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.
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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).
Bartlett, G. R.: Phosphorous assay in column chromatography. J. biol. Chem. 234, 466–468 (1959).
Blumson, N. L., Baddiley, J.: Thymidine diphosphate mannose and thymidine diphosphate, rhamnose in Streptomyces griseus. Biochem. J. 81, 114–124 (1961).
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).
Corcoran, J. W.: The biosynthesis of erythromycin. Lloydia 27, 1–14 (1964).
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).
Franz, G.: Soluble nucleotides in developing cotton hair. Phytochemistry 8, 737–741 (1969).
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).
Ginsburg, V.: Sugar nucleotides and the synthesis of carbohydrates. Advanc. Enzymol. 26, 35–88 (1964).
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.
Grisebach, H.: Biosynthese verzweigtkettiger Zucker. Helv. chim. Acta 51, 928–939 (1968).
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).
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.
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.
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).
Larsson, A., Reichard, P.: Enzymatic reduction of ribonucleotides. Progr. Nucleic Acid Res. 7, 303–347 (1967).
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).
MacLennan, A. P., Randall, H. M., Smith, D. W.: Detection and identification of deoxysugars on paper chromatograms. Analyt. Chem. 31, 2020–2022 (1959).
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.
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).
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).
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).
Matsuhashi, M., Strominger, J. L.: Thymidine diphosphate 4-acetamido-4,6-dideoxyhexoses. J. biol. Chem. 239, 2454–2463 (1964).
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).
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).
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).
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).
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).
Pape, H., Grisebach, H.: Untersuchungen über Nucleotidzucker und freie Nucleotide in S. erythreus. Biochem. Z. 343, 154–175 (1965).
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).
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).
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).
Schütte, H.-R.: Radioaktive Isotope in der Organischen Chemie und Biochemie. Weinheim: Verlag Chemie 1966.
Simon, H., Floss, H. G.: Bestimmung der Isotopenverteilung in markierten Verbindungen. Berlin-Heidelberg-New York: Springer 1967.
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112. Mitteilung: T. Anke und H. Diekmann: Biosynthesis of Sideramines in Fungi. Rhodotorulic Acid Synthetase from Extracts of Rhodotorula glutinis. FEBS Letters (im Druck).
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Pape, H., Brillinger, G.U. Stoffwechselprodukte von Mikroorganismen. Archiv. Mikrobiol. 88, 25–35 (1973). https://doi.org/10.1007/BF00408838
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DOI: https://doi.org/10.1007/BF00408838