Observation of the pathway from lysine to the isoprenoidal lipid of halophilic archaea, Halobacterium halobium and Natrinema pallidum, using regiospecifically deuterated lysine

Bulletin of the Chemical Society of Japan

Volumn 74, Issue 11, 2001, Pages 2199-2205

  Yamauchi, Noriaki ^a   Endoh, Satoshi ^a   Kato, Keiko ^a   Murae, Tatsushi ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; DEGRADATION; DEUTERIUM; LIPIDS; SYNTHESIS (CHEMICAL);

LIPID CORE;

AMINO ACIDS;

CARBOXYLIC ACID; COENZYME A; DEUTERIUM; ISOPRENOID; LIPID; LYSINE; MEVALONIC ACID;

AMINO ACID METABOLISM; ARCHAEBACTERIUM; ARTICLE; BACTERIAL METABOLISM; DECARBOXYLATION; DEGRADATION; HALOBACTERIUM SALINARUM; NATRINEMA PALLIDUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0035788647     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.74.2199     Document Type: Article

References (31)

1. a) C. R. Woese, O. Kadler, and M. L. Weelis, Proc. Natl. Acad. Sci. U.S.A., 87, 4576 (1990).
2. b) S. M. Bam, R. E. Fundyga, M. W. Jeffries, and N. R. Pace, Proc. Natl. Acad. Sci. U.S.A., 91, 1609 (1994).
3. a) T. A. Langworthy, "Lipids of archaebacteriae," in "The Bacteria," ed by C. R. Woese and R. S. Wolfe, Academic Press, New York (1985), Vol. 8, pp. 459-497.
4. b) M. Kates, "Membrane lipids of archaea," in "The Biochemistry of Archaea (Archaebacteria)," ed by M. Kates, D. J. Kushner, and A. T. Matheson, Elsevier, Amsterdam (1993), pp. 261-295.
5. M. Kates, Experientia, 49, 1027 (1993).
6. N. Moldoveanu and M. Kates, Biochem. Biophys. Acta, 960, 164 (1988).
7. a) T. Eguchi, M. Morita, and K. Kakinuma, J. Am. Chem. Soc., 120, 5427 (1998).
8. b) T. Eguchi, H. Takyo, M. Morita, and K. Kakinuma, Chem. Commun., 1545 (2000).
9. a) G. Flesek and M. Rohmer, Eur. J. Biochem., 175, 405 (1988).
10. b) M. Rohmer, M, Seemann, S. Horbach, S. Bringer-Meyer, and H. Sahm, J. Am. Chem. Soc., 118, 2564 (1996).
11. c) H. Seto, H. Watanabe, and K. Furihata, Tetrahedron Lett., 37, 7979 (1996).
12. d) J. Schwende, M. Seemann, H. K. Lichenthaler, and M. Rohmer, Biochem. J., 316, 73 (1996).
13. e) D. Arigon, S. Sagner, C. Latzel, W. Eisenbach, A. Bacher, and M. Zenk, Proc. Natl. Acad. Sci. U.S.A., 94, 10600 (1997).
14. I. Ekiel., G. D. Sprot, and I. C. P. Smith, J. Bacteriol., 166, 559 (1986).
15. N. Yamauchi, Y. Natsubori, and T. Murae, Bull. Chem. Soc. Jpn., 73, 2513 (2000).
16. L. L. Bieber, Ann. Rev. Biochem., 57, 261 (1988).
17. J. C. Fothrergill and J. R. Guest, J. Gen. Microbiol., 99, 139 (1977).
18. E. L. Pugh, M. K. Wassef, and M. Kates, Can. J. Biochem., 49, 953 (1971).
19. a) H. Misono, T. Yoshimura, S. Nagasaki, and K. Soda, J. Biochem., 107, 169 (1990).
20. b) T. Tsukkinoki, T. Mashima, M. Mukumoto, S. Makata, J. Udagawa, and M. Tashiro, J. Deuterium Sci., 3, 90 (1993).
21. c) J. Raap, W. N. Wolthus, J. J. J. Hehenkamp, and J. Lugtenburg, Amino Acids, 8, 171 (1995).
22. d) A. Sutherland and C. L. Willis, J. Labeled Compd, Radiopham., 38, 95 (1996).
23. a) D. J. Aberhart, H-J. Lin, and B. H. Weiller, J. Am. Chem. Soc., 103, 6750 (1981).
24. b) D. J. Aberhart, S. J. Gould, H-J. Lin, T. K. Thiruvengadam, and B. H. Weiller, J. Am. Chem. Soc., 105, 5461 (1983).
25. c) T. K. Thiruvengadem, S. J. Gould, D. J. Aberhart, and H-J. Lin, J. Am. Chem. Soc., 103, 5470 (1983).
26. H. Schneider, G. Sigmund, B. Schricker, K. Thirring, and H. Bemer, J. Org. Chem., 58, 683 (1993).
27. Natrinema pallidum was formerly known as Halobacterium halobium. a) T. J. Mcgenit, R. T. Gemmell, and W. D. Grant, Int. J. Syst. Bacteriol., 48, 1187 (1998).
28. b) K. Kamekura and M. Kates, Biosci. Biotech. Biochem., 63, 969 (1999).
29. Y-F. Chung and E. Adams, J. Biol. Chem., 252, 70979 (1977).
30. The stereochemistry of hydrogen abstruction at C-2 of IPP has been well established (stereospecific loss of pro-R hydrogen). The stereochemistry of hydrogen at C-2 of IPP could not imagined at this time because of stereochemical ambiguity at the step of the addition of a hydrogen atom corresponding to C-2 of IPP from crotonoyl-CoA to hydroxybutyryl-CoA.
31. W. V. Ng, S. P. Kennedy, G. G. Mahairas, B. Berquist, M. Pan, H. D. Shukla, S. R. Lasky, N. S. Baliga, V. Thorsson, J. Sbrogna, S. Swatzell, D. Weir, J. Hall, T. A. Dahl, R. Welti, Y. A. Goo, B. Leithauser, K. Keller. R. Cruz, M. J. Danson, D. W. Hough, D. G Maddocks, P. E. Jablonski, M. P. Krebs, C. M. Angevine, H. Dale, T. A. Lsenbarger, R. F. Peck, M. Pohlcshroder, J. L. Spudich, K-H. Jung, M. Alam, T. Feritas, S. Hou, C. J. Daniels, P. P. Dennis, A. D. Omer, H. Ebhaedt, T. M. Lowe, P. Liang, M. Riley, L. Hood, and S. DasSarma, Proc. Natl. Acad. Sci. U.S.A., 97, 12176 (2000).