The synthesis of archaebacterial lipid analogues

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2971-2974

  Raguse, Burkhard ^a,b   Culshaw, Peter N ^a,b   Prashar, Jognandan K ^a,c   Raval, Kiran ^a,d  

^a 126 Greville St ^*  (Australia)

^b CSIRO   (Australia)

^c UNIVERSITY OF SYDNEY   (Australia)

^d Ambri Pty Ltd   (Australia)

Author keywords

Archaebacteria; Biosensors; Lipids; Membrane spanning lipids; Membranes

Indexed keywords

ARCHAEBACTERIUM LIPID; LIPID; UNCLASSIFIED DRUG;

ARCHAEBACTERIUM; ARTICLE; BIOSENSOR; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR STABILITY; NONHUMAN;

EID: 0034656159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00283-5     Document Type: Article

References (23)

1. Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. Nature 1997, 387, 580; Raguse, B.; Braach-Maksvytis, V.; Cornell, B. A.; King, L. G.; Osman, P. D. J.; Pace, R. J.; Wieczorek, L. Langmuir 1998, 14, 648; Pace, R. J.; Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L. SPIE Proc. 1998, 3270, 50; Woodhouse, G. E.; King, L. G.; Wieczorek, L.; Cornell, B. A. Faraday Discuss. 1998, 111, 247.
2. Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. Nature 1997, 387, 580; Raguse, B.; Braach-Maksvytis, V.; Cornell, B. A.; King, L. G.; Osman, P. D. J.; Pace, R. J.; Wieczorek, L. Langmuir 1998, 14, 648; Pace, R. J.; Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L. SPIE Proc. 1998, 3270, 50; Woodhouse, G. E.; King, L. G.; Wieczorek, L.; Cornell, B. A. Faraday Discuss. 1998, 111, 247.
3. Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. Nature 1997, 387, 580; Raguse, B.; Braach-Maksvytis, V.; Cornell, B. A.; King, L. G.; Osman, P. D. J.; Pace, R. J.; Wieczorek, L. Langmuir 1998, 14, 648; Pace, R. J.; Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L. SPIE Proc. 1998, 3270, 50; Woodhouse, G. E.; King, L. G.; Wieczorek, L.; Cornell, B. A. Faraday Discuss. 1998, 111, 247.
4. Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. Nature 1997, 387, 580; Raguse, B.; Braach-Maksvytis, V.; Cornell, B. A.; King, L. G.; Osman, P. D. J.; Pace, R. J.; Wieczorek, L. Langmuir 1998, 14, 648; Pace, R. J.; Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L. SPIE Proc. 1998, 3270, 50; Woodhouse, G. E.; King, L. G.; Wieczorek, L.; Cornell, B. A. Faraday Discuss. 1998, 111, 247.
5. Woese, C.; Wheelis, M. L. Proc. Natl. Acad. Sci. USA 1990, 87, 4576; Woese, C. R. Microbiol. Rev. 1987, 51, 221; Woese, C. R. Sci. Am. 1981, 244, 98.
6. Woese, C.; Wheelis, M. L. Proc. Natl. Acad. Sci. USA 1990, 87, 4576; Woese, C. R. Microbiol. Rev. 1987, 51, 221; Woese, C. R. Sci. Am. 1981, 244, 98.
7. Woese, C.; Wheelis, M. L. Proc. Natl. Acad. Sci. USA 1990, 87, 4576; Woese, C. R. Microbiol. Rev. 1987, 51, 221; Woese, C. R. Sci. Am. 1981, 244, 98.
8. Gräther, O.; Arigoni, D. J. Chem. Soc., Chem. Commun. 1995, 405, and references cited therein; Luzzati, V.; Gambacorta, A.; DeRosa, M.; Gulik, A. Annu. Rev. Biophys. Biophys. Chem. 1987, 16, 25; Kates, M. In The Biochemistry of Archae (Archaebacteria); Kates, M.; Kushner, D. J.; Matheson, A. T., Eds.; Elsevier: Amsterdam, 1993; pp. 261.
9. Gräther, O.; Arigoni, D. J. Chem. Soc., Chem. Commun. 1995, 405, and references cited therein; Luzzati, V.; Gambacorta, A.; DeRosa, M.; Gulik, A. Annu. Rev. Biophys. Biophys. Chem. 1987, 16, 25; Kates, M. In The Biochemistry of Archae (Archaebacteria); Kates, M.; Kushner, D. J.; Matheson, A. T., Eds.; Elsevier: Amsterdam, 1993; pp. 261.
10. Gräther, O.; Arigoni, D. J. Chem. Soc., Chem. Commun. 1995, 405, and references cited therein; Luzzati, V.; Gambacorta, A.; DeRosa, M.; Gulik, A. Annu. Rev. Biophys. Biophys. Chem. 1987, 16, 25; Kates, M. In The Biochemistry of Archae (Archaebacteria); Kates, M.; Kushner, D. J.; Matheson, A. T., Eds.; Elsevier: Amsterdam, 1993; pp. 261.
11. The Achaebacteria: Biochemistry and Biotechnology; Danson, M. J.; Hough, D. W.; Lunt, G. G., Eds.; Portland Press: Chapel Hill, 1992; Gambacorta, A.; Gliozzi, A.; De Rosa, M. World J. Microbiol. Biotechnol. 1995, 11, 115; De Rosa, M.; Lanzotti, V.; Nicolaus, B.; Trincone, A.; Gambacorta, A. In Microbiology of Extreme Environments and its Potential for Biotechnology; Da Costa, M. S.; Duarte, J. C.; Williams, R. A. D., Eds.; Elsevier: London, 1989; pp. 131.
12. The Achaebacteria: Biochemistry and Biotechnology; Danson, M. J.; Hough, D. W.; Lunt, G. G., Eds.; Portland Press: Chapel Hill, 1992; Gambacorta, A.; Gliozzi, A.; De Rosa, M. World J. Microbiol. Biotechnol. 1995, 11, 115; De Rosa, M.; Lanzotti, V.; Nicolaus, B.; Trincone, A.; Gambacorta, A. In Microbiology of Extreme Environments and its Potential for Biotechnology; Da Costa, M. S.; Duarte, J. C.; Williams, R. A. D., Eds.; Elsevier: London, 1989; pp. 131.
13. The Achaebacteria: Biochemistry and Biotechnology; Danson, M. J.; Hough, D. W.; Lunt, G. G., Eds.; Portland Press: Chapel Hill, 1992; Gambacorta, A.; Gliozzi, A.; De Rosa, M. World J. Microbiol. Biotechnol. 1995, 11, 115; De Rosa, M.; Lanzotti, V.; Nicolaus, B.; Trincone, A.; Gambacorta, A. In Microbiology of Extreme Environments and its Potential for Biotechnology; Da Costa, M. S.; Duarte, J. C.; Williams, R. A. D., Eds.; Elsevier: London, 1989; pp. 131.
14. Yamauchi, K.; Moriya, A.; Kinoshita, M. Biochim. Biophys. Acta 1989, 1003, 151.
15. Moss, R. A.; Li, J.-M. J. Am. Chem. Soc. 1992, 114, 9227; Moss, R. A.; Fujita, T.; Okumura, Y. Langmuir 1991, 7, 2415.
16. Moss, R. A.; Li, J.-M. J. Am. Chem. Soc. 1992, 114, 9227; Moss, R. A.; Fujita, T.; Okumura, Y. Langmuir 1991, 7, 2415.
17. Joo, C. N.; Shier, T.; Kates, M. J. Lipid Res. 1968, 9, 782.
18. In this work racemic glycerol and a mixture of stereoisomers of phytanol were employed. For routes to stereochemically pure phytanol, see: Sita, L. R. J. Org. Chem. 1993, 58, 5285; Burns, C. J.; Field, L. D.; Hashimoto, K.; Petteys, B. J.; Ridley, D. D.; Rose, M. Aust. J. Chem. 1999, 52, 387.
19. In this work racemic glycerol and a mixture of stereoisomers of phytanol were employed. For routes to stereochemically pure phytanol, see: Sita, L. R. J. Org. Chem. 1993, 58, 5285; Burns, C. J.; Field, L. D.; Hashimoto, K.; Petteys, B. J.; Ridley, D. D.; Rose, M. Aust. J. Chem. 1999, 52, 387.
20. Crich, D.; Beckwith, A. L. J.; Chen, C.; Yao, Q.; Davison, I. G. E.; Longmore, R. W.; Anaya de Parrodi, C.; Quintero-Cortes, L.; Sandoval-Ramirez, J. J. Am. Chem. Soc. 1995, 117, 8757.
21. Aragozzini, F.; Maconi, E.; Ponteza, D.; Scolastico, C. Synthesis 1989, 225.
22. 4, 95%).
23. 8 requires: C,78.4; H, 12.1%.