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Bacterial carotenoids

L. Absolute configuration of zeaxanthin dirhamnoside

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Abstract

Zeaxanthin dirhamnoside is the major carotenoid of Corynebacterium autotrophicum. The absolute configuration 3R,3′R followed from CD-properties of its hexaacetate, α-L-assignment and 1C4 conformation were concluded from 1H NMR data by comparison with model compounds.

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References

  • Andreesen, M., Schlegel, H. G.: A new coryneform hydrogen bacterium: Corynebacterium autotrophicum strain 7C. II. Isolation of a slime-free mutant. Arch. Microbiol. 100, 351–361 (1974)

    Google Scholar 

  • Andrewes A. G., Borch, G., Liaaen-Jensen, S., Snatzke, G.: Animal Carotenoids. 9. On the absolute configuration of astaxanthin and actinoerythrin. Acta chim. scand. B 28, 730–736 (1974a)

    Google Scholar 

  • Andrewes, A. G., Liaaen-Jensen, S., Borch, G.: Bacterial carotenoids. XLIII. C50-Carotenoids. 13. Synthesis of (2R,2′R)-2,2′-dimethyl-β,β-carotene and absolute configuration of (2R, 2′R)-2-(4-hydroxymethyl-2-butenyl)-2′-(3-methyl-2-butenyl)-β,β-carotene. Acta chem. scand. B 28, 734–742 (1974b)

    Google Scholar 

  • Arpin, N., Fiasson, J.-L., Liaaen-Jensen, S.: Bacterial carotenoids. XXXIX. C50-Carotenoids. 10. Bacterioruberin mono- and diglucoside. Acta chem. scand. 26, 2526–2528 (1972b)

    Google Scholar 

  • Arpin, N., Liaaen-Jensen, S., Trouilloud, M.: Bacterial carotenoids. XXXVIII. C50-Carotenoids. 9. Isolation of decaprenoxanthin mono- and diglucoside from an Arthrobacter sp. Acta chem. scand. 26, 2524–2526 (1972a)

    Google Scholar 

  • Arpin, N., Norgard, S., Francis, G. W., Liaaen-Jensen, S.: Bacterial carotenoids. XLI. C50-Carotenoids. II. C45- and C50-Carotenoids from Sarcina lutea-sarcinaxanthin. Acta chem. scand. 27, 2321–2334 (1973)

    Google Scholar 

  • Baumgarten, J., Reh, M., Schlegel, H. G.: Taxonomic studies of some gram-positive coryneform hydrogen bacteria. Arch. Microbiol. 100, 207–217 (1974)

    Google Scholar 

  • Borch, G., Norgård, S., Liaaen-Jensen, S.: C50-Carotenoids. 8. Circular dichroism and relative configuration of C50-carotenoids. Acta chem. scand. 25, 402–403 (1971)

    Google Scholar 

  • Claes, H.: Energieübertragung von angeregtem Chlorophyll auf C40-Polyene mit verschiedenen chromophoren Gruppen. Z. Naturforsch. 16b, 445–454 (1961)

    Google Scholar 

  • Dundas, I. D., Larsen, H.: A study on the killing by light of photosensitized cells of Halobacterium salinarium. Arch. Mikrobiol. 46, 19–28 (1963)

    Google Scholar 

  • Eimbjellen, K. E., Liaaen-Jensen, S.: The biosynthesis of carotenoids in Rhodopseudomonas galatinosa. Biochim. biophys. Acta (Amst.) 82, 21–40 (1964)

    Google Scholar 

  • Gogotov, J. N., Schlegel, H. G.: N2-Fixation by chemoautotrophic hydrogen bacteria. Arch. Microbiol. 97, 359–362 (1974)

    Google Scholar 

  • Griffiths, M., Sistrom, W. R., Cohen-Bazire G. Stanier, R. Y.: Function of carotenoids in photosynthesis. Nature (Lond.) 176, 1211–1215 (1955)

    Google Scholar 

  • Griffiths, M., Stanier, R. Y.: Some mutational changes in the photosynthetic pigment system of Rhodopseudomonas spheroides. J. gen. Microbiol. 14, 698–715 (1956)

    Google Scholar 

  • Hemmer, E., Liaaen-Jensen, S.: Spectroscopic properties of methyl-triacetyl-α-and β-L-rhamnosides. Acta chem. scand. 24, 3019–3023 (1970)

    Google Scholar 

  • Hertzberg, S., Liaaen-Jensen, S.: Absolute configuration of zeaxanthin dirhamnosides; structures of sarcinaxanthin and its glucosides. Abstr. 4th Int. IUPAC Symp. Carot., Berne, pp. 18–19 (1975)

  • IUPAC-IUB Nomenclature of carotenoids, rules approved 1974. Pure appl. Chem. (in press, 1976)

  • Johansen, J. E., Liaaen-Jensen, S.: Bacterial carotenoids. LI. C50-Carotenoids. 17. Total synthesis of two bacterioruberin derivatives. Absolute configuration of bacterioruberin. Tetrahydron Letters, pp. 995–998 (1976)

  • Kelly, M., Norgård, S., Liaaen-Jensen, S.: Bacterial carotenoids. XXXI. C50-Carotenoids. 5. Carotenoids of Halobacterium salinarium, especially bacterioruberin. Acta chem. scand. 24, 2169–2182 (1970)

    Google Scholar 

  • Killean, R. C. G., Lawrence, J. L., Sharma, V. C.: The refinement of the crystal structure of α-rhamnose monohydrate. Acta Crystallogr. B 27, 1707–1710 (1971)

    Google Scholar 

  • Kjøsen, H., Liaaen-Jensen, S.: Carotenoids of higher plants. 6. Total synthesis of lycoxanthin and lycophyll. Acta chem. scand. 26, 4121–4129 (1972)

    Google Scholar 

  • Kleinig, H., Reichenbach, H., Achenbach, H.: Carotenoid pigments of Stigmatella aurantiaca (Myxobacterales). II. Acetylated carotenoid glucosides. Arch. Mikrobiol. 74, 223–234 (1970)

    Google Scholar 

  • Krinsky, N.I.: Function. In: Carotenoids (O. Isler, ed.), pp. 670–716. Basel: Birkhäuser 1971

    Google Scholar 

  • Kunisawa, R., Stanier, R. Y.: Studies on the role of carotenoid pigments in a chemoheterotrophic bacterium, Corynebacterium poinsettiae. Arch Mikrobiol. 31, 146–156 (1958)

    Google Scholar 

  • Liaaen-Jensen, S.: The constitution of some bacterial carotenoids and their bearing on biosynthetic problems. Kgl. Norske Vit. Selsk. Skrifter 1962, No. 8, 199 pp.

  • Liaaen-Jensen, S.: Chemistry of cellular components: Carotenoids. In: Photosynthetic bacteria (R. K. Clayton, W. R. Sistrom, eds.), New York: Plenum Press 1976 (in press)

    Google Scholar 

  • Liaaen-Jensen, S., Cohen-Bazire, G., Nakayama, T. O. M., Stanier, R. Y.: The path of carotenoid synthesis in a photosynthetic bacterium. Biochim. biophys. Acta (Amst.) 29, 477–498 (1958)

    Google Scholar 

  • Liaaen-Jensen, S., Cohen-Bazire, G., Stanier, R. Y.: Biosynthesis of carotenoids in purple bacteria: A re-evaluation based on consideration of chemical structure. Nature (Lond.) 192, 1168–1172 (1961)

    Google Scholar 

  • Liaaen-Jensen, S., Jensen, A.: Quantitative determination of carotenoids in photosynthetic tissues. In: Methods of enzymology (S. P. Colowick, N. O. Kaplan, eds.), Vol. 23, pp. 586–602. New York: Academic Press 1971

    Google Scholar 

  • Mathews, M. M., Sistrom, W. R.: Function of carotenoid pigments in non-photosynthetic bacteria. Nature (Lond.) 184, 1892–1896 (1959)

    Google Scholar 

  • Mathews, M. M., Sistrom, W. R.: The function of carotenoid pigments of Sarcina lutea. Arch. Mikrobiol. 35, 139–146 (1960)

    Google Scholar 

  • Norgård, S., Aasen, A. J., Liaaen-Jensen, S.: Bacterial carotenoids. XXXII. C50-Carotenoids. 6. Carotenoids from Corynebacterium poinsettae including four new C50-diols. Acta chem. scand. 24, 2183–2197 (1970b)

    Google Scholar 

  • Norgård, S., Francis, G. W., Jensen, A., Liaaen-Jensen, S.: Bacterial carotenoids. XXXIV. C50-Carotenoids. 7. A C50-carotenol-D-glucoside from Sarcina lutea. Acta chem. scand. 24, 1460–1462 (1970a)

    Google Scholar 

  • Nybraaten, G., Liaaen-Jensen, S.: Bacterial carotenoids. XLIV. Zeaxanthin mono- and dirhamnoside. Acta chem. scand. B 28, 1219–1224 (1974)

    Google Scholar 

  • Schmidt, K.: Biosynthesis of carotenoids. In: Photosynthetic bacteria (R. K. Clayton, W. R. Sistrom, eds.). New York: Plenum Press 1976 (in press)

    Google Scholar 

  • Schneider, K., Rudolph, V., Schlegel, H. G.: Description and physiological characterization of a coryneform hydrogen bacterium strain 14 g. Arch. Microbiol. 93, 179–193 (1973)

    Google Scholar 

  • Stanier, R. Y.: Formation and function of the photosynthetic pigment system in purple bacteria. The photochemical apparatus: Its structure and function. Brookh. Symp. Biol. 11, 43–53 (1959)

    Google Scholar 

  • Stanier, R. Y., Cohen-Bazire, G.: The role of light in the microbial world: Some facts and speculations. Microbiol. Ecology, 7th Symp. Soc. Gen. Microbiol. (R. E. O. Williams, C. C. Spices, eds.), pp. 56–89, Cambridge: Cambridge Univ. Press 1957

    Google Scholar 

  • Stoddart, J. F.: Stereochemistry of carbohydrates, p. 55. London: Wiley 1971

    Google Scholar 

  • Sunada, K. V., Stanier, R. Y.: Observations on the pathway of carotenoid synthesis in Rhodopseudomonas. Biochim. biophys. Acta (Amst.) 107, 38–43 (1965)

    Google Scholar 

  • Tunail, N., Schlegel, H. G.: A new coryneform hydrogen bacterium: Corynebacterium autotrophicum strain 7C. 1. Characterization of the wild type strain. Arch. Microbiol. 100, 341–350 (1974)

    Google Scholar 

  • Vetter, W., Englert, G., Rigassi, N., Schwieter, U.: Spectroscopic methods. In: Carotenoids (O. Isler, ed.), pp. 189–266. Basel: Birkhäuser 1971

    Google Scholar 

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Dedicated to Professor R. Y. Stanier on his 60th birthday in appreciation of his studies on the function and biosynthesis of carotenoids and influence on the scientific development of his co-workers

No. XLIX: Acta chem. scand. (in press)

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Hertzberg, S., Borch, G. & Liaaen-Jensen, S. Bacterial carotenoids. Arch. Microbiol. 110, 95–99 (1976). https://doi.org/10.1007/BF00416974

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