Carbohydrate-derived small-molecule libraries

Combinatorial Synthesis of Natural Product-Based Libraries

Volumn , Issue , 2006, Pages 165-184

  Boldi, Armen M ^a  

^a Codexis Inc ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85056028335     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420009279     Document Type: Chapter

References (73)

1. Hirschmann, R., Ducry, L., and Smith, A.B., III, Development of an efficient, regio-, and stereoselective route to libraries based on the β-D-glucose scaffold, J. Org. Chem., 65, 8307, 2000.
2. Witczak, Z.J. and Tatsuta, K. (Eds.), Carbohydrate synthons in natural products chemistry: synthesis, functionalization, and applications, American Chemical Society, Washington, D.C., 2003.
3. Hollingsworth, R.I. and Wang, G., Toward a carbohydrate-based chemistry: progress in the development of general-purpose chiral synthons from carbohydrates, Chem. Rev., 100, 4267, 2000.
4. Musser, J.H., Carbohydrate-based therapeutics, in Burger’s Medicinal Chemistry and Drug Discovery, Vol. 2, Abraham, D.J., Ed., John Wiley & Sons, New York, 2003, chap. 7.
5. Hegde, S. and Carter, J., To market, to market-2003, Annu. Rep. Med. Chem., 39, 337, 2004.
6. Maryanoff, B.E. et al., Structure-activity studies on anticonvulsant sugar sulfamates related to topiramate. Enhanced potency with cyclic sulfate derivatives, J. Med. Chem., 41, 1315, 1998.
7. Oxford, J.S., Zanamivir (Glaxo Wellcome), IDrugs, 3, 447, 2000.
8. Stavenger, R.A. and Schreiber, S.L., Asymmetric catalysis in diversity-oriented organic synthesis:enantioselective synthesis of 4320 encoded and spatially segregated dihydropyrancarboxamides, Angew. Chem., Int. Ed. Engl., 40, 3417, 2001.
9. Dube, D.H. and Bertozzi, C.R., Glycans in cancer and inflammation - potential for therapeutics and diagnostics, Nat. Rev. Drug Discovery, 4, 477, 2005.
10. Shriver, Z., Raguram, S., and Sasisekharan, R., Glycomics: a pathway to a class of new and improved therapeutics, Nat. Rev. Drug Discovery, 3, 863, 2004.
11. Bertozzi, C.R. and Kiessling, L.L., Chemical glycobiology, Science, 291, 2357, 2001.
12. Dwek, R.A., Glycobiology: toward understanding the function of sugars, Chem. Rev., 96, 683, 1996.
13. Gruner, S.A.W. et al., Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds, Chem. Rev., 102, 491, 2002.
14. Frechét, J.M. and Schuerch, C., Solid-phase synthesis of oligosaccharides. I. Preparation of the solidsupport. Poly [p-1-propen-3-ol-1-yl)styrene], J. Am. Chem. Soc., 93, 492, 1971.
15. Hölemann, A. and Seeberger, P.H., Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates, Curr. Opin. Biotech., 15, 615, 2004.
16. Ohnsmann, J., Madalinksi, M., and Kunz, H., Carbohydrates as polyfunctional scaffolds in combinatorial synthesis, Chimica Oggi, 20, 2005.
17. Marcaurelle, L.A. and Seeberger, P.H., Combinatorial carbohydrate chemistry, Curr. Opin. Chem. Biol., 6, 289, 2002.
18. Seeberger, P.H., Ed., Solid-Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries, John Wiley & Sons, New York, 2001.
19. Nishimura, S., Combinatorial syntheses of sugar derivatives, Curr. Opin. Chem. Biol., 5, 325, 2001.
20. Seeberger, P.H. and Haase, W.-C., Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries, Chem. Rev., 100, 4349, 2000.
21. Schweizer, F. and Hindsgaul, O., Combinatorial synthesis of carbohydrates, Curr. Opin. Chem. Biol., 3, 291, 1999.
22. Sofia, M.J. and Silva, D.J., Recent developments in solid-and solution-phase methods for generating carbohydrate libraries, Curr. Opin. Drug Discovery Dev., 2, 365, 1999.
23. Kahne, D., Combinatorial approaches to carbohydrates, Curr. Opin. Chem. Biol., 1, 130, 1997.
24. Evans, B.E. et al., Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists, J. Med. Chem., 31, 2235, 1988.
25. Hirschmann, R. et al., De novo design and synthesis of somatostatin non-peptide peptidomimetics utilizing β-D-glucose as a novel scaffolding, J. Am. Chem. Soc., 115, 12550, 1993.
26. Hirschmann, R. et al., Synthesis of potent cyclic hexapeptide NK-1 antagonists. Use of a mini-library in transforming a peptidal somatostatin receptor ligand into an NK-1 receptor ligand via a polyvalent peptidomimetic, J. Med. Chem., 39, 2441, 1996.
27. Hirschmann, R. et al., Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity: a new route to ether synthesis, J. Med. Chem., 41, 1382, 1998.
28. Prasad, V. et al., Effects of heterocyclic aromatic substituents on binding affinities at two distinct sites of somatostain receptors. Correlation with the electrostatic potential of the substituents, J. Med. Chem., 46, 1858, 2003.
29. For other examples, see (a) Papageorgiou, C. et al., Bioorg. Med Chem. Lett., 2, 135, 1992.
30. Nicolaou, K.C., Trujillo, J.I., and Chibale, K., Tetrahedron, 53, 8751, 1997.
31. Diguarher, T.L. et al., Bioorg. Med. Chem. Lett., 6, 1983, 1996.
32. McDevitt, J.P. and Lansbury, P.T., Jr., Glycosamino acids: new building blocks for combinatorial synthesis, J. Am. Chem. Soc., 118, 3818, 1996.
33. Sofia, M.J. et al., Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries, J. Org. Chem., 63, 2802, 1998.
34. Murphy, P.V. et al., Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds, Tetrahedron, 59, 2259, 2003.
35. Chery, F. et al., Synthesis of peptidomimetics based on iminosugard and β-D-glucopyranoside scaffolds and inhibition of HIV-protease, Tetrahedron, 60, 6597, 2004.
36. Wunberg, T. et al., Carbohydrates as multifunctional chiral scaffolds in combinatorial synthesis, Angew. Chem., Int. Ed. Engl., 37, 2503, 1998.
37. Kallus, C. et al., Tetrahedron Lett., 40, 7783, 1999.
38. Opatz, T. et al., D-Glucose as a pentavalent chiral scaffold, Eur. J. Org. Chem., 1527, 2003.
39. Opatz, T. et al., Carbohydrate Res., 337, 2089, 2002.
40. Boer, J. et al., Design, synthesis, and biological evaluation of α4β1 integrin antagonists based on β-D-mannose as rigid scaffold, Angew. Chem., Int. Ed. Engl., 40, 3870, 2001.
41. Wong, C.-H. et al., A library approach to the discovery of small molecules that recognize RNA: use of a 1,3-hydroxyamine motif as core, J. Am. Chem. Soc., 120, 8319, 1998.
42. Messer, R., Fuhrer, C.A., and Häner, R., Natural product-like libraries based on non-aromatic, polycyclic motifs, Curr. Opin. Chem. Biol., 9, 259, 2005.
43. Kim, Y.-K. et al., Relationship of stereochemical and skeletal diversity of small molecules to cellular measurement space, J. Am. Chem. Soc., 126, 14740, 2004.
44. Timmer, M.S.M. et al., The use of a mannitol-derived fused oxacycle as a combinatorial scaffold, J. Org. Chem., 68, 9406, 2003.
45. Kubota, H., Lim, J., Depew, K.M., and Schreiber, S.L., Pathway development and pilot library realization in diversity-oriented synthesis: exploring Ferrier and Pauson-Khand reactions on a glycal template, Chem. Biol., 9, 265, 2002.
46. Hotha, S. and Tripathi, A., Diversity oriented synthesis of tricyclic compounds from glycals using the Ferrier and the Pauson-Khand reactions, J. Comb. Chem., 7, 968, 2005.
47. Burke, M.D., Berger, E.M., and Schreiber, S.L., A synthesis strategy yielding skeletally diverse small molecules combinatorially, J. Am. Chem. Soc., 126, 14095, 2004.
48. Burke, M.D. and Schreiber, S.L., A planning strategy for diversity-oriented synthesis, Angew. Chem., Int. Ed. Engl., 43, 46, 2004.
49. Schreiber S.L., Target-oriented and diversity-oriented organic synthesis in drug discovery, Science, 287, 1964, 2000.
50. Buckingham, J., Dictionary of Natural Products, Taylor and Francis/CRC Press, London, 2005 (CDROM).
51. Omura, S., Ed., Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd ed., Academic Press, San Diego, CA, 2002.
52. Haag, R. et al., New polyethylene glycol polymers as ketal protecting groups - a polymer supported approach to symmetrically substituted spiroketals, Synth. Commun., 31, 2965, 2001.
53. Barun, O., Sommer, S., and Waldmann, H., Asymmetric solid-phase synthesis of 6,6-spiroketals, Angew. Chem., Int. Ed. Engl., 43, 3195, 2004.
54. Paterson, I., Gottschling, D., and Menche, D., Towards the combinatorial synthesis of spongistatin fragment libraries by using asymmetric aldol reactions on solid-support, Chem. Commun., 3568, 2005.
55. Kulkarni, B.A. et al., Combinatorial synthesis of natural product-like molecules using a first-generation spiroketal scaffold, J. Comb. Chem., 4, 56, 2002.
56. Walters, M.A. et al., Templates for exploratory library preparation. Derivatization of a functionalized spirocyclic 3,6-dihydro-2H-pyran formed by ring-closing metathesis reaction, J. Comb. Chem., 4, 125, 2002.
57. Lichtenthaler, F.W., Enantiopure building blocks from sugars and their utilization in natural product synthesis, in Modern Synthetic Methods, Scheffold, R., Ed., VCH, New York, 1992, pp. 273-376.
58. Hollingsworth, R.I. and Wang, G., Chem. Rev., 100, 4267, 2000.
59. Chauhan, P.M.S., Drugs Future, 25, 481, 2000.
60. Prous, J.R., Ed., Drugs Future, 25, 402, 2000.
61. Edwards, A.A. et al., Tetrahydrofuran-based amino acids as library scaffolds, J. Comb. Chem., 6, 230, 2004.
62. Krueger, E.B. et al., Solution-phase library synthesis of furanoses, J. Comb. Chem., 4, 229, 2002.
63. Boldi, A.M. et al., Aminofuranose Compounds, U.S. Patent 6,794,497, September 21, 2004.
64. Boldi, A.M., Building discovery libraries from natural products, ACS Prospectives Conference on Combinatorial Chemistry: New Methods, New Discoveries, September 21-24, 2003.
65. Krueger, E.B., Hu, C., and Boldi, A.M., unpublished results.
66. Ejjiya, S., Saluzzo, C., and Amouroux, R., O4, O5-Isopropylidene-1,2:3,6-dianhydro-D-glucitol from isosorbide, Org. Synth., 77, 91, 1999.
67. Duggan, M.E. and Imagire, J.S., Copper(I) chloride catalyzed addition of alcohols to alkyl isocyanates, A mild and expedient method for alkyl carbamate formation, Synthesis, 131, 1989.
68. Ohe, K. et al., A facile preparation of 4-alkylidene-3-tosyloxazolidin-2-ones from propargylic alcohols and p-toluenesulfonyl isocyanate using a cuprous iodide/triethylamine catalyst, J. Org. Chem., 56, 2267, 1991.
69. Boldi, A.M., Libraries containing natural product structural motifs, CHI 6th Annual Conference on High-Throughput Organic Synthesis, San Diego, CA, February 14-16, 2001.
70. Boldi, A.M., Libraries containing natural product Structural Motifs, CHI 5th Annual Conference on Drug Discovery Japan, Tokyo, Japan, March 27-29, 2001.
71. Eissa, H.O. and Boldi, A.M., unpublished results.
72. Adams, J.H. et al., A reinvestigation of the preparation, properties, and applications of aminomethyl and 4-methylbenzhydrylamine polystyrene resins, J. Org. Chem., 63, 3706, 1998.
73. Szardenings, A.K. et al., A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines, J. Org. Chem., 61, 6720, 1996.