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Volumn 9, Issue 1, 2018, Pages

Total synthesis and antimicrobial evaluation of natural albomycins against clinical pathogens

Author keywords

[No Author keywords available]

Indexed keywords

CIPROFLOXACIN; GRISEIN; GRISEIN DELTA 1; GRISEIN DELTA 2; GRISEIN EPSILON; NUCLEIC ACID BASE; NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; PENICILLIN G; UNCLASSIFIED DRUG; VANCOMYCIN; ANTIINFECTIVE AGENT; FERRICHROME;

EID: 85052799396     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/s41467-018-05821-1     Document Type: Article
Times cited : (72)

References (43)
  • 2
    • 85039805849 scopus 로고    scopus 로고
    • Sideromycins as pathogen-targeted antibiotics
    • Springer, Berlin, Heidelberg
    • Wencewicz, T. A. & Miller, M. J. Sideromycins as pathogen-targeted antibiotics. In Topics in Medicinal Chemistry (Springer, Berlin, Heidelberg, 2017)
    • (2017) Topics in Medicinal Chemistry
    • Wencewicz, T.A.1    Miller, M.J.2
  • 3
    • 84905299821 scopus 로고    scopus 로고
    • Siderophore-drug complexes: potential medicinal applications of the ‘Trojan horse’ strategy
    • PID: 25108321
    • Górska, A., Sloderbach, A. & Marszałł, M. P. Siderophore-drug complexes: potential medicinal applications of the ‘Trojan horse’ strategy. Trends Pharmacol. Sci. 35, 442–449 (2014)
    • (2014) Trends Pharmacol. Sci. , vol.35 , pp. 442-449
    • Górska, A.1    Sloderbach, A.2    Marszałł, M.P.3
  • 4
    • 84872850695 scopus 로고    scopus 로고
    • Siderophore conjugates
    • PID: 23346861
    • Page, M. G. P. Siderophore conjugates. Ann. N.Y. Acad. Sci. 1277, 115–126 (2013)
    • (2013) Ann. NY Acad. Sci. , vol.1277 , pp. 115-126
    • Page, M.G.P.1
  • 5
    • 77952001122 scopus 로고
    • Grisein, a new antibiotic produced by a strain of Streptomyces griseus
    • Reynolds, D. M., Schatz, A. & Waksman, S. A. Grisein, a new antibiotic produced by a strain of Streptomyces griseus. Proc. Soc. Exptl. Biol. Med. 64, 50–54 (1947)
    • (1947) Proc. Soc. Exptl. Biol. Med , vol.64 , pp. 50-54
    • Reynolds, D.M.1    Schatz, A.2    Waksman, S.A.3
  • 6
    • 84957373852 scopus 로고
    • Grisein, an antibiotic produced by certain strains of Streptomyces griseus
    • PID: 16561513
    • Reynolds, D. M. & Waksman, S. A. Grisein, an antibiotic produced by certain strains of Streptomyces griseus. J. Bacteriol. 55, 739–752 (1948)
    • (1948) J. Bacteriol. , vol.55 , pp. 739-752
    • Reynolds, D.M.1    Waksman, S.A.2
  • 7
    • 84868092065 scopus 로고
    • Iron-containing antibiotic produced by Actinomyces subtropicus
    • Braznikova, G. Iron-containing antibiotic produced by Actinomyces subtropicus. Nov. Med. 23, 3 (1951)
    • (1951) Nov. Med. , vol.23 , pp. 3
    • Braznikova, G.1
  • 8
    • 37049249675 scopus 로고
    • Penalty of isolationism
    • PID: 13409011
    • Waksman, S. A. Penalty of isolationism. Science 125, 585–587 (1957)
    • (1957) Science , vol.125 , pp. 585-587
    • Waksman, S.A.1
  • 9
    • 37049233598 scopus 로고
    • Similarity of albomycin and grisein
    • PID: 13409012
    • Stapley, E. D. & Ormond, R. E. Similarity of albomycin and grisein. Science 125, 587–589 (1957)
    • (1957) Science , vol.125 , pp. 587-589
    • Stapley, E.D.1    Ormond, R.E.2
  • 10
    • 33744725409 scopus 로고
    • Recent studies on albomycin, a new antibiotic
    • Gause, G. F. Recent studies on albomycin, a new antibiotic. Brit. Med. J. 12, 1177–1179 (1955)
    • (1955) Brit. Med. J. , vol.12 , pp. 1177-1179
    • Gause, G.F.1
  • 11
    • 34548507968 scopus 로고    scopus 로고
    • Albomycin is an effective antibiotic, as exemplified with Yersinia enterocolitica and Streptococcus pneumoniae
    • PID: 17459767
    • Pramanik, A. et al. Albomycin is an effective antibiotic, as exemplified with Yersinia enterocolitica and Streptococcus pneumoniae. Int. J. Med. Microbiol. 297, 459–469 (2007)
    • (2007) Int. J. Med. Microbiol. , vol.297 , pp. 459-469
    • Pramanik, A.1
  • 12
    • 33744744409 scopus 로고    scopus 로고
    • Albomycin uptake via a ferric hydroxamate transport system of Streptococcus pneumoniae R6
    • PID: 16707680
    • Pramanik, A. & Braun, V. Albomycin uptake via a ferric hydroxamate transport system of Streptococcus pneumoniae R6. J. Bacteriol. 188, 3878–3886 (2006)
    • (2006) J. Bacteriol. , vol.188 , pp. 3878-3886
    • Pramanik, A.1    Braun, V.2
  • 14
    • 84981886690 scopus 로고
    • Constitution of the deferriform of the albomycins δ 1 , δ 2 and ε
    • 2 and ε. Angew. Chem. Suppl. 1322−1335 (1982)
    • (1982) Angew. Chem. , pp. 1322
    • Benz, G.1
  • 16
    • 0021236248 scopus 로고
    • 5-hydroxy-L-ornithine from L-glutamic acid
    • 5-hydroxy-L-ornithine from L-glutamic acid. Liebigs. Ann. Chem. 8, 1424–1433 (1984)
    • (1984) Liebigs. Ann. Chem. , vol.8 , pp. 1424-1433
    • Benz, G.A.1
  • 18
    • 0025192584 scopus 로고
    • 5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin β-lactam conjugates: iron transport mediated drug delivery
    • PID: 2137180
    • 5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin β-lactam conjugates: iron transport mediated drug delivery. J. Med. Chem. 33, 461–464 (1990)
    • (1990) J. Med. Chem. , vol.33 , pp. 461-464
    • Dolence, E.K.1    Minnick, A.A.2    Miller, M.J.3
  • 20
    • 0033215405 scopus 로고    scopus 로고
    • Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotin-siderophore conjugate
    • Lin, Y. M. & Miller, M. J. Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotin-siderophore conjugate. J. Org. Chem. 64, 7451–7458 (1999)
    • (1999) J. Org. Chem. , vol.64 , pp. 7451-7458
    • Lin, Y.M.1    Miller, M.J.2
  • 23
    • 85052840860 scopus 로고    scopus 로고
    • 2 provides a template for assembling siderophore and aminoacyl-tRNA synthetase inhibitor conjugates
    • 2 provides a template for assembling siderophore and aminoacyl-tRNA synthetase inhibitor conjugates. Acs. Chem. Biol. 6, 1000–1007 (2012)
    • (2012) Acs. Chem. Biol. , vol.6 , pp. 1000-1007
    • Zeng, Y.1
  • 24
    • 84953896573 scopus 로고    scopus 로고
    • A branch point of Streptomyces sulfur amino acid metabolism controls the production of albomycin
    • PID: 26519385
    • Kulkarni, A. et al. A branch point of Streptomyces sulfur amino acid metabolism controls the production of albomycin. Appl. Environ. Microbiol. 82, 467–477 (2016)
    • (2016) Appl. Environ. Microbiol. , vol.82 , pp. 467-477
    • Kulkarni, A.1
  • 25
    • 70350326295 scopus 로고    scopus 로고
    • Enzymatic tailoring of ornithine in the biosynthesis of the Rhizobium cyclic trihydroxamate siderophore vicibactin
    • PID: 19778043
    • Heemstra, J. R., Walsh, C. T. & Sattely, E. S. Enzymatic tailoring of ornithine in the biosynthesis of the Rhizobium cyclic trihydroxamate siderophore vicibactin. J. Am. Chem. Soc. 131, 15317–15329 (2009)
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 15317-15329
    • Heemstra, J.R.1    Walsh, C.T.2    Sattely, E.S.3
  • 26
    • 0025326559 scopus 로고
    • 5-hydroxy-L-ornithine from L-ornithine
    • 5-hydroxy-L-ornithine from L-ornithine. Synthesis 3, 233–234 (1990)
    • (1990) Synthesis , vol.3 , pp. 233-234
    • Milewska, M.J.1    Chimiak, A.2
  • 27
    • 0027071781 scopus 로고
    • The total synthesis of nannochelin: a novel cinnamoyl hydroxamate-containing siderophore
    • Bergeron, R. J. & Phanstiel, O. I. V. The total synthesis of nannochelin: a novel cinnamoyl hydroxamate-containing siderophore. J. Org. Chem. 57, 7140–7143 (1992)
    • (1992) J. Org. Chem. , vol.57 , pp. 7140-7143
    • Bergeron, R.J.1    Phanstiel, O.I.V.2
  • 28
    • 50449088049 scopus 로고    scopus 로고
    • N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation
    • PID: 18715231
    • Katritzky, A. R., Yoshioka, M., Narindoshvili, T., Chung, A. & Khashab, N. M. N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation. Chem. Biol. Drug. Des. 72, 182–188 (2008)
    • (2008) Chem. Biol. Drug. Des. , vol.72 , pp. 182-188
    • Katritzky, A.R.1    Yoshioka, M.2    Narindoshvili, T.3    Chung, A.4    Khashab, N.M.5
  • 29
    • 14644409798 scopus 로고    scopus 로고
    • N-(Cbz- and Fmoc-α-aminoacyl)benzotriazoles: stable derivatives enabling peptide coupling of Tyr, Trp, Cys, Met, and Gln with free amino acids in aqueous media with complete retention of chirality
    • Katritzky, A. R., Angrish, P., Hür, D. & Suzuki, K. N-(Cbz- and Fmoc-α-aminoacyl)benzotriazoles: stable derivatives enabling peptide coupling of Tyr, Trp, Cys, Met, and Gln with free amino acids in aqueous media with complete retention of chirality. Synthesis 3, 397–402 (2005)
    • (2005) Synthesis , vol.3 , pp. 397-402
    • Katritzky, A.R.1    Angrish, P.2    Hür, D.3    Suzuki, K.4
  • 30
    • 33747727657 scopus 로고    scopus 로고
    • Selective peptide chain extension at the C-terminus of aspartic and glutamic acids utilizing N-protected (α-aminoacyl)benzotriazoles
    • PID: 16923025
    • Katritzky, A. R., Todadze, E., Shestopalov, A. A., Cusido, J. & Angrish, P. Selective peptide chain extension at the C-terminus of aspartic and glutamic acids utilizing N-protected (α-aminoacyl)benzotriazoles. Chem. Biol. Drug. Des. 68, 42–47 (2006)
    • (2006) Chem. Biol. Drug. Des. , vol.68 , pp. 42-47
    • Katritzky, A.R.1    Todadze, E.2    Shestopalov, A.A.3    Cusido, J.4    Angrish, P.5
  • 31
    • 64249159629 scopus 로고    scopus 로고
    • Benzotriazole-assisted solid-phase assembly of Leu-enkephalin, amyloid beta segment 34-42, and other “difficult” peptide sequences
    • PID: 19196166
    • Katritzky, A. R., Haase, D. N., Johnson, J. V. & Chung, A. Benzotriazole-assisted solid-phase assembly of Leu-enkephalin, amyloid beta segment 34-42, and other “difficult” peptide sequences. J. Org. Chem. 74, 2028–2032 (2009)
    • (2009) J. Org. Chem. , vol.74 , pp. 2028-2032
    • Katritzky, A.R.1    Haase, D.N.2    Johnson, J.V.3    Chung, A.4
  • 32
    • 33745738179 scopus 로고    scopus 로고
    • A concise, efficient and production-scale synthesis of a protected L-lyxonolactone derivative: an important aldonolactone core
    • Batra, H. et al. A concise, efficient and production-scale synthesis of a protected L-lyxonolactone derivative: an important aldonolactone core. Org. Process Res. Dev. 10, 484–486 (2006)
    • (2006) Org. Process Res. Dev. , vol.10 , pp. 484-486
    • Batra, H.1
  • 33
    • 0033588332 scopus 로고    scopus 로고
    • Nucleosides and nucleotides. 189. Investigation of the stereoselective coupling of thymine with meso-thiolane-3,4-diol-1-oxide derivatives via the Pummerer reaction
    • Naka, T., Nishizono, N., Minakawa, N. & Matsuda, A. Nucleosides and nucleotides. 189. Investigation of the stereoselective coupling of thymine with meso-thiolane-3,4-diol-1-oxide derivatives via the Pummerer reaction. Tetrahedron Lett. 40, 6297–6300 (1999)
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6297-6300
    • Naka, T.1    Nishizono, N.2    Minakawa, N.3    Matsuda, A.4
  • 34
    • 0034596301 scopus 로고    scopus 로고
    • The stereoselective synthesis of 4′-β-thioribonucleosides via the Pummerer reaction
    • Naka, T., Minakawa, N., Abe, H., Kaga, D. & Matsuda, A. The stereoselective synthesis of 4′-β-thioribonucleosides via the Pummerer reaction. J. Am. Chem. Soc. 122, 7233–7243 (2000)
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7233-7243
    • Naka, T.1    Minakawa, N.2    Abe, H.3    Kaga, D.4    Matsuda, A.5
  • 35
    • 29144461516 scopus 로고    scopus 로고
    • A practical synthesis of 4′-thioribonucleosides
    • Yoshimura, Y. et al. A practical synthesis of 4′-thioribonucleosides. Tetrahedron Lett. 47, 591–594 (2006)
    • (2006) Tetrahedron Lett. , vol.47 , pp. 591-594
    • Yoshimura, Y.1
  • 36
    • 84937757937 scopus 로고    scopus 로고
    • Synthesis of novel pyrimidine apiothionucleosides and in vitro evaluation of their cytotoxicity
    • Kotoulas, S. S., Koji, V. V., Bogdanovi, G. M. & Koumbis, A. E. Synthesis of novel pyrimidine apiothionucleosides and in vitro evaluation of their cytotoxicity. Tetrahedron 71, 3396–3403 (2015)
    • (2015) Tetrahedron , vol.71 , pp. 3396-3403
    • Kotoulas, S.S.1    Koji, V.V.2    Bogdanovi, G.M.3    Koumbis, A.E.4
  • 37
    • 33748370970 scopus 로고    scopus 로고
    • Conformational studies of 4-N-carbamoyldeoxycytidine derivatives and synthesis and hybridization properties of oligodeoxyribonucleotides incorporating these modified bases
    • Miyata, K. et al. Conformational studies of 4-N-carbamoyldeoxycytidine derivatives and synthesis and hybridization properties of oligodeoxyribonucleotides incorporating these modified bases. Eur. J. Org. Chem. 16, 3626−3637 (2006)
    • (2006) Eur. J. Org. Chem. , Issue.16 , pp. 3626-3637
    • Miyata, K.1
  • 38
    • 84869192339 scopus 로고    scopus 로고
    • Synthesis and reactivity of N-alkyl carbamoylimidazoles: development of N-methyl carbamoylimidazole as a methyl isocyanate equivalent
    • PID: 23083426
    • Duspara, P. A., Sadequl Islam, M., Lough, A. J. & Batey, R. A. Synthesis and reactivity of N-alkyl carbamoylimidazoles: development of N-methyl carbamoylimidazole as a methyl isocyanate equivalent. J. Org. Chem. 77, 10362–10368 (2012)
    • (2012) J. Org. Chem. , vol.77 , pp. 10362-10368
    • Duspara, P.A.1    Sadequl Islam, M.2    Lough, A.J.3    Batey, R.A.4
  • 39
    • 84894620752 scopus 로고    scopus 로고
    • Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters
    • PID: 24502188
    • Trost, B. M. & Miege, F. Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters. J. Am. Chem. Soc. 136, 3016–3019 (2014)
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 3016-3019
    • Trost, B.M.1    Miege, F.2
  • 40
    • 0015169332 scopus 로고
    • Antibiotics and other naturally occurring hydroxamic acids and hydroxamates
    • PID: 5004169
    • Maehr, H. Antibiotics and other naturally occurring hydroxamic acids and hydroxamates. Pure Appl. Chem. 28, 603–636 (1971)
    • (1971) Pure Appl. Chem. , vol.28 , pp. 603-636
    • Maehr, H.1
  • 41
    • 85041598079 scopus 로고    scopus 로고
    • Genome-scale analysis of Methicillin-resistant Staphylococcus aureus USA300 reveals a tradeoff between pathogenesis and drug resistance
    • PID: 29396540
    • Choe, D. et al. Genome-scale analysis of Methicillin-resistant Staphylococcus aureus USA300 reveals a tradeoff between pathogenesis and drug resistance. Sci. Rep. 8, 2215 (2018)
    • (2018) Sci. Rep. , vol.8
    • Choe, D.1
  • 42
    • 0037448618 scopus 로고    scopus 로고
    • An Escherichia coli strain, BJ5183, that shows highly efficient conservative (two-progeny) DNA double-strand break repair of restriction breaks
    • PID: 12559570
    • Takahashi, N., Yoshikura, H. & Kobayashi, I. An Escherichia coli strain, BJ5183, that shows highly efficient conservative (two-progeny) DNA double-strand break repair of restriction breaks. Gene 303, 89–97 (2003)
    • (2003) Gene , vol.303 , pp. 89-97
    • Takahashi, N.1    Yoshikura, H.2    Kobayashi, I.3
  • 43
    • 84996478385 scopus 로고    scopus 로고
    • Siderophore cephalosporin cefiderocol utilizes ferric iron transporter systems for antibacterial activity against Pseudomonas aeruginosa
    • PID: 27736756
    • Ito, A. et al. Siderophore cephalosporin cefiderocol utilizes ferric iron transporter systems for antibacterial activity against Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 60, 7396–7401 (2016)
    • (2016) Antimicrob. Agents Chemother. , vol.60 , pp. 7396-7401
    • Ito, A.1


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