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. 1975 Nov;8(5):526–531. doi: 10.1128/aac.8.5.526

Monophenol Monooxygenase and Lincomysin Biosynthesis in Streptomyces lincolnensis

Joanna Michalik a,1, Władysława Emilianowicz-Czerska a, Lech Switalski a, Konstancja Raczynska-Bojanowska a,1
PMCID: PMC429413  PMID: 813570

Abstract

Monophenol monooxygenase (monophenol, dihydroxyphenylalanine:oxygen oxidoreductase EC 1.14.18.1) was studied in melanin-positive and melanin-negative mutants of Streptomyces lincolnensis NCIB 9413, varying in the lincomycin synthesizing ability. The activities of laccase and tyrosine phenol lyase (EC 4.1.99.2) are absent in this organism. The monophenol monooxygenase catalyzes hydroxylation of monophenols (Km and Vmax for l-tyrosine, 2 × 10−4 M and 8.0 nmol of O2/min per ml, respectively) at a slower rate than it dehydrogenates diphenols to o-quinones (Km and Vmax for l-3,4-dihydroxyphenylalanine, 7 × 10−5 M and 51.7 nmol of O2/min per ml, respectively. It is inhibited by KCN, β-mercaptoethanol, ethylenediaminetetraacetate, dipyridyl, thiourea, p-aminobenzoic acids and by some tryptophan metabolites. Changes in the activity of monophenol monooxygenase caused by mutation or by inhibitors are reflected in the synthesis of the antibiotic. Its participation in the biogenesis of the propylhygric moiety of lincomycin is discussed.

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Selected References

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  1. ALBERTI K. G., BARTLEY W. The production of amino acids by cell fractions, particularly rat-liver mitochondria. Biochem J. 1963 Apr;87:104–114. doi: 10.1042/bj0870104. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BOUCHILLOUX S., McMAHILL P., MASON H. S. The multiple forms of mushroom tyrosinase. Purification and molecular properties of the enzymes. J Biol Chem. 1963 May;238:1699–1707. [PubMed] [Google Scholar]
  3. ESSER K. DIE PHENOLOXYDASEN DES ASCOMYCETEN PODOSPORA ANSERINA. I. DIE IDENTIFIZIERUNG VON LACCASE UND TYROSINASE BEIM WILDSTAMM. Arch Mikrobiol. 1963 Aug 1;46:217–226. [PubMed] [Google Scholar]
  4. GREGORY K. F., HUANG J. C. TYROSINASE INHERITANCE IN STREPTOMYCES SCABIES. II. INDUCTION OF TYROSINASE DEFICIENCY BY ACRIDINE DYES. J Bacteriol. 1964 Jun;87:1287–1294. doi: 10.1128/jb.87.6.1287-1294.1964. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Krasil'nikov N. A., Terekhov O. S., Zenova G. M. Vliianie stereoizomerov tirozina na obrazovanie melaninopodobnykh pigmentov aktinomitsetov. Mikrobiologiia. 1971 May-Jun;40(3):481–484. [PubMed] [Google Scholar]
  6. Kumagai H., Yamada H., Matsui H., Ohkishi H., Ogata K. Tyrosine phenol lyase. I. Purification, crystallization, and properties. J Biol Chem. 1970 Apr 10;245(7):1767–1772. [PubMed] [Google Scholar]
  7. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  8. Lapchinskaia O. A., Trenina G. A., Korobkova T. P., Nechaeva N. P., Ukholina R. S. Selektsiia aktivnykh shtammov produtsenta linkomitsina i sravnitel'noe izuchenie éffektivnosti nekotorykh mutagenov. Antibiotiki. 1968 Apr;13(4):309–316. [PubMed] [Google Scholar]
  9. Leonard T. J. Phenoloxidase activity and fruiting body formation Schizophyllum commune. J Bacteriol. 1971 Apr;106(1):162–167. doi: 10.1128/jb.106.1.162-167.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Lerch K., Ettinger L. Purification and characterization of a tyrosinase from Streptomyces glaucescens. Eur J Biochem. 1972 Dec 18;31(3):427–437. doi: 10.1111/j.1432-1033.1972.tb02549.x. [DOI] [PubMed] [Google Scholar]
  11. POMERANTZ S. H. Separation, purification, and properties of two tyrosinases from hamster melanoma. J Biol Chem. 1963 Jul;238:2351–2357. [PubMed] [Google Scholar]
  12. Robinson J., Cooper J. M. Method of determining oxygen concentrations in biological media, suitable for calibration of the oxygen electrode. Anal Biochem. 1970 Feb;33(2):390–399. doi: 10.1016/0003-2697(70)90310-6. [DOI] [PubMed] [Google Scholar]
  13. UDENFRIEND S., COOPER J. R. The chemical estimation of tyrosine and tyramine. J Biol Chem. 1952 May;196(1):227–233. [PubMed] [Google Scholar]
  14. Witz D. F., Hessler E. J., Miller T. L. Bioconversion of tyrosine into the propylhygric acid moity of lincomycin. Biochemistry. 1971 Mar 30;10(7):1128–1133. doi: 10.1021/bi00783a005. [DOI] [PubMed] [Google Scholar]

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