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International Journal of Carbohydrate Chemistry
Volume 2011 (2011), Article ID 749591, 13 pages
Endogenous and Exogenous CD1-Binding Glycolipids
1School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington 6012, New Zealand
2Malaghan Institute of Medical Research, P.O. Box 7060, Wellington 6242, New Zealand
Received 15 August 2010; Revised 24 December 2010; Accepted 9 February 2011
Academic Editor: Yuriy A. Knirel
Copyright © 2011 Janice M. H. Cheng et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- R. Pfeiffer, “Untersuchungen über das Choleragift,” Zeitschrift für Hygiene und Infektionskrankheiten, vol. 11, no. 1, pp. 393–412, 1892.
- K. Landsteiner and P. Levine, “On individual differences in human blood,” Journal of Experimental Medicine, vol. 47, no. 5, pp. 757–775, 1928.
- C. R. H. Raetz and C. Whitfield, “Lipopolysaccharide endotoxins,” Annual Review of Biochemistry, vol. 71, pp. 635–700, 2002.
- T. J. Painter, W. M. Watkins, and W. T. J. Morgan, “Serologically active fucose-containing oligosaccharides isolated from human blood-group A and B substances,” Nature, vol. 206, no. 4984, pp. 594–597, 1965.
- F. Calabi, J. M. Jarvis, L. Martin, and C. Milstein, “Two classes of CD1 genes,” European Journal of Immunology, vol. 19, no. 2, pp. 285–292, 1989.
- D. B. Moody, D. M. Zajonc, and I. A. Wilson, “Anatomy of CD1-lipid antigen complexes,” Nature Reviews Immunology, vol. 5, no. 5, pp. 387–399, 2005.
- D. B. Moody, B. B. Reinhold, M. R. Guy et al., “Structural requirements for glycolipid antigen recognition by CD1b- restricted T cells,” Science, vol. 278, no. 5336, pp. 283–286, 1997.
- T. Kawano, J. Cui, Y. Koezuka et al., “CD1d-restricted and TCR-mediated activation of V(α)14 NKT cells by glycosylceramides,” Science, vol. 278, no. 5343, pp. 1626–1629, 1997.
- T. I. Prigozy, O. Naidenko, P. Qasba et al., “Glycolipid antigen processing for presentation by CD1d molecules,” Science, vol. 291, no. 5504, pp. 664–667, 2001.
- S. A. Porcelli, “Cutting glycolipids down to size,” Nature Immunology, vol. 2, no. 3, pp. 191–192, 2001.
- M. Salio, J. D. Silk, and V. Cerundolo, “Recent advances in processing and presentation of CD1 bound lipid antigens,” Current Opinion in Immunology, vol. 22, no. 1, pp. 81–88, 2010.
- D. Zhou, J. Mattner, C. Cantu et al., “Lysosomal glycosphingolipid recognition by NKT cells,” Science, vol. 306, no. 5702, pp. 1786–1789, 2004.
- S. Ahmad, “iGb3: to be or not to be?” Nature Reviews Immunology, vol. 7, no. 5, p. 325, 2007.
- E. M. Beckman, S. A. Porcelli, C. T. Morita, S. M. Behar, S. T. Furlong, and M. B. Brenner, “Recognition of lipid antigen by CD1-restricted αβ+ T cells,” Nature, vol. 372, no. 6507, pp. 691–694, 1994.
- K. Fischer, E. Scotet, M. Niemeyer et al., “Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells,” Proceedings of the National Academy of Sciences of the United States of America, vol. 101, no. 29, pp. 10685–10690, 2004.
- N. A. Parlane, M. Denis, W. B. Severn et al., “Phosphatidylinositol mannosides are efficient mucosal adjuvants,” Immunological Investigations, vol. 37, no. 2, pp. 129–142, 2008.
- P. A. Sieling, D. Chatterjee, S. A. Porcelli et al., “CD1-restricted T cell recognition of microbial lipoglycan antigens,” Science, vol. 269, no. 5221, pp. 227–230, 1995.
- J. Mattner, K. L. DeBord, N. Ismail et al., “Exogenous and endogenous glycolipid antigens activate NKT cells during microbial infections,” Nature, vol. 434, no. 7032, pp. 525–529, 2005.
- D. M. Zajonc, M. A. Elsliger, L. Teyton, and I. A. Wilson, “Crystal structure of CD1a in complex with a sulfatide self antigen at a resolution of 2.15 Å,” Nature Immunology, vol. 4, no. 8, pp. 808–815, 2003.
- A. Shamshiev, H. J. Gober, A. Donda, Z. Mazorra, L. Mori, and G. de Libero, “Presentation of the same glycolipid by different CD1 molecules,” Journal of Experimental Medicine, vol. 195, no. 8, pp. 1013–1021, 2002.
- D. M. Zajonc, I. Maricic, D. Wu et al., “Structural basis for CD1d presentation of a sulfatide derived from myelin and its implications for autoimmunity,” Journal of Experimental Medicine, vol. 202, no. 11, pp. 1517–1526, 2005.
- F. Compostella, L. Franchini, G. De Libero, G. Palmisano, F. Ronchetti, and L. Panza, “CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety,” Tetrahedron, vol. 58, no. 43, pp. 8703–8708, 2002.
- L. Franchini, P. Matto, F. Ronchetti et al., “Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue,” Bioorganic and Medicinal Chemistry, vol. 15, no. 16, pp. 5529–5536, 2007.
- S. D. Gadola, N. R. Zaccai, K. Harlos et al., “Structure of human CDIb with bound ligands at 2.3 Å, a maze for alkyl chains,” Nature Immunology, vol. 3, no. 8, pp. 721–726, 2002.
- D. B. Moody, V. Briken, T. Y. Cheng et al., “Lipid length controls antigen entry into endosomal and nonendosomal pathways for CD1b presentation,” Nature Immunology, vol. 3, no. 5, pp. 435–442, 2002.
- A. J. Steck, A. K. Stalder, and S. Renaud, “Anti-myelin-associated glycoprotein neuropathy,” Current Opinion in Neurology, vol. 19, no. 5, pp. 458–463, 2006.
- A. Shamshiev, A. Donda, T. I. Prigozy et al., “The αβ T cell response to self-glycolipids shows a novel mechanism of CD1b loading and a requirement for complex oligosaccharides,” Immunity, vol. 13, no. 2, pp. 255–264, 2000.
- M. Sugimoto, M. Numata, K. Koike, Y. Nakahara, and T. Ogawa, “Total synthesis of gangliosides GM1 and GM2,” Carbohydrate Research, vol. 156, pp. C1–C5, 1986.
- S. K. Bhattacharya and S. J. Danishefsky, “A total synthesis of the methyl glycoside of ganglioside GM1,” Journal of Organic Chemistry, vol. 65, no. 1, pp. 144–151, 2000.
- A. Shamshiev, A. Donda, I. Carena, L. Mori, L. Kappos, and G. De Libero, “Self glycolipids as T-cell autoantigens,” European Journal of Immunology, vol. 29, no. 5, pp. 1667–1675, 1999.
- H. K. Ishida, H. Ishida, M. Kiso, and A. Hasegawa, “Total synthesis of ganglioside GQ1b,” Carbohydrate Research, vol. 260, no. 2, pp. C1–C6, 1994.
- R. Kuhn and H. Wiegandt, “Die Konstitution der Ganglio-N-tetraose und des Gangliosids GI,” Chemische Berichte, vol. 96, pp. 866–880, 1963.
- S. Ando and R. K. Yu, “Isolation and characterization of two isomers of brain tetrasialogangliosides,” Journal of Biological Chemistry, vol. 254, no. 23, pp. 12224–12229, 1979.
- P. Fredman, J. E. Mansson, L. Svennerholm, K. A. Karlsson, I. Pascher, and B. E. Samuelsson, “The structure of the tetrasialoganglioside from human brain,” FEBS Letters, vol. 110, no. 1, pp. 80–84, 1980.
- A. Imamura, H. Ando, H. Ishida, and M. Kiso, “Ganglioside GQ1b: efficient total synthesis and the expansion to synthetic derivatives to elucidate its biological roles,” Journal of Organic Chemistry, vol. 74, no. 8, pp. 3009–3023, 2009.
- S. Ando, M. Isobe, and Y. Nagai, “High performance preparative column chromatography of lipids using a new porous silica, Iatrobeads. I. Separation of molecular species of sphingoglycolipids,” Biochimica et Biophysica Acta, vol. 424, no. 1, pp. 98–105, 1976.
- N. Kanda and S. Watanabe, “Gangliosides GD1b, GT1b, and GQ1b enhance IL-2 and IFN-γ production and suppress IL-4 and IL-5 production in phytohemagglutinin-stimulated human T cells,” Journal of Immunology, vol. 166, no. 1, pp. 72–80, 2001.
- W. A. Ernst, J. Maher, S. Cho et al., “Molecular interaction of CD1b with lipoglycan antigens,” Immunity, vol. 8, no. 3, pp. 331–340, 1998.
- T. Batuwangala, D. Shepherd, S. D. Gadola et al., “The crystal structure of human CD1b with a bound bacterial glycolipid,” Journal of Immunology, vol. 172, no. 4, pp. 2382–2388, 2004.
- M. Gilleron, S. Stenger, Z. Mazorra et al., “Diacylated sulfoglycolipids are novel Mycobacterial antigens stimulating CD1-restricted T cells during infection with Mycobacterium tuberculosis,” Journal of Experimental Medicine, vol. 199, no. 5, pp. 649–659, 2004.
- M. B. Goren, O. Brokl, B. C. Das, and E. Lederer, “Sulfolipid I of Mycobacterium tuberculosis, strain H37RV. Nature of the acyl substituents,” Biochemistry, vol. 10, no. 1, pp. 72–81, 1971.
- J. Guiard, A. Collmann, M. Gilleron et al., “Synthesis of diacylated trehalose sulfates: candidates for a tuberculosis vaccine,” Angewandte Chemie—International Edition, vol. 47, no. 50, pp. 9734–9738, 2008.
- J. Guiard, A. Collmann, L. F. Garcia-Alles et al., “Fatty acyl structures of Mycobacterium tuberculosis sulfoglycolipid govern T cell response,” Journal of Immunology, vol. 182, no. 11, pp. 7030–7037, 2009.
- D. Garzón, P. J. Bond, and J. D. Faraldo-Gómez, “Predicted structural basis for CD1c presentation of mycobacterial branched polyketides and long lipopeptide antigens,” Molecular Immunology, vol. 47, no. 2-3, pp. 253–260, 2009.
- D. B. Moody, T. Ulrichs, W. Mühlecker et al., “CD1c-mediated T-cell recognition of isoprenoid glycolipids in Mycobacterium tuberculosis infection,” Nature, vol. 404, no. 6780, pp. 884–888, 2000.
- J. F. Pennock, F. W. Hemming, and R. A. Morton, “Dolichol: a naturally occurring isoprenoid alcohol,” Nature, vol. 186, no. 4723, pp. 470–472, 1960.
- P. Low, G. Dallner, S. Mayor, S. Cohen, B. T. Chait, and A. K. Menon, “The mevalonate pathway in the bloodstream form of Trypanosoma brucei. Identification of dolichols containing 11 and 12 isoprene residues,” Journal of Biological Chemistry, vol. 266, no. 29, pp. 19250–19257, 1991.
- I. Matsunaga, A. Bhatt, D. C. Young et al., “Mycobacterium tuberculosis pks12 produces a novel polyketide presented by CD1c to T cells,” Journal of Experimental Medicine, vol. 200, no. 12, pp. 1559–1569, 2004.
- A. de Jong, E. C. Arce, T. Y. Cheng et al., “CD1c presentation of synthetic glycolipid antigens with foreign Alkyl branching motifs,” Chemistry and Biology, vol. 14, no. 11, pp. 1232–1242, 2007.
- D. Crich and V. Dudkin, “Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl β-D-mannopyranoside, an unusual β-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis,” Journal of the American Chemical Society, vol. 124, no. 10, pp. 2263–2266, 2002.
- R. P. Van Summeren, D. B. Moody, B. L. Feringa, and A. J. Minnaard, “Total synthesis of enantiopure β-D-mannosyl phosphomycoketides from Mycobacterium tuberculosis,” Journal of the American Chemical Society, vol. 128, no. 14, pp. 4546–4547, 2006.
- K. Hiromatsu, C. C. Dascher, K. P. LeClair et al., “Induction of CD1-restricted immune responses in guinea pigs by immunization with mycobacterial lipid antigens,” Journal of Immunology, vol. 169, no. 1, pp. 330–339, 2002.
- D. M. Zajonc and M. Kronenberg, “CD1 mediated T cell recognition of glycolipids,” Current Opinion in Structural Biology, vol. 17, no. 5, pp. 521–529, 2007.
- D. Qiu and R. R. Schmidt, “Glycosyl imidates, 52. Synthesis of Globotriaosylceramide (Gb3) and Isoglobotriaosylceramide (isoGb3),” Liebigs Annalen der Chemie, vol. 1993, no. 3, pp. 217–224, 1992.
- N. Yin, X. Long, R. D. Goff et al., “Alpha anomers of iGb3 and Gb3 stimulate cytokine production by natural killer T cells,” ACS Chemical Biology, vol. 4, no. 3, pp. 191–197, 2009.
- R. J. Anderson, “The chemistry of the lipoids of tubercle bacilli. XIV. The occurrence of inosite in the phosphatide from human tubercle bacilli,” Journal of the American Chemical Society, vol. 52, no. 4, pp. 1607–1608, 1930.
- C. E. Ballou, E. Vilkas, and E. Lederer, “Structural studies on the myo-inositol phospholipids of Mycobacterium tuberculosis (var. bovis, strain BCG),” Journal of Biological Chemistry, vol. 238, no. 1, pp. 69–76, 1963.
- M. Gilleron, C. Ronet, M. Mempel, B. Monsarrat, G. Gachelin, and G. Puzo, “Acylation state of the phosphatidylinositol mannosides from Mycobacterium bovis Bacillus Calmette Guérin and ability to induce granuloma and recruit natural killer T cells,” Journal of Biological Chemistry, vol. 276, no. 37, pp. 34896–34904, 2001.
- H. De La Salle, S. Mariotti, C. Angenieux et al., “Immunology: assistance of microbial glycolipid antigen processing by CD1e,” Science, vol. 310, no. 5752, pp. 1321–1324, 2005.
- G. D. Ainge, N. A. Parlane, M. Denis et al., “Phosphatidylinositol mannoside ether analogues: ayntheses and interleukin-12-inducing properties,” Journal of Organic Chemistry, vol. 72, no. 14, pp. 5291–5296, 2007.
- X. Liu, B. L. Stocker, and P. H. Seeberger, “Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis,” Journal of the American Chemical Society, vol. 128, no. 11, pp. 3638–3648, 2006.
- T. Natori, Y. Koezuka, and T. Higa, “Agelasphins, novel α-galactosylceramides from the marine sponge Agelas mauritianus,” Tetrahedron Letters, vol. 34, no. 35, pp. 5591–5592, 1993.
- M. Morita, K. Motoki, K. Akimoto et al., “Structure-activity relationship of α-galactosylceramides against b16- bearing mice,” Journal of Medicinal Chemistry, vol. 38, no. 12, pp. 2176–2187, 1995.
- L. Van Kaer, “α-galactosylceramide therapy for autoimmune diseases: prospects and obstacles,” Nature Reviews Immunology, vol. 5, no. 1, pp. 31–42, 2005.
- D. I. Godfrey and S. P. Berzins, “Control points in NKT-cell development,” Nature Reviews Immunology, vol. 7, no. 7, pp. 505–518, 2007.
- G. T. Fan, Y. S. Pan, K. C. Lu et al., “Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes,” Tetrahedron, vol. 61, no. 7, pp. 1855–1862, 2005.
- O. Plettenburg, V. Bodmer-Narkevitch, and C. H. Wong, “Synthesis of α-galactosyl ceramide, a potent immunostimulatory agent,” Journal of Organic Chemistry, vol. 67, no. 13, pp. 4559–4564, 2002.
- D. Wu, M. Fujio, and C. H. Wong, “Glycolipids as immunostimulating agents,” Bioorganic and Medicinal Chemistry, vol. 16, no. 3, pp. 1073–1083, 2008.
- C. Angénieux, V. Fraisier, B. Maître et al., “The cellular pathway of CD1e in immature and maturing dendritic cells,” Traffic, vol. 6, no. 4, pp. 286–302, 2005.