Determination of the configuration of an Archaea membrane lipid containing cyclopentane rings by total synthesis

Angewandte Chemie - International Edition

Volumn 42, Issue 21, 2003, Pages 2419-2421

  Montenegro, Elvira ^a   Gabler, Bert ^a   Paradies, Gesa ^a   Seemann, Matthias ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Archaea membrane lipids; Asymmetric synthesis; Configuration determination; Cross coupling; Natural products

Indexed keywords

BIOLOGICAL MEMBRANES; GLYCEROL; SYNTHESIS (CHEMICAL);

LIPOSOMES;

LIPIDS;

CARBOHYDRATE DERIVATIVE; CYCLOPENTANE; ETHER DERIVATIVE; GLYCEROL; ISOPRENOID; LIPOSOME; MEMBRANE LIPID;

ARCHAEBACTERIUM; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROGENATION; LIPID ANALYSIS; LIPID COMPOSITION; LIPOGENESIS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

ARCHAEA; MEMBRANE LIPIDS; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 0038681993     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250629     Document Type: Article

References (31)

1. a) C. R. Woese, O. Kandler, M. L. Wheelis, Proc. Natl. Acad. Sci. USA 1990, 87, 4576-4759;
2. b) G. Darland, T. D. Brock, W. Samsonoff, S. F. Conti, Science 1970, 170, 1416-1418;
3. c) K. O. Stetter, Naturwissenschaften 1985, 72, 291-301;
4. d) T. D. Brock, Science 1985, 230, 132-138.
5. a) S. Thurl, PhD thesis, Technische Universität, Munich, 1986;
6. b) Y. Blériot, E. Untersteller, B. Fritz, P. Sinaÿ, Chem. Eur. J. 2002, 8, 240-246;
7. c) A. J. Fairbanks, P. Sinaÿ, Tetrahedron Lett. 1995, 36, 893-896;
8. d) M. De Rosa, A. Gambacorta, A. Gliozzi, Microbiol. Rev. 1986, 70-80.
9. "Archaeal Lipids": M. De Rosa, A. Gambacorta in Chemical Methods in Bacterial Systematics (Eds.: M. Goodfellow, A. G. O'Donell), Wiley, Chicester, 1994, pp. 197-264.
10. a) T. Eguchi, K. Arakawa, T. Terachi, K. Kakinuma, J. Org. Chem. 1997, 62, 1924-1933;
11. b) T. Eguchi, T. Terachi, K. Kakinuma, J. Chem. Soc. Chem. Commun. 1994, 7-8.
12. a) C. H. Heathcock, B. L. Finkelstein, E. T. Jarvi, P. A. Radel, C. R. Hadley, J. Org. Chem. 1988, 53, 1922-1942.
13. T. Eguchi, K. Ibaragi, K. Kakinuma, J. Org. Chem. 1998, 63, 2689-2698.
14. a) M. De Rosa, S. De Rosa, A. Gambacorta, L. Minale, J. D. Bu'Lock, Phytochemistry 1977, 16, 1661-1965;
15. b) M. De Rosa, S. De Rosa, Phytochemistry 1977, 16, 1909-1912.
16. a) L. L. Yang, A. Haug, Biochim. Biophys. Acta 1979, 573, 308-320;
17. b) H. Hanselaer, P. De Clercq, Org. Magn. Reson. 1980, 13, 376-379;
18. c) M. Christl, H. J. Reich, J. D. Roberts, J. Am. Chem. Soc. 1971, 93, 3463-3468.
19. a) G. Knühl, P. Sennhenn, G. Helmchen, J. Chem. Soc. Chem. Commun. 1995, 1845-1846;
20. b) S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210-3212; Angew. Chem. Int. Ed. 1998, 37, 3047-3050;
21. b) S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210-3212; Angew. Chem. Int. Ed. 1998, 37, 3047-3050;
22. c) S. Kudis, G. Helmchen, Tetrahedron 1998, 54, 10449-10456.
23. a) V. K. Aggarwal, N. Monteiro, G. J. Tarver, R. McCague, J. Org. Chem. 1997, 62, 4665-4671.
24. a) D. Curran, M.-H. Chen, D. Leszczweski, R. L. Elliott, D. M. Rakiewicz, J. Org. Chem. 1986, 51, 1612-1614;
25. b) H. L. Goering, S. S. Kantner, J. Org. Chem. 1984, 49, 422-426.
26. a) M. Tamura, J. Kochi, Synthesis 1971, 303-305;
27. b) G. Fouquet, M. Schlosser, Angew. Chem. 1974, 86, 50-51; Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
28. b) G. Fouquet, M. Schlosser, Angew. Chem. 1974, 86, 50-51; Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
29. A. G. Schultz, T. J. Guzi, E. Larsson, R. Rahm, K. Thakkar, J. Bidlack, J. Org. Chem. 1998, 63, 7795-7805.
30. The mixture of lipids was obtained from Bernina Biosystems, Munich. Degradation was carried out according to a method developed in the Arigoni goup (O. W. Gräther, PhD thesis, ETH Zürich, 1994): reaction with HI followed by treatment of the resultant iodides with silver acetate to give acetates which were saponified.
31. B. Gabler, PhD thesis, Universität Heidelberg, 1997.