K.1    Hertweck, C.2
  • 20
    • 69249214114 scopus 로고    scopus 로고
    • Chemical induction of silent biosynthetic pathway transcription in Aspergillus Niger
    • Fisch, K. M. et al. Chemical induction of silent biosynthetic pathway transcription in Aspergillus niger. J. Ind. Microbiol. Biotechnol. 36, 1199-1213 (2009).
    • (2009) J. Ind. Microbiol. Biotechnol , vol.36 , pp. 1199-1213
    • Fisch, K.M.1
  • 21
    • 77955274600 scopus 로고    scopus 로고
    • SMURF: Genomic mapping of fungal secondary metabolite clusters
    • Khaldi, N. et al. SMURF: genomic mapping of fungal secondary metabolite clusters. Fungal Genet. Biol. 47, 736-741 (2010).
    • (2010) Fungal Genet. Biol , vol.47 , pp. 736-741
    • Khaldi, N.1
  • 22
    • 84873821538 scopus 로고    scopus 로고
    • Reconstitution of biosynthetic machinery for indole-diterpene paxilline in Aspergillus oryzae
    • Tagami, K. et al. Reconstitution of biosynthetic machinery for indole-diterpene paxilline in Aspergillus oryzae. J. Am. Chem. Soc. 135, 1260-1263 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 1260-1263
    • Tagami, K.1
  • 23
    • 84878214376 scopus 로고    scopus 로고
    • An efficient system for heterologous expression of secondary metabolite genes in Aspergillus nidulans
    • Chiang, Y. M. et al. An efficient system for heterologous expression of secondary metabolite genes in Aspergillus nidulans. J. Am. Chem. Soc. 135, 7720-7731 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 7720-7731
    • Chiang, Y.M.1
  • 24
    • 84880028198 scopus 로고    scopus 로고
    • Structurally diverse chaetophenol productions induced by chemically mediated epigenetic manipulation of fungal gene expression
    • Asai, T. et al. Structurally diverse chaetophenol productions induced by chemically mediated epigenetic manipulation of fungal gene expression. Org. Lett. 15, 3346-3349 (2013).
    • (2013) Org. Lett , vol.15 , pp. 3346-3349
    • Asai, T.1
  • 25
    • 84883819726 scopus 로고    scopus 로고
    • Structures of spiroindicumides A and B, unprecedented carbon skeletal spirolactones, and determination of the absolute configuration by vibrational circular dichroism exciton approach
    • Asai, T., Taniguchi, T., Yamamoto, T., Monde, K. & Oshima, Y. Structures of spiroindicumides A and B, unprecedented carbon skeletal spirolactones, and determination of the absolute configuration by vibrational circular dichroism exciton approach. Org. Lett. 15, 4320-4323 (2013).
    • (2013) Org. Lett , vol.15 , pp. 4320-4323
    • Asai, T.1    Taniguchi, T.2    Yamamoto, T.3    Monde, K.4    Oshima, Y.5
  • 26
    • 84860212543 scopus 로고    scopus 로고
    • Aromatic polyketide production in Cordyceps indigotica, an entomopathogenic fungus, induced by exposure to a histone deacetylase inhibitor
    • Asai, T., Yamamoto, T. & Oshima, Y. Aromatic polyketide production in Cordyceps indigotica, an entomopathogenic fungus, induced by exposure to a histone deacetylase inhibitor. Org. Lett. 14, 2006-2009 (2012).
    • (2012) Org. Lett , vol.14 , pp. 2006-2009
    • Asai, T.1    Yamamoto, T.2    Oshima, Y.3
  • 27
    • 84925517475 scopus 로고    scopus 로고
    • Product identification of non-reducing polyketide synthases with C-terminus methyltransferase domain from Talaromyces stipitatus using Aspergillus oryzae heterologous expression
    • Hashimoto, M. et al. Product identification of non-reducing polyketide synthases with C-terminus methyltransferase domain from Talaromyces stipitatus using Aspergillus oryzae heterologous expression. Bioorg. Med. Chem. Lett. 25, 1381-1384 (2015).
    • (2015) Bioorg. Med. Chem. Lett , vol.25 , pp. 1381-1384
    • Hashimoto, M.1
  • 28
    • 84862908298 scopus 로고    scopus 로고
    • Efficient generation of ortho-quinone methide: Application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers
    • Liao, D., Li, H. & Lei, X. Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers. Org. Lett. 14, 18-21 (2012).
    • (2012) Org. Lett , vol.14 , pp. 18-21
    • Liao, D.1    Li, H.2    Lei, X.3
  • 29
    • 0033549497 scopus 로고    scopus 로고
    • A convenient and versatile route to hydroquinolines by inter- and intramolecular aza-Diels-Alder pathways
    • Steinhagen, H. & Corey, E. J. A convenient and versatile route to hydroquinolines by inter- and intramolecular aza-Diels-Alder pathways. Angew. Chem. Int. Ed. 38, 1928-1931 (1999).
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1928-1931
    • Steinhagen, H.1    Corey, E.J.2
  • 30
    • 33746520558 scopus 로고    scopus 로고
    • Chemistry and biology of monoterpene indole alkaloid biosynthesis
    • O'Connor, S. E. & Maresh, J. J. Chemistry and biology of monoterpene indole alkaloid biosynthesis. Nat. Prod. Rep. 23, 532-547 (2006).
    • (2006) Nat. Prod. Rep , vol.23 , pp. 532-547
    • O'Connor, S.E.1    Maresh, J.J.2
  • 31
    • 84867063817 scopus 로고    scopus 로고
    • Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence
    • Xu, Z., Baunach, M., Ding, L. & Hertweck, C. Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence. Angew. Chem. Int. Ed. 51, 10293-10297 (2012).
    • (2012) Angew. Chem. Int. Ed , vol.51 , pp. 10293-10297
    • Xu, Z.1    Baunach, M.2    Ding, L.3    Hertweck, C.4
  • 32
    • 84871486514 scopus 로고    scopus 로고
    • Molecular diversity sculpted by fungal PKS-NRPS hybrids
    • Boettger, D. & Hertweck, C. Molecular diversity sculpted by fungal PKS-NRPS hybrids. ChemBioChem 14, 28-42 (2013).
    • (2013) ChemBioChem , vol.14 , pp. 28-42
    • Boettger, D.1    Hertweck, C.2
  • 33
    • 84861873661 scopus 로고    scopus 로고
    • Total synthesis of akuammiline alkaloid (-)-vincorine via intramolecular oxidative coupling
    • Zi, W., Xie, W. & Ma, D. Total synthesis of akuammiline alkaloid (-)-vincorine via intramolecular oxidative coupling. J. Am. Chem. Soc. 134, 9126-9129 (2012).
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 9126-9129
    • Zi, W.1    Xie, W.2    Ma, D.3
  • 34
    • 84901881172 scopus 로고    scopus 로고
    • Adenovirus: Current epidemiology and emerging approaches to prevention and treatment
    • Sandkovsky, U., Vargas, L. & Florescu, D. F. Adenovirus: current epidemiology and emerging approaches to prevention and treatment. Curr. Infect. Dis. Rep. 16, 416-423 (2014).
    • (2014) Curr. Infect. Dis. Rep , vol.16 , pp. 416-423
    • Sandkovsky, U.1    Vargas, L.2    Florescu, D.F.3
  • 35
    • 14744267233 scopus 로고    scopus 로고
    • Antiadenovirus activities of several classes of nucleoside and nucleotide analogues
    • Naesens, L. et al. Antiadenovirus activities of several classes of nucleoside and nucleotide analogues. Antimicrob. Agents Chemother. 49, 1010-1016 (2005).
    • (2005) Antimicrob. Agents Chemother , vol.49 , pp. 1010-1016
    • Naesens, L.1
  • 36
    • 77952564306 scopus 로고    scopus 로고
    • Human adenovirus replication in immunocompetent Syrian hamsters can be attenuated with chlorpromazine or cidofovir
    • Diaconu, I. et al. Human adenovirus replication in immunocompetent Syrian hamsters can be attenuated with chlorpromazine or cidofovir. J. Gene. Med. 12, 435-445 (2010).
    • (2010) J. Gene. Med , vol.12 , pp. 435-445
    • Diaconu, I.1
  • 37
    • 80051986672 scopus 로고    scopus 로고
    • Synthesis of unnatural alkaloid scaffolds by exploiting plant polyketide synthase
    • Morita, H. et al. Synthesis of unnatural alkaloid scaffolds by exploiting plant polyketide synthase. Proc. Natl Acad. Sci. USA 108, 13504-13509 (2013).
    • (2013) Proc. Natl Acad. Sci. USA , vol.108 , pp. 13504-13509
    • Morita, H.1
  • 38
    • 84906672709 scopus 로고    scopus 로고
    • Diversity-oriented combinatorial biosynthesis of benzenediol lactone scaffolds by subunit shuffling of fungal polyketide synthase
    • Xu, Y. et al. Diversity-oriented combinatorial biosynthesis of benzenediol lactone scaffolds by subunit shuffling of fungal polyketide synthase. Proc. Natl Acad. Sci. USA 111, 12354-12359 (2014).
    • (2014) Proc. Natl Acad. Sci. USA , vol.111 , pp. 12354-12359
    • Xu, Y.1
  • 39
    • 84881058964 scopus 로고    scopus 로고
    • Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin
    • Hansen, D. A. et al. Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin. J. Am. Chem. Soc. 135, 11232-11238 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 11232-11238
    • Hansen, D.A.1
  • 40
    • 84901036306 scopus 로고    scopus 로고
    • Systematic domain swaps of iterative, nonreducing polyketide synthases provide a mechanistic understanding and rationale for catalytic reprogramming
    • Newman, A. G., Vagstad, A. L., Storm, P. A. & Townsend, C. A. Systematic domain swaps of iterative, nonreducing polyketide synthases provide a mechanistic understanding and rationale for catalytic reprogramming. J. Am. Chem. Soc. 136, 7348-7362 (2014).
    • (2014) J. Am. Chem. Soc , vol.136 , pp. 7348-7362
    • Newman, A.G.1    Vagstad, A.L.2    Storm, P.A.3    Townsend, C.A.4
  • 41
    • 84864275239 scopus 로고    scopus 로고
    • Precursor directed biosynthesis of an orthogonally functional erythromycin analogue: Selectivity in the ribosome macrolide binding pocket
    • Harvey, C. J. B., Puglisi, J. D., Pande, V. S., Cane, D. E. & Khosla, C. Precursor directed biosynthesis of an orthogonally functional erythromycin analogue: selectivity in the ribosome macrolide binding pocket. J. Am. Chem. Soc. 134, 12259-12265 (2012).
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 12259-12265
    • Harvey, C.J.B.1    Puglisi, J.D.2    Pande, V.S.3    Cane, D.E.4    Khosla, C.5
  • 42
    • 80052078373 scopus 로고    scopus 로고
    • Engineering of an 'unnatural' natural product by swapping polyketide synthase domains in Aspergillus nidulans
    • Liu, T., Chiang, Y. M., Somoza, A. D., Oakley, B. R. & Wang, C. C. C. Engineering of an 'unnatural' natural product by swapping polyketide synthase domains in Aspergillus nidulans. J. Am. Chem. Soc. 133, 13314-13316 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 13314-13316
    • Liu, T.1    Chiang, Y.M.2    Somoza, A.D.3    Oakley, B.R.4    Wang, C.C.C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.