Oligosaccharide synthesis by affinity separation based on molecular recognition between podand ether and ammonium ion

Synlett

Volumn , Issue 15, 2005, Pages 2342-2346

  Fukase, Koichi ^a   Takashina, Mamoru ^a   Hori, Yumiko ^a   Tanaka, Daizo ^a   Tanaka, Katsunori ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Affinity separation; Glycosylation; High throughput synthesis; Linker; Oligosaccharide synthesis

Indexed keywords

AMMONIA; ETHER; MONOSACCHARIDE; OLIGOSACCHARIDE;

ARTICLE; FLOW MEASUREMENT; GLYCOSYLATION; MOLECULAR RECOGNITION; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 25444519769     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872269     Document Type: Article

References (24)

1. (a) Zhang, W. Curr. Opin. Drug Discov. Dev. 2004, 7, 784.
2. (b) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693.
3. (c) Curran, D. P. Pure Appl. Chem. 2000, 72, 1649.
4. (d) Porco, J. A. Jr. Comb. Chem. High Throughput Screening 2000, 3, 93.
5. Zhang, S.-Q.; Fukase, K.; Kusumoto, S. Tetrahedron Lett. 1999, 40, 7479.
6. Zhang, S.-Q.; Fukase, K.; Izumi, M.; Fukase, Y.; Kusumoto, S. Synlett 2001, 590.
7. Fukase, Y.; Zhang, S.-Q.; Iseki, K.; Oikawa, M.; Fukase, K.; Kusumoto, S. Synlett 2001, 1693.
8. Fukase, K.; Zhang, S.-Q.; Fukase, Y.; Umesakao, N.; Kusumoto, S. In New Discoveries in Agrochemicals; Clark, J. M.; Ohkawa, H., Eds.; ACS Symposium Series 892, American Chemical Society: Washington DC, 2005, 87-98.
9. The podand tag with a shorter chain length showed weaker affinity to the ammonium ion column, whereas the tag having longer chain length, such as 6, showed comparable affinity with the corresponding crown ether derivatives.
10. 2.
11. Fukase, K.; Tanaka, H.; Torii, S.; Kusumoto, S. Tetrahedron Lett. 1990, 31, 389.
12. Fukase, K.; Yoshimura, T.; Hashida, M.; Kusumoto, S. Tetrahedron Lett. 1991, 32, 4019.
13. Fukase, K.; Yasukochi, T.; Nakai, Y.; Kusumoto, S. Tetrahedron Lett. 1996, 37, 3343.
14. Fukase, K.; Nakai, Y.; Egusa, K.; Porco, J. A.; Kusumoto, S. Synlett 1999, 1074.
15. Falb, F.; Yechezkel, T.; Salitra, Y.; Gilon, C. J. Peptide Res. 1999, 53, 507.
16. Benzylcarbonyl and benzyl-type tags can be removed by catalytic hydrogenolysis using Pd catalyst.
17. Egusa, K.; Fukase, K.; Kusumoto, S. Synlett 1997, 675.
18. Yasukochi, T.; Fukase, K.; Kusumoto, S. Tetrahedron Lett. 1999, 40, 6591.
19. α-Selective glycosylation in CPME: Tokimoto, H.; Fujimoto, Y.; Fukase, K.; Kusumoto, S. Tetrahedron: Asymmetry 2005, 16, 441.
20. Glycosylation with nitropyridyl glycoside gave better results than with glycosyl fluoride and thioglycoside. The fucosylation stopped at 50% consumption of 33. The reaction mixture was applied to SAS to give a mixture of 33 and trisaccharide 35. After TFA was removed by liquid-liquid separation, the mixture was subjected to glycosylation with fucosyl donor 34, again. This procedure was repeated twice and the resulting compound 35 was finally purified by silica gel chromatography.
21. Pennemann, H.; Hessel, V.; Loewe, H. Chem. Eng. Sci. 2004, 59, 4789.
22. Jahnisch, K.; Hessel, V.; Loewe, H.; Baerns, M. Angew. Chem. Int. Ed. 2004, 43, 406.
23. Ratner, D. M.; Murphy, E. R.; Jhunjhunwala, M.; Snyder, D. A.; Jensen, K. F.; Seeberger, P. H. Chem. Commun. 2005, 578.
24. IMM micromixer: http://www.imm-main2.de/.