메뉴 건너뛰기




Volumn 9, Issue 2, 2019, Pages 433-442

Biosynthesis of clinically used antibiotic fusidic acid and identification of two short-chain dehydrogenase/reductases with converse stereoselectivity

Author keywords

Biosynthesis; Fungi; Fusidane type antibiotics; Fusidic acid; SDR

Indexed keywords

FUSIDIC ACID; SHORT CHAIN DEHYDROGENASE/REDUCTASE; SHORT CHAIN DEHYDROGENASE/REDUCTASE FUSC1; SHORT CHAIN DEHYDROGENASE/REDUCTASE FUSC2; UNCLASSIFIED DRUG;

EID: 85061093065     PISSN: 22113835     EISSN: 22113843     Source Type: Journal    
DOI: 10.1016/j.apsb.2018.10.007     Document Type: Article
Times cited : (33)

References (31)
  • 1
    • 84876760104 scopus 로고    scopus 로고
    • Protostane and fusidane triterpenes: a mini-review
    • Zhao, M., Gödecke, T., Gunn, J., Duan, J.A., Che, C.T., Protostane and fusidane triterpenes: a mini-review. Molecules 18 (2013), 4054–4080.
    • (2013) Molecules , vol.18 , pp. 4054-4080
    • Zhao, M.1    Gödecke, T.2    Gunn, J.3    Duan, J.A.4    Che, C.T.5
  • 3
    • 79955756652 scopus 로고    scopus 로고
    • In vitro antimicrobial findings for fusidic acid tested against contemporary (2008–2009) Gram-positive organisms collected in the United States
    • Jones, R.N., Mendes, R.E., Sader, H.S., Castanheira, M., In vitro antimicrobial findings for fusidic acid tested against contemporary (2008–2009) Gram-positive organisms collected in the United States. Clin Infect Dis 52 (2011), S477–S486.
    • (2011) Clin Infect Dis , vol.52 , pp. S477-S486
    • Jones, R.N.1    Mendes, R.E.2    Sader, H.S.3    Castanheira, M.4
  • 4
    • 0014687949 scopus 로고
    • Formation of the ribosome-G factor-GDP complex in the presence of fusidic acid
    • Bodley, J.W., Zieve, F.J., Lin, L., Zieve, S.T., Formation of the ribosome-G factor-GDP complex in the presence of fusidic acid. Biochem Biophys Res Commun 37 (1969), 437–443.
    • (1969) Biochem Biophys Res Commun , vol.37 , pp. 437-443
    • Bodley, J.W.1    Zieve, F.J.2    Lin, L.3    Zieve, S.T.4
  • 5
    • 84879625362 scopus 로고    scopus 로고
    • Crystal structures of EF-G-ribosome complexes trapped in intermediate states of translocation
    • Zhou, J., Lancaster, L., Donohue, J.P., Noller, H.F., Crystal structures of EF-G-ribosome complexes trapped in intermediate states of translocation. Science, 340, 2013, 1236086.
    • (2013) Science , vol.340 , pp. 1236086
    • Zhou, J.1    Lancaster, L.2    Donohue, J.P.3    Noller, H.F.4
  • 6
    • 84953213447 scopus 로고    scopus 로고
    • Fusidic acid: a bacterial elongation factor inhibitor for the oral treatment of acute and chronic Staphylococcal infections
    • Fernandes, P., Fusidic acid: a bacterial elongation factor inhibitor for the oral treatment of acute and chronic Staphylococcal infections. Cold Spring Harb Perspect Med, 6, 2016, a025437.
    • (2016) Cold Spring Harb Perspect Med , vol.6 , pp. a025437
    • Fernandes, P.1
  • 7
    • 0018618903 scopus 로고
    • Structure–activity relationships in fusidic acid-type antibiotics
    • Von Daehne, W., Godtfredsen, W.O., Rasmussen, P.R., Structure–activity relationships in fusidic acid-type antibiotics. Adv Appl Microbiol 25 (1979), 95–146.
    • (1979) Adv Appl Microbiol , vol.25 , pp. 95-146
    • Von Daehne, W.1    Godtfredsen, W.O.2    Rasmussen, P.R.3
  • 10
    • 0035855836 scopus 로고    scopus 로고
    • Synthesis and conformational analysis of fusidic acid side chain derivatives in relation to antibacterial activity
    • Duvold, T., Sørensen, M.D., Björkling, F., Henriksen, A.S., Rastrup-Andersen, N., Synthesis and conformational analysis of fusidic acid side chain derivatives in relation to antibacterial activity. J Med Chem 44 (2001), 3125–3131.
    • (2001) J Med Chem , vol.44 , pp. 3125-3131
    • Duvold, T.1    Sørensen, M.D.2    Björkling, F.3    Henriksen, A.S.4    Rastrup-Andersen, N.5
  • 11
    • 0015239456 scopus 로고
    • Mechanism of squalene cyclization. The biosynthesis of fusidic acid
    • Mulheirn, L.J., Caspi, E., Mechanism of squalene cyclization. The biosynthesis of fusidic acid. J Biol Chem 246 (1971), 2494–2501.
    • (1971) J Biol Chem , vol.246 , pp. 2494-2501
    • Mulheirn, L.J.1    Caspi, E.2
  • 12
    • 64049095850 scopus 로고    scopus 로고
    • Protostadienol biosynthesis and metabolism in the pathogenic fungus Aspergillus fumigatus
    • Lodeiro, S., Xiong, Q., Wilson, W.K., Ivanova, Y., Smith, M.L., May, G.S., et al. Protostadienol biosynthesis and metabolism in the pathogenic fungus Aspergillus fumigatus. Org Lett 11 (2009), 1241–1244.
    • (2009) Org Lett , vol.11 , pp. 1241-1244
    • Lodeiro, S.1    Xiong, Q.2    Wilson, W.K.3    Ivanova, Y.4    Smith, M.L.5    May, G.S.6
  • 13
    • 70149100848 scopus 로고    scopus 로고
    • Biosynthesis of steroidal antibiotic fusidanes: functional analysis of oxidosqualene cyclase and subsequent tailoring enzymes from Aspergillus fumigatus
    • Mitsuguchi, H., Seshime, Y., Fujii, I., Shibuya, M., Ebizuka, Y., Kushiro, T., Biosynthesis of steroidal antibiotic fusidanes: functional analysis of oxidosqualene cyclase and subsequent tailoring enzymes from Aspergillus fumigatus. J Am Chem Soc 131 (2009), 6402–6411.
    • (2009) J Am Chem Soc , vol.131 , pp. 6402-6411
    • Mitsuguchi, H.1    Seshime, Y.2    Fujii, I.3    Shibuya, M.4    Ebizuka, Y.5    Kushiro, T.6
  • 14
    • 4644219707 scopus 로고    scopus 로고
    • Development of a novel quadruple auxotrophic host transformation system by argB gene disruption using adeA gene and exploiting adenine auxotrophy in Aspergillus oryzae
    • Jin, F.J., Maruyama, J., Juvvadi, P.R., Arioka, M., Kitamoto, K., Development of a novel quadruple auxotrophic host transformation system by argB gene disruption using adeA gene and exploiting adenine auxotrophy in Aspergillus oryzae. FEMS Microbiol Lett 239 (2004), 79–85.
    • (2004) FEMS Microbiol Lett , vol.239 , pp. 79-85
    • Jin, F.J.1    Maruyama, J.2    Juvvadi, P.R.3    Arioka, M.4    Kitamoto, K.5
  • 15
    • 85034762224 scopus 로고    scopus 로고
    • Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis
    • Lv, J.M., Hu, D., Gao, H., Kushiro, T., Awakawa, T., Chen, G.D., et al. Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis. Nat Commun, 8, 2017, 1644.
    • (2017) Nat Commun , vol.8 , pp. 1644
    • Lv, J.M.1    Hu, D.2    Gao, H.3    Kushiro, T.4    Awakawa, T.5    Chen, G.D.6
  • 16
    • 85027979396 scopus 로고    scopus 로고
    • Development of a versatile and conventional technique for gene disruption in filamentous fungi based on CRISPR-Cas9 technology
    • Zheng, Y.M., Lin, F.L., Gao, H., Zou, G., Zhang, J.W., Wang, G.Q., et al. Development of a versatile and conventional technique for gene disruption in filamentous fungi based on CRISPR-Cas9 technology. Sci Rep, 7, 2017, 9250.
    • (2017) Sci Rep , vol.7 , pp. 9250
    • Zheng, Y.M.1    Lin, F.L.2    Gao, H.3    Zou, G.4    Zhang, J.W.5    Wang, G.Q.6
  • 17
    • 84872857682 scopus 로고    scopus 로고
    • New cyslabdans B and C, potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus produced by Streptomyces sp. K04-0144
    • Koyama, N., Tokura, Y., Takahashi, Y., Tomoda, H., New cyslabdans B and C, potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus produced by Streptomyces sp. K04-0144. Acta Pharm Sin B 1 (2011), 236–239.
    • (2011) Acta Pharm Sin B , vol.1 , pp. 236-239
    • Koyama, N.1    Tokura, Y.2    Takahashi, Y.3    Tomoda, H.4
  • 18
    • 84993965469 scopus 로고    scopus 로고
    • Aldgamycins J–O, 16-membered macrolides with a branched octose unit from Streptomycetes sp. and their antibacterial activities
    • Wang, C.X., Ding, R., Jiang, S.T., Tang, J.S., Hu, D., Chen, G.D., et al. Aldgamycins J–O, 16-membered macrolides with a branched octose unit from Streptomycetes sp. and their antibacterial activities. J Nat Prod 79 (2016), 2446–2454.
    • (2016) J Nat Prod , vol.79 , pp. 2446-2454
    • Wang, C.X.1    Ding, R.2    Jiang, S.T.3    Tang, J.S.4    Hu, D.5    Chen, G.D.6
  • 19
    • 85021404887 scopus 로고    scopus 로고
    • Characterization of methyltransferase AlmCII in chalcomycin biosynthesis: the first TylF family O-methyltransferase works on a 4′‐deoxysugar
    • Dai, P., Wang, C.X., Gao, H., Wang, Q.Z., Tang, X.L., Chen, G.D., et al. Characterization of methyltransferase AlmCII in chalcomycin biosynthesis: the first TylF family O-methyltransferase works on a 4′‐deoxysugar. Chembiochem 18 (2017), 1510–1517.
    • (2017) Chembiochem , vol.18 , pp. 1510-1517
    • Dai, P.1    Wang, C.X.2    Gao, H.3    Wang, Q.Z.4    Tang, X.L.5    Chen, G.D.6
  • 20
    • 0011498472 scopus 로고    scopus 로고
    • 13 C NMR spectra of some selected fusidane derivatives
    • 13 C NMR spectra of some selected fusidane derivatives. Magn Reson Chem 40 (2002), 471–473.
    • (2002) Magn Reson Chem , vol.40 , pp. 471-473
    • Rastrup-Andersen, N.1    Duvold, T.2
  • 22
    • 34047242011 scopus 로고    scopus 로고
    • Inclusion complexes of fusidic acid and three structurally related compounds with cyclodextrins
    • Larsen, K.L., Andersen, S.B., Mørkbak, A.L., Wimmer, R., Inclusion complexes of fusidic acid and three structurally related compounds with cyclodextrins. J Incl Phenom Macrocycl Chem 57 (2007), 185–190.
    • (2007) J Incl Phenom Macrocycl Chem , vol.57 , pp. 185-190
    • Larsen, K.L.1    Andersen, S.B.2    Mørkbak, A.L.3    Wimmer, R.4
  • 23
    • 84955470477 scopus 로고    scopus 로고
    • Cytochrome P450 for citreohybridonol synthesis: oxidative derivatization of the andrastin scaffold
    • Matsuda, Y., Quan, Z., Mitsuhashi, T., Li, C., Abe, I., Cytochrome P450 for citreohybridonol synthesis: oxidative derivatization of the andrastin scaffold. Org Lett 18 (2016), 296–299.
    • (2016) Org Lett , vol.18 , pp. 296-299
    • Matsuda, Y.1    Quan, Z.2    Mitsuhashi, T.3    Li, C.4    Abe, I.5
  • 24
    • 84989214558 scopus 로고    scopus 로고
    • Discovery of key dioxygenases that diverged the paraherquonin and acetoxydehydroaustin pathways in Penicillium brasilianum
    • Matsuda, Y., Iwabuchi, T., Fujimoto, T., Awakawa, T., Nakashima, Y., Mori, T., et al. Discovery of key dioxygenases that diverged the paraherquonin and acetoxydehydroaustin pathways in Penicillium brasilianum. J Am Chem Soc 138 (2016), 12671–12677.
    • (2016) J Am Chem Soc , vol.138 , pp. 12671-12677
    • Matsuda, Y.1    Iwabuchi, T.2    Fujimoto, T.3    Awakawa, T.4    Nakashima, Y.5    Mori, T.6
  • 25
    • 0037126640 scopus 로고    scopus 로고
    • Structure of bacterial 3β/17β-hydroxysteroid dehydrogenase at 1.2 Å resolution: a model for multiple steroid recognition
    • Benach, J., Filling, C., Oppermann, U.C., Roversi, P., Bricogne, G., Berndt, K.D., et al. Structure of bacterial 3β/17β-hydroxysteroid dehydrogenase at 1.2 Å resolution: a model for multiple steroid recognition. Biochemistry 41 (2002), 14659–14668.
    • (2002) Biochemistry , vol.41 , pp. 14659-14668
    • Benach, J.1    Filling, C.2    Oppermann, U.C.3    Roversi, P.4    Bricogne, G.5    Berndt, K.D.6
  • 26
    • 85030234447 scopus 로고    scopus 로고
    • Co-production of 11α-hydroxyprogesterone and ethanol using recombinant yeast expressing fungal steroid hydroxylases
    • Hull, C.M., Warrilow, A.G.S., Rolley, N.J., Price, C.L., Donnison, I.S., Kelly, D.E., et al. Co-production of 11α-hydroxyprogesterone and ethanol using recombinant yeast expressing fungal steroid hydroxylases. Biotechnol Biofuels, 10, 2017, 226.
    • (2017) Biotechnol Biofuels , vol.10 , pp. 226
    • Hull, C.M.1    Warrilow, A.G.S.2    Rolley, N.J.3    Price, C.L.4    Donnison, I.S.5    Kelly, D.E.6
  • 27
    • 78149469354 scopus 로고    scopus 로고
    • Discovery of a steroid 11α-hydroxylase from Rhizopus oryzae and its biotechnological application
    • Petrič Š., Hakki, T., Bernhardt, R., Žigon, D., Črešnar, B., Discovery of a steroid 11α-hydroxylase from Rhizopus oryzae and its biotechnological application. J Biotechnol 150 (2010), 428–437.
    • (2010) J Biotechnol , vol.150 , pp. 428-437
    • Petrič, Š.1    Hakki, T.2    Bernhardt, R.3    Žigon, D.4    Črešnar, B.5
  • 28
    • 85019094831 scopus 로고    scopus 로고
    • Cloning and identification of a novel steroid 11α-hydroxylase gene from Absidia coerulea
    • Wang, R., Sui, P., Hou, X., Cao, T., Jia, L., Lu, F., et al. Cloning and identification of a novel steroid 11α-hydroxylase gene from Absidia coerulea. J Steroid Biochem Mol Biol 171 (2017), 254–261.
    • (2017) J Steroid Biochem Mol Biol , vol.171 , pp. 254-261
    • Wang, R.1    Sui, P.2    Hou, X.3    Cao, T.4    Jia, L.5    Lu, F.6
  • 29
    • 85043375753 scopus 로고    scopus 로고
    • Biosynthesis of a ganoderic acid in Saccharomyces cerevisiae by expressing a cytochrome P450 gene from Ganoderma lucidum
    • Wang, W.F., Xiao, H., Zhong, J.J., Biosynthesis of a ganoderic acid in Saccharomyces cerevisiae by expressing a cytochrome P450 gene from Ganoderma lucidum. Biotechnol Bioeng 115 (2018), 1842–1854.
    • (2018) Biotechnol Bioeng , vol.115 , pp. 1842-1854
    • Wang, W.F.1    Xiao, H.2    Zhong, J.J.3
  • 30
    • 85046863466 scopus 로고    scopus 로고
    • Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage
    • Wang, G.Q., Chen, G.D., Qin, S.Y., Hu, D., Awakawa, T., Li, S.Y., et al. Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage. Nat Commun, 9, 2018, 1838.
    • (2018) Nat Commun , vol.9 , pp. 1838
    • Wang, G.Q.1    Chen, G.D.2    Qin, S.Y.3    Hu, D.4    Awakawa, T.5    Li, S.Y.6
  • 31
    • 33847083503 scopus 로고    scopus 로고
    • Carbonyl reductases and pluripotent hydroxysteroid dehydrogenases of the short-chain dehydrogenase/reductase superfamily
    • Hoffmann, F., Maser, E., Carbonyl reductases and pluripotent hydroxysteroid dehydrogenases of the short-chain dehydrogenase/reductase superfamily. Drug Metab Rev 39 (2007), 87–144.
    • (2007) Drug Metab Rev , vol.39 , pp. 87-144
    • Hoffmann, F.1    Maser, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.