Synthesis on soluble polymers: New reactions and the construction of small molecules

Current Opinion in Chemical Biology

Volumn 1, Issue 1, 1997, Pages 107-113

  Gravert, Dennis J ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OLIGONUCLEOTIDE; OLIGOSACCHARIDE; PEPTIDE LIBRARY; POLYMER;

CHEMISTRY; REVIEW; SYNTHESIS;

INDICATORS AND REAGENTS; OLIGONUCLEOTIDES; OLIGOSACCHARIDES; PEPTIDE LIBRARY; POLYMERS;

EID: 0031152154     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/s1367-5931(97)80116-0     Document Type: Article

References (46)

1. Gravert DJ, Janda KD: Developing small-molecule libraries for drug discovery. Trends Biotechnol 1996, 14:110-112.
2. Mutter M, Bayer E: The liquid-phase method for peptide synthesis. In The Peptides, vol 2. Edited by Gross E, Meienhofer J. New York: Academic Press; 1979:285-332.
3. Geckeler K, Pillai VNR, Mutter M: Applications of soluble polymeric supports. Adv Polym Sci 1980, 39:65-94.
4. Pillai VNR, Mutter M: New perspectives in polymer-supported peptide synthesis. In Topics in Current Chemistry, vol 106. Edited by Boschke FL. New York: Springer-Verlag; 1986:119-175.
5. Geckeler KE: Soluble polymer supports for liquid-phase synthesis. Adv Polym Sci 1995, 121:31-79. This recent review discusses the general features of synthesis on soluble polymers and evaluates their use in peptide and oligonucleotide synthesis.
6. Gravert D, Janda K: Organic synthesis on soluble polymer supports: liquid-phase methodologies. Chem Rev 1997, in press. This review provides a comprehensive survey of peptide, oligonucleotide, oligosaccharide, and small molecule syntheses on soluble polymer supports.
7. Merrifield RB: Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 1963, 85:2149-2154.
8. Shemyakin MM, Ovchinnikov YuA, Kiryushkin AA, Kozhevnikova IV: Synthesis of peptides in solution on a polymeric support I. Synthesis of glycylglycyl-L-leucylglycine. Tetrahedron Lett 1965:2323-2327.
9. Cramer F, Helbig R, Hettler H, Scheit KH, Seliger H: Oligonucleotide synthesis with a soluble polymer as carrier. Angew Chem Int Ed 1966, 5:601.
10. Hayatsu H, Khorana HG: Deoxyribooligonucleotide synthesis on a polymer support. J Am Chem Soc 1966, 88:3182-3183.
11. Guthrie RD, Jenkins AD, Stehlicek J: Synthesis of oligosaccharides on polymer supports. Part I. 6-O-(p-vinylbenzoyl) derivatives of glycopyranose and their copolymers with styrene. J Chem Soc 1971:2690-2696.
12. Harris JM: Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications. Edited by Harris JM. New York: Plenum Press; 1992.
13. Douglas SP, Whitfield DM, Krepinsky JJ: Polymer-supported solution synthesis of oligosaccharides. J Am Chem Soc 1991, 113:5095-5097.
14. Han H, Wolfe MM, Brenner S, Janda KD: Liquid-phase combinatorial synthesis. Proc Natl Acad Sci USA 1995, 92:6419-6423. Combinatorial chemistry on soluble polymers is demonstrated through the construction of a library of sulfonamides and the synthesis and screening of a peptide library.
15. Erb E, Janda KD, Brenner S: Recursive deconvolution of combinatorial chemical libraries. Proc Natl Acad Sci USA 1994, 91:11422-11426.
16. Seliger H, Göldner E, Kittel I, Plage B, Schulten H-R: Two-carrier liquid-phase synthesis of main-chain liquid crystalline oligomers and characterization of the products. Fresenius J Anal Chem 1995, 351:260-270.
17. Han H, Janda KD: Azatides: solution and liquid phase synthesis of a new peptidomimetic. J Am Chem Soc 1996, 118:2539-2544.
18. Bonora GM: Use of polyethylene glycol (PEG) as a soluble polymeric support in the oligonucleotide synthesis. A proposal for a new liquid-phase method. Gazz Chim Ital 1987, 117:379-380.
19. Colonna FP, Scremin CL, Bonora GM: Large scale H.EL.P. synthesis of oligodeoxynucleotides by the hydroxybenzotriazole phosphotriester approach. Tetrahedron Lett 1991, 32:3251-3254.
20. Bonora GM, Biancotto G, Maffini M, Scremin CL: Large scale, liquid-phase synthesis of oligonucleotides by the phosphoramidite approach. Nucleic Acids Res 1993, 21:1213-1217.
21. Bonora GM: Polyethylene glycol. A high-efficiency liquid-phase (HELP) for the large-scale synthesis of the oligonucleotides. Appl Biochem Biotechnol 1995, 54:3-17. This paper describes the various HELP methods of oligonucleotide synthesis and includes a discussion of advantages and disadvantages compared to solid-phase methods.
22. Borona GM, Baldan A, Schiavon O, Ferruti P, Veronese FM: Poly(N-acryloylmorpholine) as a new soluble support for the liquid-phase synthesis of oligonucleotides. Tetrahedron Lett 1996, 37:4761-4764.
23. Hodosi G, Krepinsky JJ: Polymer-supported solution synthesis of oligosaccharides: probing glycosylations of MPEG-DOX-OH with 2-acetamidoglycopyranosyl derivatives. Synlett 1996:159-162.
24. Whitfield DM, Douglas SP, Krepinsky JJ: Metathesis of oligosaccharides. Relative stabilities of activated and deactivated glycosides of polyethylene glycol. Tetrahedron Lett 1992, 33:6795-6798.
25. Douglas SP, Whitfield DM, Krepinsky JJ: Polymer-supported solution synthesis of oligosaccharides using a novel versatile linker for the synthesis of D-mannopentaose, a structural unit of D-mannans of pathogenic yeasts. J Am Chem Soc 1995, 117:2116-2117. This report demonstrates the versatility of the DOX linker in oligosaccharide synthesis and provides a method (in supplementary material) that may be applied to the synthesis of other carbohydrates.
26. Wang Z-G, Douglas SP, Krepinsky JJ: Polymer-supported syntheses of oligosaccharides: using dibutylboron triflate to promote glycosylations with glycosyl trichloroacetimidates. Tetrahedron Lett 1996, 37:6985-6988.
27. Yamada K, Nishimura S-I: An efficient synthesis of sialoglycoconjugates on a peptidase-sensitive polymer support Tetrahedron Lett 1995, 36:9493-9496.
28. Tuchinsky A, Zehavi U: Improved, water-soluble, acceptor polymers for enzymatic glycosylation. React Polym 1996, 31:11-16.
29. Zhu J, Hegedus LS: Incorporation of chromium aminocarbene complex-derived amino acids into soluble poly(ethylene glycol) (PEG)-supported peptides. J Org Chem 1995, 60:5831-5837.
30. Stein PD, Hunt JT, Floyd DM, Moreland S, Dickinson KEJ, Mitchel C, Liu ECK, Webb ML, Murugesan N, Dickey J et al.: The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenes ulfonamide. J Med Chem 1994, 37:329-331.
31. Yoshino H, Ueda N, Nijima J, Sugumi H, Kotake Y, Koyanagi N, Yoshimatsu K, Asada M, Watanabe T, Nagasu T et al.: Novel sulfonamides as potential, systemically active antitumor agents. J Med Chem 1992, 35:2496-2497.
32. Ellingboe JW, Spinelli W, Winkley MW, Nguyen TT, Parsons RW, Moubarak IF, Kitzen JM, Von Engen D, Bagli JF: Class III antiarrhythmic activity of novel substituted 4-[(methylsulfonyl)amino]benzamides and sulfonamides. J Med Chem 1992, 35:705-716.
33. Park WKC, Auer M, Jaksche H, Wong C-H: Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev response element J Am Chem Soc 1996, 118:10150-10155. This report demonstrates the advantages of liquid-phase synthesis over solution and solid-phase methods by synthesizing and screening a small-molecule library for potential anti-HIV agents.
34. Zapp ML, Stern S, Green MR: Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. Cell 1993, 74:969-978.
35. Werstuck G, Zapp ML, Green MR: A non-canonical base pair within the human immunodeficiency virus Rev-responsive element is involved in both Rev and small molecule recognition. Chem Biol 1996, 3:129-137.
36. Bergbreiter DE, Caraway JW: Thermoresponsive polymer-bound substrates. J Am Chem Soc 1996, 118:6092-6093.
37. Bergbreiter DE, Kimmel T, Caraway JW: Modification of substrate reactivity using soluble polymeric supports. Tetrahedron Lett 1995, 36:4757-4760.
38. Jung KW, Zhao X, Janda KD: A linker that allows efficient formation of aliphatic C-H bonds on polymeric supports. Tetrahedron Lett 1996, 37:6491-6494.
39. Jung KW, Zhou X, Janda KD: Development of new linkers for the formation of aliphatic C-H bonds on polymeric supports. Tetrahedron 1997, in press.
40. Zhao X, Jung KW, Janda KD: Soluble polymer synthesis: an improved traceless linker methodology for aliphatic C-H bond formation. Tetrahedron Lett 1997, 38:977-980.
41. Kimura M, Nishigaki T, Koyama T, Hanabusa K, Shirai H: Functional metallomacrocycles and their polymers, part 34. Catalytic oxygenation of cyclohexene by water-soluble polymer containing manganese phthalocyanine complex. Reactive and Functional Polymers 1996, 29:85-90.
42. Kimura M, Nishigaki T, Koyama T, Hanabusa K, Shirai H: Functional metallomacrocycles and their polymers, 27. Catalase-like activity of water-soluble polymer containing a phthalocyanine-manganese complex. Macromol Chem Phys 1994, 195:3499-3508.
43. Yu Z, Liao S, Xu Y: Facile hydrodebromination of organic bromides with dihydrogen and polymer-anchored palladium catalyst under mild conditions. React Polym 1996, 29:151-157.
44. Han H, Janda KD: Soluble polymer-bound ligand-accelerated catalysis: asymmetric dihydroxylation. J Am Chem Soc 1996, 118:7632-7633.
45. Wentworth P Jr, Vandersteen AM, Janda KD: Poly(ethylene glycol) (PEG) as a reagent support: The preparation and utility of a PEG-triarylphosphine conjugate in liquid-phase organic synthesis (LPOS). J Chem Soc Chem Commun 1997, in press.
46. Wipf P, Venkatraman S: An improved protocol for azole synthesis with PEG supported Burgess reagent Tetrahedron Lett 1996, 37:4659-4662.