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. 1972 Sep;2(3):142–146. doi: 10.1128/aac.2.3.142

Phosphorylation of Lividomycin by Escherichia coli Carrying an R Factor

Masahito Yamaguchi 1, Tomoyuki Koshi 1, Fujio Kobayashi 1, Susumu Mitsuhashi 1
PMCID: PMC444281  PMID: 4597704

Abstract

A lividomycin-phosphorylating enzyme from a lividomycin-resistant strain of Escherichia coli carrying an R factor was partially purified by fractionation with ammonium sulfate and Sephadex G-100 column chromatography. The enzyme inactivated, in the presence of adenosine triphosphate and Mg2+, several antibiotics having a d-ribose moiety linked to 2-deoxystreptamine, i.e., lividomycin A and B, neomycin, paromomycin, and vistamycin, but did not inactivate the kanamycins, streptomycin, or the gentamicin C components. Chemical studies of the inactivated product suggested that the phosphorylated site of the inactivated lividomycin was the hydroxyl group of the d-ribose moiety.

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Selected References

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  1. Akita E., Tsuruoka T., Ezaki N., Niida T. Studies on antibiotic SF-733. A new antibiotic. II. Chemical structure of antibiotic SF-733. J Antibiot (Tokyo) 1970 Apr;23(4):173–183. doi: 10.7164/antibiotics.23.173. [DOI] [PubMed] [Google Scholar]
  2. Cooper D. J., Marigliano H. M., Yudis M. D., Traubel T. Recent developments in the chemistry of gentamicin. J Infect Dis. 1969 Apr-May;119(4):342–342. doi: 10.1093/infdis/119.4-5.342. [DOI] [PubMed] [Google Scholar]
  3. Doi O., Miyamoto M., Tanaka N., Umezawa H. Inactivation and phosphorylation of kanamycin by drug-resistant Staphylococcus aureus. Appl Microbiol. 1968 Sep;16(9):1282–1284. doi: 10.1128/am.16.9.1282-1284.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Doi O., Ogura M., Tanaka N., Umezawa H. Inactivation of kanamycin, neomycin, and streptomycin by enzymes obtained in cells of Pseudomonas aeruginoa. Appl Microbiol. 1968 Sep;16(9):1276–1281. doi: 10.1128/am.16.9.1276-1281.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Harwood J. H., Smith D. H. Resistance factor-mediated streptomycin resistance. J Bacteriol. 1969 Mar;97(3):1262–1271. doi: 10.1128/jb.97.3.1262-1271.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Kobayashi F., Nagoya T., Yoshimura Y., Kaneko K., Ogata S. I. Studies on new antibiotic lividomycins. V. In vitro and in vivo antimicrobial activity of lividomycin A. J Antibiot (Tokyo) 1972 Feb;25(2):128–136. [PubMed] [Google Scholar]
  7. Kobayashi F., Yamaguchi M., Eda J., Higashi F., Mitsuhashi S. Enzymatic inactivation of gentamicin C components by cell-free extract from Klebsiella pneumoniae. J Antibiot (Tokyo) 1971 Oct;24(10):719–721. doi: 10.7164/antibiotics.24.719. [DOI] [PubMed] [Google Scholar]
  8. Kobayashi F., Yamaguchi M., Mitsuhashi S. Activity of lividomycin against Pseudomonas aeruginosa: its inactivation by phosphorylation induced by resistant strains. Antimicrob Agents Chemother. 1972 Jan;1(1):17–21. doi: 10.1128/aac.1.1.17. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Kobayashi F., Yamaguchi M., Mitsuhashi S. Phosphorylated inactivation of aminoglycosidic antibiotics by Pseudomonas aeruginosa. Jpn J Microbiol. 1971 May;15(3):265–272. doi: 10.1111/j.1348-0421.1971.tb00578.x. [DOI] [PubMed] [Google Scholar]
  10. Kondo S., Okanishi M., Utahara R., Maeda K., Umezawa H. Isolation of kanamycin and paromamine inactivated by E. coli carrying R factor. J Antibiot (Tokyo) 1968 Jan;21(1):22–29. doi: 10.7164/antibiotics.21.22. [DOI] [PubMed] [Google Scholar]
  11. Mitsuhashi S., Kobayashi F., Yamaguchi M. Enzymatic inactivation of gentamicin C components by cell-free extract from Pseudomonas aeruginosa. J Antibiot (Tokyo) 1971 Jun;24(6):400–401. doi: 10.7164/antibiotics.24.400. [DOI] [PubMed] [Google Scholar]
  12. Mori T., Kyotani Y., Watanabe I., Oda T. Chemical conversion of lividomycin A into lividomycin B. J Antibiot (Tokyo) 1972 Feb;25(2):149–150. doi: 10.7164/antibiotics.25.149. [DOI] [PubMed] [Google Scholar]
  13. Naganawa H., Yagisawa M., Kondo S., Takeuchi T., Umezawa H. The structure determination of an enzymatic inactivation product of 3',4'-dideoxykanamycin B. J Antibiot (Tokyo) 1971 Dec;24(12):913–914. doi: 10.7164/antibiotics.24.913. [DOI] [PubMed] [Google Scholar]
  14. Oda T., Mori T., Kyotani Y., Nakayama M. Studies on new antibiotic lividomycins. IV. Structure of lividomycin A. J Antibiot (Tokyo) 1971 Aug;24(8):511–518. doi: 10.7164/antibiotics.24.511. [DOI] [PubMed] [Google Scholar]
  15. Oda T., Mori T., Kyotani Y. Studies on new antibiotic lividomycins. 3. Partial structure of lividomycin A. J Antibiot (Tokyo) 1971 Aug;24(8):503–510. doi: 10.7164/antibiotics.24.503. [DOI] [PubMed] [Google Scholar]
  16. Okamoto S., Suzuki Y. Chloramphenicol-, dihydrostreptomycin-, and kanamycin-inactivating enzymes from multiple drug-resistant Escherichia coli carrying episome 'R'. Nature. 1965 Dec 25;208(5017):1301–1303. doi: 10.1038/2081301a0. [DOI] [PubMed] [Google Scholar]
  17. Ozanne B., Benveniste R., Tipper D., Davies J. Aminoglycoside antibiotics: inactivation by phosphorylation in Escherichia coli carrying R factors. J Bacteriol. 1969 Nov;100(2):1144–1146. doi: 10.1128/jb.100.2.1144-1146.1969. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Umezawa H., Doi O., Ogura M., Kondo S., Tanaka N. Phosphorylation and inactivation of kanamycin by Pseudomonas aeruginosa. J Antibiot (Tokyo) 1968 Feb;21(2):154–155. doi: 10.7164/antibiotics.21.154. [DOI] [PubMed] [Google Scholar]
  19. Umezawa H., Okanishi M., Utahara R., Maeda K., Kondo S. Isolation and structure of kanamycin inactivated by a cell free system of kanamycin-resistant E. coli. J Antibiot (Tokyo) 1967 Jul;20(3):136–141. [PubMed] [Google Scholar]
  20. Umezawa H., Takasawa S., Okanishi M., Utahara R. Adenylylstreptomycin, a product of streptomycin inactivated by E. coli carrying R factor. J Antibiot (Tokyo) 1968 Jan;21(1):81–82. doi: 10.7164/antibiotics.21.81. [DOI] [PubMed] [Google Scholar]
  21. Umezawa H., Umezawa S., Tsuchiya T., Okazaki Y. 3',4'-dideoxy-kanamycin B active against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosa. J Antibiot (Tokyo) 1971 Jul;24(7):485–487. doi: 10.7164/antibiotics.24.485. [DOI] [PubMed] [Google Scholar]
  22. Yamaguchi M., Kobayashi F., Mitsuhashi S. Antibacterial activity of lividomycin toward R factor-resistant strains of Escherichia coli. Antimicrob Agents Chemother. 1972 Feb;1(2):139–142. doi: 10.1128/aac.1.2.139. [DOI] [PMC free article] [PubMed] [Google Scholar]

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