Facile solid phase synthesis of YEE(ah-GalNAc)3, a ligand with known high affinity for the asialoglycoprotein receptor

Synlett

Volumn , Issue 6, 2000, Pages 797-800

  Jiaang, Weir Torn ^a   Tseng, Ping Hui ^a   Chen, Shui Tein ^a  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

Asialoglycoprotein receptor; Cluster glycoside; Ligand; Oxazoline; Solid phase

Indexed keywords

ASIALOGLYCOPROTEIN RECEPTOR; GLYCOSIDE; LIGAND; OXAZOLINE DERIVATIVE; SUCCINIC ACID;

ARTICLE; BINDING AFFINITY; DRUG SOLUBILITY; DRUG SYNTHESIS; LIGAND BINDING; LIVER; NONHUMAN; RECEPTOR BINDING; SOLID PHASE EXTRACTION;

EID: 0034047792     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. (a) Ashwell, G.; Harford, J. Annu. Rev. Biochem. 1982, 51, 531-554.
2. (b) Schwartz, A. L. CRC Crit. Rev. Biochem. 1984, 16, 207-233.
3. (a) Lee, Y. C. FASEB J. 1992, 6, 3193-3200.
4. (b) Lee, R. T.; Lee, Y. C. Biochem. Biophvs. Res. Commun. 1988, 155, 1444-1451.
5. (c) Lee, R. T.; Lin, P.; Lee, Y. C. Biochemistry 1984, 23, 4255-4261.
6. (a) Findeis, M. A. Int. J. Peptide. Res. 1994, 43, 477-485.
7. (b) Arnarp, J.; Haraldsson, M.; Lonngren, J. J. Chem. Soc., Perkin Trans. I 1982, 1841-1844 and references therein.
8. Lee, R. T.; Lee, Y. C. Bioconjugate Chem. 1997, 8, 762-765.
9. Lee, R. T.; Lee, Y. C. Glycoconjugate J. 1987, 4, 317-328.
10. (a) Findeis, M. A.; Merwin, J. R.; Spitalny, G. L.; Chiou, H. C. Trends Biotechnol. 1993, 11, 202-205.
11. (b) Wu. G. Y.; Wu, C. H. J. Biol. Chem. 1988, 263, 14621-14624.
12. (c) Wu. G. Y.; Wu, C. H. in Liver Diseases: Targeted Diagnosis and Therupy Using Specific Receptors and Ligands; Marcel Dekker: New York, 1991; p 127-149.
13. (d) Merwin, J. R.; Noell, G. S.; Thomas, W. L.; Chiou, H. C.; DeRome, M. E.; McKee, T. D.; Spitalny, G. L.; Findeis, M. A. Bioconjugate Chem. 1994, 5, 612.
14. (a) Wu, G. Y.; Wu, C. H. J. Biol. Chem. 1992, 267, 12436-12439.
15. (b) Hangeland, J. J.; Levis, J. T.; Lee, Y. C.; Ts'o, P. O. P. Bioconjugate Chem. 1995, 6, 695-701.
16. Lee, R. T.; Wong, T. C.; Lee, Y. C. J. Carbohydr. Chem. 1986, 5, 343-357.
17. (a) Nakabayashi, S.; Warren, C. D.; Jeanloz, R. W. Carbohydr. Res. 1986, 150, C7-C10.
18. (b) Nakabayashi, S.; Warren, C. D.; Jeanloz, R. W. Carbohydr. Res. 1988, 174, 279-289.
19. Yule, J. E.; Wong, T. C.; Gandhi, S. S.; Qiu, D.; Riopel, M. A.; Koganty, R. R. Tetrahedron Lett. 1995, 36, 6839-6842.
20. Horrobin, T.; Tran, C. H.; Crout, D. J. Chem. Soc., Perkin Trans. I 1998, 1069-1080. Horrobin et al reported that tetraacetate 8 was regioselective 6-deacetylation by the esterase-catalysed hydrolysis, gave the 6-hydroxy derivative 9 in 73% yield. We believed that treatment of compound 9 and benzyl succinate acid with DCC, 4-DMAP would afford compound 4 in excellent yield. The approach of enzymatic method offers a concise strategy to synthesize 4, it is unfortunate that the source of esterase (from R. toruloides) is not commerically available.
21. Handa, V. K.; Barlow, J. J.; Matta, H. L. Carbohydr. Res. 1979, 76, C10-C13.
22. ++1, 100), 478.2 (29).
23. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334, see reference 6.
24. Yamada, K.; Nishimura, S.-I. Tetrahedron Lett. 1995, 36, 9493-9496.
25. ++1, 100), 330 (23), 469.2 (9).
26. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
27. (a) Coste, J.; Dutour, M. N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 31, 205-208.
28. (b) Høeg-Jansen, T. Tetrahedron Lett. 1991, 32, 7617-7620.
29. (a) Marks, W. H.; Ma, Y.; Yirdaw, G.; Florence, L. Transplantation 1997, 63, 293-298.
30. (b) Treichel, U.; Meyerzum-Buschenfelde, K. H.; Dienes, H. P.; Gerken, G. Arch. Virol. 1997, 142, 493-498.
31. (c) Kawakami, S.; Yamashita, F.; Nishikawa, M.; Takakura, Y.; Hashida, M. Biochem. Biophys. Res. Commun. 1998, 252, 78-83.