Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

Journal of Lipid Research

Volumn 51, Issue 5, 2010, Pages 1017-1022

  Ter Horst, Bjorn ^a   Seshadri, Chetan ^b   Sweet, Lindsay ^b   Young, David C ^b   Feringa, Ben L ^a   Moody, D Branch ^b   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

Asymmetric 1,4 addition; MS MS analysis; Tuberculostearic acid

Indexed keywords

1 O TUBERCULOSTEAROYL 2 O PALMITOYL SN GLYCERO 3 PHOSPHOETHANOLAMINE; GLYCEROL; GLYCEROPHOSPHOLIPID; PHOSPHATIDYLETHANOLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BACTERIAL STRAIN; CHEMICAL STRUCTURE; LIPID ANALYSIS; LIPIDOMICS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PATHOGENICITY; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

BIOLOGICAL MARKERS; BIOLOGICAL PRODUCTS; GLYCEROPHOSPHOLIPIDS; MYCOBACTERIUM TUBERCULOSIS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TUBERCULOSIS;

EID: 77951056540     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M001982     Document Type: Article

References (40)

1. Vance, J. E. 2008. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. J. Lipid Res. 49: 1377-1387.
2. Nicolaou, K. C., and S. A. Snyder. 2005. Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation. Agnew. Chem. Int. Ed. 44: 1012-1044.
3. Smith, P. B., A. P. Snyder, and C. S. Harden. 1995. Characterization of bacterial phospholipids by electrospray ionization tandem mass spectrometry. Anal. Chem. 67: 1824-1830.
4. Cabrera, G. M., M. L. Fernández Murga, G. Font de Valdez, and A. M. Seldes. 2000. Direct analysis by electrospray ionisation tandem mass spectrometry of mixtures of phosphatidyldiacylglycerols from Lactobacillus. J. Am. Soc. Mass Spectrom. 35: 1452-1459. (Pubitemid 32063651)
5. Jensen, N. J., K. B. Tomer, and M. L. Gross. 1987. FAB MS/MS for phosphatidylinostitol,-glycerol,-ethanolamine and other complex phospholipids. Lipids. 22: 480-489.
6. Hsu, F-F., and J. Turk. 2000. Characterization of phosphatidylinositol, phosphatidylinositol-4-phosphate, and phosphatidylinositol-4,5-bisphosphate by electrospray ionization tandem mass spectrometry: a mechanistic study. J. Am. Soc. Mass Spectrom. 11: 986-999. (Pubitemid 34546669)
7. Hsu, F-F., and J. Turk. 2000. Charge-remote and charge-driven fragmentation processes in diacyl glycerophosphoethanolamine upon low-energy collisional activation: a mechanistic proposal. J. Am. Soc. Mass Spectrom. 11: 892-899. (Pubitemid 34546015)
8. Hsu, F-F., and J. Turk. 2000. Charge-driven fragmentation processes in diacyl glycerophosphatidic acids upon low-energy collisional activation. A mechanistic proposal. J. Am. Soc. Mass Spectrom. 11: 797-803. (Pubitemid 34532590)
9. Hsu, F-F., and J. Turk. 2004. Studies on sulfatides by quadrupole ion-trap mass spectrometry with electrospray ionization: structural characterization and the fragmentation processes that include an unusual internal galactose residue loss and the classical charge-remote fragmentation. J. Am. Soc. Mass Spectrom. 15: 536-546.
10. Hsu, F-F., J. Turk, R. M. Owens, E. R. Rhoades, and D. G. Russel. 2007. Structural characterization of phosphatidyl-myo-inositol mannosides from Mycobacterium bovis bacillus Calmette Guérin by multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. I. PIMs and lyso-PIMs. J. Am. Soc. Mass Spectrom. 18: 466-478. (Pubitemid 46274378)
11. Hsu, F-F., J. Turk, R. M. Owens, E. R. Rhoades, and D. G. Russel. 2007. Structural characterization of phosphatidyl-myo-inositol mannosides from Mycobacterium bovis bacillus Calmette Gú erin by multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. II. Monoacyl- and diacyl-PIMs. J. Am. Soc. Mass Spectrom. 18: 479-492.
12. Gilleron, M., C. Ronet, M. Mempel, B. Monsarrat, G. Gachelin, and G. Puzo. 2001. Acylation state of the phosphatidylinositol mannosides from Mycobacterium bovis bacillus Calmette Guérin and ability to induce granuloma and recruit natural killer T cells. J. Biol. Chem. 276: 34896-34904. (Pubitemid 33662492)
13. Gilleron, M., V. F. J. Quesniaux, and G. Puzo. 2003. Acylation state of the phosphatidylinositol hexamannosides from Mycobacterium bovis bacillus Calmette Guérin and Mycobacterium tuberculosis H37Rv and its implication in Toll-like receptor response. J. Biol. Chem. 278: 29880-29889.
14. Gilleron, M., B. Lindner, and G. Puzo. 2006. MS/MS approach for characterization of the fatty acid distribution on mycobacterial phosphatidyl-myo-inositol mannosides. Anal. Chem. 78: 8543-8548.
15. Dyer, B. S., J. D. Jones, G. D. Ainge, M. Denis, D. S. Larsen, and G. F. Painter. 2007. Synthesis and structure of phosphatidylinositol dimannoside. J. Org. Chem. 72: 3282-3288.
16. Matsunaga, I., A. Bhatt, D. C. Young, T-Y. Cheng, S. J. Eyles, G. S. Besra, V. Briken, S. A. Porcelli, C. E. Costello, W. R. Jacobs, Jr., et al. 2004. Mycobacterium tuberculosis pks12 produces a novel polyketide presented by CD1c to T cells. J. Exp. Med. 200: 1559-1569.
17. Anderson, R. J. 1927. A study of the phosphatide fraction of tubercle bacilli. J. Biol. Chem. 74: 537-551.
18. Spielman, M. A. 1934. The chemistry of the lipids of tubercle bacilli. XXXIX. The constitution of tuberculostearic acid. J. Biol. Chem. 106: 87-96.
19. Prout, F. S., J. Cason, and A. W. Ingersoll. 1947. The synthesis of tuberculostearic acid. J. Am. Chem. Soc. 69: 1233.
20. Prout, F. S., J. Cason, and A. W. Ingersoll. 1948. Branched-chain fatty acids. V. The synthesis of optically active 10-methyloctadecanoic acids. J. Am. Chem. Soc. 70: 298-305.
21. Linstead, R. P., J. C. Lunt, and B. C. L. Weedon. 1950. Anodic syntheses. Part II. Synthesis of (±)-tuberculostearic acid. J. Chem. Soc. 3331-3333.
22. Linstead, R. P., J. C. Lunt, and B. C. L. Weedon. 1951. Anodic syntheses. Part IV. Synthesis of (+)- and (-)-tuberculostearic acids. J. Chem. Soc. 1130-1132.
23. Hünig, S., and M. Salzwedel. 1966. Synthesen mit Enaminen, X. Systematische Synthese methylverzweigter Carbonsäuren. Chem. Ber. 99: 823-842.
24. Wallace, P. A., D. E. Minnikin, K. McCrudden, and A. Pizzarello. 1994. Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates. Chem. Phys. Lipids. 71: 145-162.
25. Liu, X., B. L. Stocker, and P. H. Seeberger. 2006. Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis. J. Am. Chem. Soc. 128: 3638-3648.
26. Roberts, I. O., and M. S. Baird. 2006. A new short synthesis of 10R-tuberculostearic acid and its enantiomer. Chem. Phys. Lipids. 142: 111-117. (Pubitemid 43766320)
27. Van Zijl, A. W., A. J. Minnaard, and B. L. Feringa. 2008. Straightforward synthesis of alpha,beta-unsaturated thioesters via ruthenium-catalyzed olefin cross-metathesis with thioacrylate. J. Org. Chem. 73: 5651-5653.
28. Mazery, R., M. Pullez, F. López, S. R. Harutyunyan, A. J. Minnaard, and B. L. Feringa. 2005. An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of Grignard reagents to α,β-unsaturated thioesters. J. Am. Chem. Soc. 127: 9966-9967.
29. Ter Horst, B., B. L. Feringa, and A. J. Minnaard. 2007. Catalytic asymmetric synthesis of mycocerosic acid. Chem. Commun. (Camb.). 5: 489-491. (Pubitemid 46155897)
30. Ter Horst, B., B. L. Feringa, and A. J. Minnaard. 2007. Catalytic asymmetric synthesis of phthioceranic acid, a heptamethyl-branched acid from Mycobacterium tuberculosis. Org. Lett. 9: 3013-3015.
31. Howell, G. P., S. P. Fletcher, K. Geurts, B. ter Horst, and B. L. Feringa. 2006. Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions. J. Am. Chem. Soc. 128: 14977-14985.
32. Harutyunyan, S. R., Z. Zhao, T. den Hartog, K. Bouwmeester, A. J. Minnaard, B. L. Feringa, and F. Govers. 2008. Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis. Proc. Natl. Acad. Sci. USA. 105: 8507-8512.
33. Van Zijl, A. W., W. Szymanski, F. López, A. J. Minnaard, and B. L. Feringa. 2008. Catalytic enantioselective synthesis of vicinal dialkyl arrays. J. Org. Chem. 73: 6994-7002.
34. Fukuyama, T., and H. Tokuyama. 2004. Palladium-mediated synthesis of aldehydes and ketones from thiol esters. Aldrichim Acta. 37: 87-96.
35. Smit, C., M. W. Fraaije, and A. J. Minnaard. 2008. Reduction of carbon-carbon double bonds using organocatalytically generated diimide. J. Org. Chem. 73: 9482-9485.
36. Eibl, H. 1978. Phospholipid synthesis: oxazaphospholanes and dioxaphospholanes as intermediates. Proc. Natl. Acad. Sci. USA. 75: 4074-4077.
37. Baer, E., and D. Buchnea. 1958. Synthesis of unsaturated alpha-phosphatidic acids and alpha-bisphosphatidic acids; cardiolipin substitutes. IV. Arch. Biochem. Biophys. 78: 294-305.
38. Rzepecki, P. W., and G. D. Prestwich. 2002. Synthesis of hybrid lipid probes: derivatives of phosphatidylethanolamine-extended phosphatidylinositol 4,5-bisphosphate (Pea-PIP2). J. Org. Chem. 67: 5454-5460.
39. Campbell, A. S., and B. Fraser-Reid. 1994. Support studies for installing the phosphodiester residues of the Thy-1 glycoprotein membrane anchor. Bioorg. Med. Chem. 2: 1209-1219.
40. Subrahmanyam, D. 1965. Fatty acid composition of phosphatidyl ethanolamine of Mycobacterium tuberculosis. Indian J. Biochem. 2: 274-275.