Toward the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks

Tetrahedron

Volumn 66, Issue 22, 2010, Pages 3951-3962

  Saito, Akihiro ^a   Wakao, Masahiro ^a   Deguchi, Hiroshi ^a   Mawatari, Aya ^a   Sobel, Michael ^b   Suda, Yasuo ^a,c  

^a KAGOSHIMA UNIVERSITY   (Japan)

^b VA PUGET SOUND HEALTH CARE SYSTEM   (United States)

^c SUDx Biotec Corporation   (Japan)

Author keywords

Glucosamine; Glucuronic acid; Heparan sulfate; Heparin; Iduronic acid; Synthesis; Uronic acid

Indexed keywords

DISACCHARIDE; GLUCOSAMINE; GLUCURONIC ACID; HEPARAN SULFATE; HEPARIN; IDURONIC ACID; LACTONE; MONOSACCHARIDE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DEPROTECTION REACTION; GLYCOSYLATION; OXIDATION; PRIORITY JOURNAL; SULFATION;

EID: 77953123854     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.077     Document Type: Article

References (61)

1. In: Garg H.G., Linhardt R.J., and Hales C.A. (Eds). Chemistry and Biology of Heparin and Heparan Sulfate (2005), Elsevier, Amsterdam, The Netherlands
2. Conrad H.E. Heparin-Binding Proteins (1998), Academic, San Diego, CA, USA
3. Imberty A., Lortat-Jacob H., and Pérez S. Carbohydr. Res. 342 (2007) 430-439
4. Raman R., Sasisekharan V., and Sasisekharan R. Chem. Biol. 12 (2005) 267-277
5. Coombe D.R., and Kett W.C. Cell. Mol. Life Sci. 62 (2005) 410-424
6. Petitou M., and van Boeckel C.A.A. Angew. Chem., Int. Ed. 43 (2004) 3118-3133
7. Rabenstein D.A. Nat. Prod. Rep. 19 (2002) 312-331
8. Capila I., and Linhardt R.J. Angew. Chem., Int. Ed. 41 (2002) 390-412
9. Turnbull J., Powell A., and Guimond S. Trends Cell Biol. 11 (2001) 75-82
10. Casu B., and Lindahl U. Adv. Carbohydr. Chem. Biochem. 57 (2001) 159-206
11. Esko J.D., and Lindahl U. J. Clin. Invest. 108 (2001) 169-173
12. Bernfield M., Götte M., Park P.W., Reizes O., Fitzgerald M.L., Lincecum J., and Zako M. Annu. Rev. Biochem. 68 (1999) 729-777
13. For comprehensive reviews on the synthesis of GAGs, see:
14. Noti C., and Seeberger P.H. Chem. Biol. 12 (2005) 731-756
15. Karst N.A., and Linhardt R.J. Curr. Med. Chem. 10 (2003) 1993-2031
16. Poletti L., and Lay L. Eur. J. Org. Chem. (2003) 2999-3024
17. Yeung B.K.S., Chong P.Y.C., and Petillo P.A. J. Carbohydr. Chem. 21 (2002) 799-865
18. Tamura J. Trends Glycosci. Glycotechnol. 13 (2001) 65-88
19. For recent articles on the synthesis of GAGs see:
20. Polat T., and Wong C.H. J. Am. Chem. Soc. 129 (2007) 12795-12800
21. Zhou Y., Lin F., Chen J., and Yu B. Carbohydr. Res. 341 (2006) 1619-1629
22. Noti C., de Paz J.L., Polito L., and Seeberger P.H. Chem.-Eur. J. 12 (2006) 8664-8686
23. de Paz J.L., Noti C., and Seeberger P.H. J. Am. Chem. Soc. 128 (2006) 2766-2767
24. Gama C.I., Tully S.E., Sotogaku N., Clark P.M., Rawat M., Vaidehi N., Goddard W.A., Nishi A., and Hsieh-Wilson L.C. Nat. Chem. Biol. 2 (2006) 467-473
25. Codée J.D.C., Stubba B., Schiattarella M., Overkleeft H.S., van Boeckel C.A.A., van Boom J.H., and van der Marel G.A. J. Am. Chem. Soc. 127 (2005) 3767-3773
26. Lee J.C., Lu X.A., Kulkarni S.S., Wen Y.S., and Hung S.C. J. Am. Chem. Soc. 126 (2004) 476-477
27. Orgueira H.A., Bartolozzi A., Schell P., Litjens R.E., Palmacci E.R., and Seeberger P.H. Chem.-Eur. J. 9 (2003) 140-169
28. de Paz J.L., Ojeda R., Reichadt, and Martín-Lomas M. Eur. J. Org. Chem. (2003) 3308-3324
29. Kovensky J., Mallet J.M., Esnault J., Driguez P.A., Sizun P., Hérault J.P., Herbert J.M., Petitou M., and Sinaÿ P. Eur. J. Org. Chem. (2002) 3595-3603
30. de Paz J.L., Angulo J., Lassaletta J.M., Nieto P.M., Redondo-Horcajo M., Lozano R.M., Gimenez-Gallego G., and Martin-Lomas M. ChemBioChem 2 (2001) 673-685 and references cited therein
31. For recent articles on HP/HS oligosaccharide library, see:
32. Hecht M.L., Rosental B., Horlacher T., Hershkovitz O., de Paz J.L., Noti C., Schauer S., Porgador A., and Seeberger P. J. Proteome Res. 8 (2009) 712-720
33. Herczeg M., Lázár L., Borbás A., Lipták A., and Antus S. Org. Lett. 11 (2009) 2619-2622
34. Dilhas A., Lucas R., Loureiro-Morais L., Hersant Y., and Bonnaffé D. J. Comb. Chem. 10 (2008) 166-169
35. de Paz J.L., Moseman E.A., Noti C., Polito L., von Andrian U.H., and Seeberger P.J. ACS Chem. Biol. 2 (2007) 735-744
36. Lu L.-D., Shie C.-R., Kulkarni S.S., Pan G.-R., Lu X.-A., and Hung S.-C. Org. Lett. 8 (2006) 5995-5998
37. Fan R.-H., Achkar J., Hernándes-Torres J.M., and Wei A. Org. Lett. 7 (2005) 5095-5098
38. For our previous studies, see:
39. Wakao M., Saito A., Ohishi K., Kishimoto Y., Nishimura T., Sobel M., and Suda Y. Bioorg. Med. Chem. Lett. 18 (2008) 2499-2504
40. Suda Y., Arano A., Fukui Y., Koshida S., Wakao M., Nishimura T., Kusumoto S., and Sobel M. Bioconjugate Chem. 17 (2006) 1125-1135
41. Koshida S., Suda Y., Sobel M., and Kusumoto S. Tetrahedron Lett. 42 (2001) 1289-1292
42. Koshida S., Suda Y., Fukui Y., Ormsby J., Sobel M., and Kusumoto S. Tetrahedron Lett. 40 (1999) 5725-5728
43. Suda Y., Bird K., Shiyama T., Koshida S., Marques D., Fukase K., Sobel M., and Kusumoto S. Tetrahedron Lett. 37 (1996) 1053-1056
44. For articles on the synthesis of uronic acids moieties, see:
45. Hansen S.U., Baráth M., Salameh B.A.B., Pritchard R.G., Stimpson W.T., Gardiner J.M., and Jayson G.C. Org. Lett. 11 (2009) 4528-4531
46. Tatai J., Osztrovszky G., Kajtár-Peredy M., and Fügedi P. Carbohydr. Res. 343 (2008) 596-606
47. Hassan H.H.A.M. Mini-Rev. Org. Chem. 4 (2007) 61-74
48. Lohman G.J.S., Hunt D.K., Högermeier J.A., and Seeberger P.H. J. Org. Chem. 68 (2003) 7559-7561
49. Ke W., Whitfield D.M., Gill M., Larocque S., and Yu S.-H. Tetrahedron Lett. 44 (2003) 7767-7770
50. Barroca N., and Jacquinet J.-C. Carbohydr. Res. 329 (2000) 667-679
51. Lubineau A., Alais G.J., and Bonnaffé D. Tetrahedron Lett. 41 (2000) 307-311
52. Ojeda R., de Paz J.L., Martin-Lomas M., and Lassaletta J.M. Synlett (1999) 1316-1318
53. Hinou H., Kurosawa H., Matsuoka K., Terunuma D., and Kuzuhara H. Tetrahedron Lett. 40 (1999) 1501-1504
54. Rochepeau-Jobron L., and Jacquinet J.-C. Carbohydr. Res. 303 (1997) 395-406
55. Medakovic D. Carbohydr. Res. 253 (1994) 299-300
56. Jacquinet J.-C., Petitou M., Duchaussoy P., Lederman I., Choay J., Torri G., and Sinaÿ P. Carbohydr. Res. 130 (1984) 221-241
57. Czuk R., Hoenig H., Nimpf J., and Weidmann H. Tetrahedron Lett. 21 (1980) 2135-2136
58. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley & Sons,, New York, NY
59. A trace amount of furanose form was observed by NMR analysis.
60. Alper P.B., Hung S.-C., and Wong C.-H. Tetrahedron Lett. 37 (1996) 6029-6032
61. α-Selective glycosylation with 2-azido imidate in the presence of TBDMSOTf was previously reported, see:. Kovensky J., Duchaussoy P., Petitou M., and Sinaÿ P. Tetrahedron: Asymmetry 7 (1996) 3119-3128