Skip to main content
Log in

Stoffwechselprodukte von Mikroorganismen

Metabolic products of microorganisms

113. Mitteilung. Biosynthese von Thymidin-diphospho-mycarose durch ein zellfreies System aus Streptomyces rimosus

  • Published:
Archiv für Mikrobiologie Aims and scope Submit manuscript

Summary

A cell-free extract from mycelium of Streptomyces rimosus producing the antibiotic tylosin, catalyses the formation of TDP-mycarose from TDP-d-glucose and S-adenosyl-l-methionine. The reaction requires NADPH. The product contains a second methylated TDP-sugar with a presently unknown structure. TDP-4-Keto-6-deoxy-d-glucose is an intermediate in the reaction.

Zusammenfassung

Ein zellfreier Extrakt aus Streptomyces rimosus katalysiert die Synthese von TDP-Mycarose aus TDP-d-Glucose und S-Adenosyl-l-methionin. Die Reaktion benötigt NADPH. Das Reaktionsprodukt enthält einen weiteren methylierten TDP-Zucker unbekannter Struktur. Die Reaktion verläuft über TDP-4-Keto-6-desoxy-d-glucose als Zwischenprodukt.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literatur

  • Baddiley, J., Blumson, N. L., DiGirolamo, A., DiGirolamo, M.: Thymidine diphosphate sugar derivatives and their transformation in Streptomyces griseus. Biochim. biophys. Acta. (Amst.) 50, 391–393 (1961).

    Google Scholar 

  • Bartlett, G. R.: Phosphorous assay in column chromatography. J. biol. Chem. 234, 466–468 (1959).

    Google Scholar 

  • Blumson, N. L., Baddiley, J.: Thymidine diphosphate mannose and thymidine diphosphate, rhamnose in Streptomyces griseus. Biochem. J. 81, 114–124 (1961).

    Google Scholar 

  • Carminatti, H., Passeron, S., Dankert, M., Recondo, E.: Separation of sugar nucleotides, phosphate esters and free sugars by paper chromatography with solvents containing borates of organic bases. J. Chromatogr. 18, 342–348 (1965).

    Google Scholar 

  • Corcoran, J. W.: The biosynthesis of erythromycin. Lloydia 27, 1–14 (1964).

    Google Scholar 

  • Ferrier, R. J., Overend, W. G., Rafferty, G. A., Wall, H. M., Williams, N. R.: Determination of the configuration of branched-chain sugars. Proc. chem. Soc. 1963, 133.

  • Fischer, W., Weidemann, G.: Die Umsetzung von 2-Desoxy-d-galaktose im Stoffwechsel. II. Identifizierung der phosphorylierten Zwischenprodukte. Z. Physiol. Chem. 336, 206–218 (1964).

    Google Scholar 

  • Franz, G.: Soluble nucleotides in developing cotton hair. Phytochemistry 8, 737–741 (1969).

    Google Scholar 

  • Gilbert, J. M., Matsuhashi, M., Strominger, J. L.: Thymidine diphosphate 4-acetamido-4,6-dideoxyhexoses. II. Purification and properties of thymidine diphosphate d-glucose oxidoreductase. J. biol. Chem. 240, 1305–1308 (1965).

    Google Scholar 

  • Ginsburg, V.: Sugar nucleotides and the synthesis of carbohydrates. Advanc. Enzymol. 26, 35–88 (1964).

    Google Scholar 

  • Glaser, L., Zarkowsky, H.: Dehydration in nucleotide-linked deoxysugar synthesis. In: The enzymes, Vol. V, pp. 465–480. Ed.: P. D. Boyer. New York-London: Academic Press 1971.

    Google Scholar 

  • Grisebach, H.: Biosynthese verzweigtkettiger Zucker. Helv. chim. Acta 51, 928–939 (1968).

    Google Scholar 

  • Grisebach, H., Hofheinz, W.: Biosynthesis of macrolide, antibiotics. J. roy. Inst. Chem. 1964, 332–340.

  • Grisebach, H., Schmid, R.: Chemie und Biochemie verzweigtkettiger Zucker. Angew. Chem. 84, 192–206 (1972).

    Google Scholar 

  • Hanessian, S., Haskell, T. H.: Antibiotics containing sugars. In: The carbohydrates. Vol. IIA, pp. 139–211. Ed.: W. Pigman and D. Horton. New York-London: Academic Press 1970.

    Google Scholar 

  • Hockenhull, D. J. D.: Antibiotics. Biochemistry of industrial microorganisms, pp. 227–299. Ed.: C. Rainbow and A. H. Rose. New York-London: Academic Press 1963.

    Google Scholar 

  • Keller-Schierlein, W.: Chemie der Makrolidantibiotica. Fortschr. Chem. org. Naturst. (im Druck).

  • Krauss, M. T., Jäger, H., Schindler, O., Reichstein, T.: Papierchromatographische Differenzierung der Hexamethylosen und ihrer 3-O-Methyl-Derivate. J. Chromatogr. 3, 63–74 (1960).

    Google Scholar 

  • Larsson, A., Reichard, P.: Enzymatic reduction of ribonucleotides. Progr. Nucleic Acid Res. 7, 303–347 (1967).

    Google Scholar 

  • Lowry, O. H., Rosebrough, N. J., Farr, A. L., Randall, R. J.: Protein measurement with the Folin phenol reagent. J. biol. Chem. 193, 265–275 (1951).

    Google Scholar 

  • MacLennan, A. P., Randall, H. M., Smith, D. W.: Detection and identification of deoxysugars on paper chromatograms. Analyt. Chem. 31, 2020–2022 (1959).

    Google Scholar 

  • Martin, J. R., Goldstein, A. W.: Final steps in erythromycin biosynthesis. Progress in Antimicrobial and Anticancer Chemotherapy. Vol. II, pp. 1112–1116. Tokyo: Tokyo University Press 1970.

    Google Scholar 

  • Martin, J. R., Perun, T. J., Girolami, R. L.: Studies on the biosynthesis of erythromycins. I. Isolation and structure of an intermediate glycoside, 3-α-l-mycarosylerythronolide B. Biochemistry 5, 2852–2856 (1966).

    Google Scholar 

  • Martin, J. R., Rosenbrook, W.: Studies on the biosynthesis of erythromycins. II. Isolation and structure of a biosynthetic intermediate, 6-deoxyerythronolide B. Biochemistry 6, 435–440 (1967).

    Google Scholar 

  • Matern, H., Brillinger, G. V., Pape, H. Stoffwechselprodukte von Mikroorganismen. 114. Mitt.: Thymidin-d-glucose oxidoreduktase aus Streptomyces rimosus. Arch. Mikrobiol. 88, 37–48 (1973).

    Google Scholar 

  • Matsuhashi, M., Strominger, J. L.: Thymidine diphosphate 4-acetamido-4,6-dideoxyhexoses. J. biol. Chem. 239, 2454–2463 (1964).

    Google Scholar 

  • Matsuhashi, S., Matsuhashi, M., Strominger, J. L.: Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses. I. Over-all reactions. J. biol. Chem. 241, 4267–4274 (1966).

    Google Scholar 

  • Matsuhashi, S., Strominger, J. L.: Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses. IV. Partial resolution of the enzymes required for reduction of cytidine diphosphate 4-keto-6-deoxy-d-glucose and isolation of a new intermediate. J. biol. Chem. 242, 3494–3500 (1967).

    Google Scholar 

  • Morin, R. B., Gorman, M., Hamill, R. L., Demarco, P. V.: The structure of tylosin. Tetrahedron Letters 1970, 4737–4740.

  • Okazaki, R., Okazaki T., Strominger, J. L., Michelson, A. M.: Thymidine diphosphate 4-keto-6-deoxy-d-glucose, an intermediate in thymidine diphosphate l-rhamnose synthesis in Escherichia coli strains. J. biol. Chem. 237, 3014–3026 (1962).

    Google Scholar 

  • Okuda, S., Suzuki, N., Suzuki, S.: Isolation and structure of cytidine diphosphate 6-deoxy-3-C-methyl-2-O-methyl-l-aldohexopyranoside (cytidine diphosphate vinelose) from Azotobacter vinelandii. J. biol. Chem. 242, 958–966 (1967).

    Google Scholar 

  • Okuda, S., Suzuki, N., Suzuki, S.: Biosynthesis of branched chain sugars. IV. Isolation of cytidine diphosphate 6-deoxy-3-C-methyl-2-O-methyl-4-O-(O-methyl-glycolyl)-l-aldohexopyranoside from Azotobacter vinelandii. J. biol. Chem. 243, 6353–6360 (1968).

    Google Scholar 

  • Pape, H., Grisebach, H.: Untersuchungen über Nucleotidzucker und freie Nucleotide in S. erythreus. Biochem. Z. 343, 154–175 (1965).

    Google Scholar 

  • Pape, H., Schmid, R., Grisebach, H., Achenbach H.: Übertragung der intakten Methylgruppe des Methionins bei der Biosynthese der l-Mycarose. Europ. J. Biochem. 10, 479–483 (1969).

    Google Scholar 

  • Pape, H., Strominger, J. L.: Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses. V. Partial purification of the two protein components required for introduction of the 3-deoxy group. J. biol. Chem. 244, 3598–3604 (1969).

    Google Scholar 

  • Sandermann, H., Jr., Grisebach, H.: Biosynthesis of d-apiose. V. NAD-dependent biosynthesis of UDP-apiose and UDP-Xylose from UDP-glucuronic acid with an enzyme preparation from Lemne minor L. Biochim. biophys. Acta (Amst.) 208, 173–180 (1970).

    Google Scholar 

  • Schütte, H.-R.: Radioaktive Isotope in der Organischen Chemie und Biochemie. Weinheim: Verlag Chemie 1966.

    Google Scholar 

  • Simon, H., Floss, H. G.: Bestimmung der Isotopenverteilung in markierten Verbindungen. Berlin-Heidelberg-New York: Springer 1967.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

112. Mitteilung: T. Anke und H. Diekmann: Biosynthesis of Sideramines in Fungi. Rhodotorulic Acid Synthetase from Extracts of Rhodotorula glutinis. FEBS Letters (im Druck).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pape, H., Brillinger, G.U. Stoffwechselprodukte von Mikroorganismen. Archiv. Mikrobiol. 88, 25–35 (1973). https://doi.org/10.1007/BF00408838

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00408838

Navigation