Abstract
Isotopes have been crucial for the elucidation of numerous metabolic pathways such as the photosynthetic CO2 fixation cycle of plants, for which the Nobel Prize was awarded to Melvin Calvin. On the other hand, it is important to note that the biosynthetic literature is replete with incorrect conclusions derived from isotopic studies. To give just one example, numerous plant terpenes have been claimed incorrectly to be biosynthesized via the mevalonate pathway on the basis of studies with radiolabeled precursors. Only recently, the biosynthesis of many plant terpenoids versus the hitherto unknown deoxyxylulose pathway has been established [for reviews see (1–3)].
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Eisenreich, W., Schwarz, M., Cartayrade, A., Arigoni, D., Zenk, M.H. and Bacher, A. (1998) Chem. Biol. 5, R221–R233.
Rohmer, M. (1998) Prog. Drug Res. 50, 135–154.
Rohmer, M. (1999) in Comprehensive Natural Product Chemistry (D. Barton and K. Nakanishi, eds.) vol. 2, pp. 45–68, Pergamon, Oxford.
Drawert, F. and Beier, J. (1976) Phytochemistry 15, 1689–1690.
Goese, M., Kammhuber, K., Bacher, A., Zenk, M.H. and Eisenreich, W. (1999) Eur. J. Biochem. 263, 447–454.
Drawert, F. and Beier, J. (1974) Phytochemistry 13, 2749–2753.
Fraser, C.M. et al. (1995) Science 270, 397–403.
Rieder, C., Strau B., G., Fuchs, G., Arigoni, D., Bacher, A. and Eisenreich, W. (1998) J. Biol. Chem. 273, 18099–18108.
Werner, I., Bacher, A. and Eisenreich, W. (1997) J. Biol. Chem. 272, 25474–25482.
Eisenreich, W., Kupfer, E., Weber, W. and Bacher, A. (1997) J. Biol. Chem. 272, 867–874.
Beart, J.E., Lilley, T.H. and Haslam, E. (1985) Phytochemistry 24, 33–38.
Sawa, T. Nakao, M., Akaike, T., Ono, K. and Maeda, H. (1999) J. Agric. Food Chem. 47, 397–402.
Brucker, W. (1957) Planta 48, 627–630.
Brucker, W. and Drehmann, U. (1958) Archiv Mikrobiol. 30, 396–408.
Brucker, W. and Hashem, M. (1962) Ber. Dt. Bot. Gesell. 75, 3–13.
Zenk, M.H. (1964) Z. Naturforsch. 19b, 83–84.
Neish, A.C., Towers, G.H.N., Chen, D., El-Basyouni, S.Z. and Ibrahim, R.K. (1964) Phytochemistry 3, 485–492.
Haslam, E., Haworth, R.D. and Knowles, P.F. (1961) J. Chem. Soc. 1854–1859.
Dewick, P.M. and Haslam, E. (1968) Chem. Commun. 673–675.
Cornthwaite, D.C. and Haslam, E. (1965) J. Chem. Soc. 3008–3011.
Conn, E.E. and Swain, T. (1961) Chem. Ind. 592–593.
Marigo, G., Alibert, G. and Boudet, A. (1969) C. R. Acad. Sci. Ser. D 269, 1852–1854.
Dewick, P.M. and Haslam, E. (1969) Biochem. J. 113, 537–542.
Ishikura, N., Hayashida, S. and Tazaki, K. (1984) Bot. Mag. 97, 355–367.
Haslam, E. and Cai, Y. (1994) in Natural Product Reports, Vol. 11, pp. 41–66.
Werner, I., Bacher, A. and Eisenreich, W. (1999) in Plant Polyphenols 2: Chemistry and Biology (G. G. Gross, R. W. Hemingway, T. Yoshida eds.), Plenum, New York, NY (in press).
Bochar, D.A., Friesen, J.A., Stauffacher, C.V. and Rodwell, V.W. (1999) in Comprehensive Natural Product Chemistry (D. Barton, K. Nakanishi, eds.), vol. 2, pp. 15–44, Pergamon, Oxford.
Flesch, G. and Rohmer, M. (1988) Eur. J. Biochem. 175, 405–411.
Rohmer, M., Knani, M., Simonin, P., Sutter, B. and Sahm, H. (1993) Biochem. J. 295, 517–524.
Broers, S.T.J. (1994) Thesis Nr. 10978, ETH Zürich, Switzerland.
Schwarz, M.K. (1994) Thesis Nr. 19051, ETH Zürich, Switzerland.
Sprenger, G.A., Schorken, U., Wiegert, T., Grolle, S., deGraaf, A.A., Taylor, S.V., Begley, T.P., Bringer-Meyer, S. and Sahm, H. (1997) Proc. Nat. Acad. Sci. U.S.A. 94, 12857–12862.
Lois, L.M., Campos, N., Putra, S.R., Danielsen, K., Rohmer, M. and Boronat, A. (1998) Proc. Nat. Acad. Sci. U.S.A. 95, 2105–2110.
Takahashi, S., Kuzuyama, T., Watanabe, H. and Seto, H. (1998) Proc. Nat. Acad. Sci. U.S.A. 95, 9879–9884.
Lange, B.M. and Croteau, R. (1999) Arch. Biochem. Biophys. 365, 170–174.
Schwender, J., Müller, C., Zeidler, J. and Lichtenthaler, H.K. (1999) FEBS Lett. 455, 140–144.
Kingston, D.G.I.A., Molinaro, A.A. and Rimoldi, J.M. (1993) in Progress in the Chemistry of Organic Natural Products, Vol. 61, pp. 1–192, Springer Verlag, Vienna, New York, NY.
Wani, M.C., Taylor, H.L., Wall, M.E., Coggon, P. and McPhail, A.T. (1971) J. Amer. Chem. Soc. 93, 2325–2327.
Guéritte-Voegelein, F., Sénilh, V., David, B., Guénard, D. and Potier, P. (1986) Tetrahedron 42, 4451–4460.
Zamir, L.O., Nedea, M.E. and Garneau, F.X. (1992) Tetrahedron Lett. 33, 5235–5236.
Eisenreich, W., Menhard, B., Hylands, P.J., Zenk, M.H. and Bacher, A. (1996) Proc. Nat. Acad. Sci. U.S.A. 93, 6431–6436.
Koepp, A.E., Hezari, M., Zajicek, J., Stofer-Vogel, B., La Fever, R.E., Lewis, N.G. and Croteau, R. (1995) J. Biol. Chem. 270, 8686–8690.
Gatenbeck, S. (1962) Acta Chem. Scand. 16, 1053–1054.
Leistner, E. and Zenk, M.H. (1969) J. Chem. Soc. Chem. Commun. 210–211.
Paulick, R.C., Casey, M.L., Hillenbrand, D.F. and Whitlock, H.W. (1975) J. Amer. Chem. Soc. 97, 5303–5305.
Luckner, M. (1984) in Secondary Metabolism in Microorganisms, Plants and Animals, 3rd revised edition, 176–178, Springer Verlag.
Leistner, E. and Zenk, M.H. (1987) Z. Naturforsch. 22b, 865–868.
Campbell, I.M. (1969) Tetrahedron Lett. 54, 4777–4780.
Leistner, E. (1973a) Phytochemistry 12, 337–345.
Leistner, E. (1973b) Phytochemistry 12, 1669–1674.
Leistner, E. and Zenk, M.H. (1968) Tetrahedron Lett. 11, 1395–1396.
Burnett, A.R. and Thomson, R.H. (1968) J. Chem. Soc. C 17, 2437–2441.
Eichinger, D., Bacher, A., Zenk, M.H. and Eisenreich, W. (1999) J. Amer. Chem. Soc. 121, 7469–7475.
Eisenreich, W., Sagner, S., Zenk, M.H. and Bacher, A. (1997) Tetrahedron Lett. 38, 3889–3892.
Weber, S., Eisenreich, W., Bacher, A. and Hartmann, T. (1999) Phytochemistry 50, 1005–1014.
Goese, M., Kammhuber, K., Bacher, A., Zenk, M.H. and Eisenreich, W. (1999) Eur. J. Biochem. 263, 447–454.
Eichinger, D., Bacher, A., Zenk, M.H. and Eisenreich, W. (1999) Phytochemistry 51, 223–236.
Uesato, S., Kanomi, S., Iida, A., Inouye, H. and Zenk, M.H. (1986) Phytochemistry 25, 839–842.
Roãmao, M.J., Archer, M., Moura, I., Moura, J.J.G., LeGall, J., Engh, R., Schneider, M., Hof, P. and Huber, R. (1995) Science 270, 1170–1176.
Schindelin, H., Kisker, C., Hilton, J., Rajagopalan, K.V. and Rees, D.C. (1996) Science 272, 1615–1621.
Boyington, J.C., Gladyshev, V.N., Khangulov, S.K., Stadtman, T.C. and Sun, P.D. (1997) Science 275, 1305–1308.
Chan, M.K., Mukund, S., Kletzin, A., Adams, M.W.W. and Rees, D.C. (1995) Science 267, 1463–1469.
Kwon, N.S., Nathan, C.F. and Stuehr, D.J. (1989) J. Biol. Chem. 264, 20496–20501.
Irby, R.B. and Adair, W.L., Jr. (1994) J. Biol. Chem. 269, 23981–23987.
Wuebbens, M.M. and Rajagopalan, K.V. (1995) J. Biol. Chem. 270, 1082–1087.
Rieder, C., Eisenreich, W., O’Brien, J., Richter, G., Götze, E., Boyle, P., Blanchard, S., Bacher, A. and Simon, H. (1998) Eur. J. Biochem. 255, 24–36.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Springer Science+Business Media New York
About this chapter
Cite this chapter
Eisenreich, W., Bacher, A. (2000). Elucidation of Biosynthetic Pathways by Retrodictive/Predictive Comparison of Isotopomer Patterns Determined by NMR Spectroscopy. In: Setlow, J.K. (eds) Genetic Engineering. Genetic Engineering, vol 22. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4199-8_8
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4199-8_8
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-6884-7
Online ISBN: 978-1-4615-4199-8
eBook Packages: Springer Book Archive