Solid phase lipid synthesis (SPLS) for construction of an artificial glycolipid library

Chemical Communications

Volumn , Issue 14, 2000, Pages 1281-1282

  Hamachi, Itaru ^a,b   Kiyonaka, Shigeki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOLIPID; LIPID;

ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; LIPOGENESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0034698228     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002545n     Document Type: Article

References (19)

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2. S. Hakomori, Annu. Rev. Biochem., 1981, 50, 733; S. Hakomori, Pure Appl. Chem., 1991, 63, 473; A. Varki, Glycobiology, 1993, 3, 97; R. A. Dwek, Chem. Rev., 1996, 96, 683; K. J. Yarema and C. R. Bertozzi, Curr. Opin. Chem. Biol., 1998, 2, 49.
3. S. Hakomori, Annu. Rev. Biochem., 1981, 50, 733; S. Hakomori, Pure Appl. Chem., 1991, 63, 473; A. Varki, Glycobiology, 1993, 3, 97; R. A. Dwek, Chem. Rev., 1996, 96, 683; K. J. Yarema and C. R. Bertozzi, Curr. Opin. Chem. Biol., 1998, 2, 49.
4. S. Hakomori, Annu. Rev. Biochem., 1981, 50, 733; S. Hakomori, Pure Appl. Chem., 1991, 63, 473; A. Varki, Glycobiology, 1993, 3, 97; R. A. Dwek, Chem. Rev., 1996, 96, 683; K. J. Yarema and C. R. Bertozzi, Curr. Opin. Chem. Biol., 1998, 2, 49.
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6. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
7. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
8. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
9. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
10. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
11. Several types of artificial glycolipids have been prepared recently: M. Hato and H. Minamikawa, Langmuir, 1996, 12, 1658; Z. Zhang, K. Kukunaga, Y. Sugimura, K. Nakao and T. Shimizu, Carbohydr. Res., 1996, 292, 47; Y. Hisaeda, E. Ohshima, J. Kikuchi and Y. Murakami, Tetrahedron Lett., 1997, 38, 6713; S. Takeoka, K. Sou, C. Boettcher, J. H. Fuhrhop and E. Tsuchida, J. Chem. Soc., Faraday Trans., 1998, 94, 2151; J. Song and R. I. Hollingsworth, J. Am. Chem. Soc., 1999, 121, 1851; H. C. Hansen and G. Magnusson, Carbohydr. Res., 1999, 322, 181.
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19. 1H NMR spectra of the final products obtained by hydrazinolysis suggest that the glycolipids were partially racemized at the connector site (8/2 = L-asp/D-asp).