Facile synthesis of second-generation dendrons with an orthogonal functional group at the focal point

Synthetic Communications

Volumn 39, Issue 11, 2009, Pages 1966-1980

  Cheedarala, Ravi Kumar ^a   Sunkara, Vijaya ^a   Park, Joon Won ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Dendrons; Deprotection; Divergent; Epoxy

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; DENDRIMER;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67650045444     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802627076     Document Type: Article

References (49)

1. Wu, P.; Michael, M.; Hunt, J. N.; Robert, V.; Eiton, K.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Multivalent bifunctional dendrimers prepared by click chemistry. Chem. Commun. 2005, 46, 5775-5777.
2. Gillies, E. R.; Frechet, J. M. J. Designing macromolecules for therapeutic applications: Polyester dendrimer-poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture. J. Am. Chem. Soc. 2002, 124, 47, 14137-14146.
3. Buhleier, E.; Wehner, W.; Voegtle, F. ''Cascade-'' and "nonskid-chain-like" syntheses of molecular cavity topologies. ynthesis 1978, 2, 155-158.
4. Hawker, C. J.; Frechet, J. M. J. Preparation of polymers with controlled molecular architecture: A new convergent approach to dendritic macro- molecules. J. Am. Chem. Soc. 1990, 112(21), 7638-7647.
5. (a) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. A new class of polymers: Starburst-dendritic macromolecules. Polym. J. 1985, 17 (1), 117-132.
6. (b) Morosini, V.; Frochot, C.; Barberi-Heyob, M.; Schneider, R. Divergent synthesis of novel unsymme- trical dendrons containing photosensitizing units. Tetrahedron Lett. 2006, 47(49), 8745-8749.
7. Hawker, C.; Frechet, J. M. J. A new convergent approach to monodisperse dendritic macromolecules. Chem. Commun. 1990, 15, 1010-1013.
8. (a) Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendritic Macromole- cules: Concept, Synthesis, and Perspectives; VCH Publishing: Weinheim, Germany, 1996;
9. (b) Newkome, G. R.; Moorefield, C. N. In Comprehensive Supramolecular Chemistry; D. N. Reinhoudt, (Ed.); Elsevier Science: New York, 1996, vol. 10;
10. (c) Tomalia, D. A.; Naylor, A. M.; Goddard III, W. A. Starburst dendrimers: Molecular-level control of size, shape, surface
11. chemistry, topology, and flexibility in the conversion of atoms to macroscopic materials. Angew. Chem. Int. Ed. 1990, 29(2), 138-175.
12. (a) Wooley, K. L.; Hawker, C. J.; Frechet, J. M. J. Hyperbranched macromo- lecules via a novel double-stage convergent growth approach. J. Am. Chem. Soc. 1991, 113(11), 4252-4261;
13. (b) Ihre, H.; Hult, A.; Frechet, J. M. J.; Gitsov, I. Double-stage convergent approach for the synthesis of functiona- lized dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid. Macromolecules 1998, 31(13), 4061-4068.
14. Kawaguchi, T.; Walker, K. L.; Wilkins, C. L.; Moore, J. S. Double exponential dendrimer growth. J. Am. Chem. Soc. 1995, 117(8), 2159-2165.
15. Wolley, K. L.; Hawker, C. J.; Frechet, J. M. J. Branched monomers as the source for quick access to dendrimers. Angew. Chem. Int. Ed. 1994, 33(1),82-85.
16. Freeman, A. W.; Frechet, J. M. J. A rapid, orthogonal synthesis of poly (benzyl ester) dendrimers via an "activated" monomer approach. Org. Lett.1999, 1(4), 685-687.
17. (a) Jansen, J. F. G. A.; de Brabander van den Berg, E. M. M.; Meijer, E. W. Encapsulation of guest molecules into a dendritic box. Science 1994, 266(5188), 1226-1229;
18. (b) Hawker, C. J.; Frechet, J. M. J. Monodispersed dendritic polyesters with removable chain ends: a versatile approach to globular macromolecules with chemically reversible polarities. J. Chem. Soc., Perkin Trans. 1 1992, 19, 2459-2469;
19. (c) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, Piet W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Homogeneous catalysts based on silane dendri- mers functionalized with arylnickel(II) complexes. Nature 1994, 372, 659-663.
20. (a) Svenson, S.; Tomalia, D. A. Dendrimers in biomedical applications- Reflections on the field. Adv. Drug Deliver. Rev. 2005, 57(15), 2106-2129;
21. (b) Najlah, M.; D'Emanuele, A. Crossing cellular barriers using dendrimer nanotechnologies. Curr. Opin. Pharmacol. 2006, 6(5), 522-527.
22. (a) Haensler, J.; Szoka, Jr., F. C. Polyamidoamine cascade polymers mediate efficient transfection of cells in culture. Bioconjugate Chem. 1993, 4(5), 372379;
23. (b) Tang, M. X.; Redemann, C. T.; Szoka Jr., F. C. In vitro gene delivery by degraded polyamidoamine dendrimers. Bioconjugate Chem. 1996, 7(6), 703-714.
24. Lee, C. C.; MacKay, J. A.; Frechet, J. M. J.; Szoka, F. C. Designing dendri- mers for biological applications. Nat. Biotechnol. 2005, 23(12), 1517-1526.
25. Milhem, O. M.; Myles, C.; McKeown, N. B.; Attwood, D.; D'Emanuele, A. Polyamidoamine starburst dendrimers as solubility enhancers. Int. J. Pharm.2000, 197(1), 239-241.
26. Hong, B. J.; Oh, S. J.; Youn, T. O.; Kwon, S. H.; Park, J. W. Nanoscale- controlled spacing provides DNA microarrays with the SNP discrimination efficiency in solution phase. Langmuir 2005, 21(10), 4257-4261.
27. Le Berre, V.; Trevisiol, E.; Dagkessamanskaia, A.; Sokol, S.; Caminade, A. M.; Majoral, J. P.; Meunier, B.; Francois, J. Dendrimeric coating of glass slides for sensitive DNA microarrays analysis. Nucl. Acids Res. 2003, 31(16), e88/1-e88/8.
28. (a) Li, N. B.; Kwak, J. A penicillamine biosensor based on tyrosinase immobilized on nano-Au/PAMAM dendrimer modified gold electrode. Electroa- nal. 2007, 19(23), 2428-2436;
29. (b) Hierlemann, A.; Campbell, J. K.; Baker, L. A.; Crooks, R. M.; Ricco, A. J. Structural distortion ofdendrimers on gold surfaces: A tapping-mode AFM investigation. J. Am. Chem. Soc. 1998, 120(21), 5323-5324.
30. Rozkiewicz, D. I.; Brugman, W.; Kerkhoven, R. M.; Ravoo, B. J.; Reinhoudt, D. N. Dendrimer-mediated transfer printing of DNA and RNA microarrays. J. Am. Chem. Soc. 2007, 129(37), 11593-11599.
31. Woo, S. W.; Lee, Y.; Sunkara, V.; Cheedarala, R. K.; Shin, H. S.; Choi, H. C.; Park, J. W. ''Fingertip''-guided noncovalent functionalization of carbon nanotubes by dendrons. Langmuir 2007, 23(23), 11373-11376.
32. Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M. L. Metal supported on dendronized magnetic nanoparticles: Highly selective hydroformylation catalysts. J. Am. Chem. Soc. 2006, 128(15), 5279-5282.
33. (a) Cardona, C. M.; Gawley, R. E. An improved synthesis of a trifurcated newkome-type monomer and orthogonally protected two-generation den- drons. J. Org. Chem. 2002, 67(4), 1411-1413;
34. (b) Nierengarten, J. F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J. P.; Boudon, C.; Gross, M. Macrocyclization on the fullerene core: Direct regio- and diastereoselective multi-functionalization of [60]fuller- ene, and synthesis of fullerene-dendrimer derivatives. Helv. Chim. Acta 1997, 80(7), 2238-2276;
35. (c) Habicher, T.; Diederich, F.; Gramlich, V. Catalytic den- drophanes as enzyme mimics: Synthesis, binding properties, micropolarity effect, and catalytic activity of dendritic thiazolio-cyclophanes. Helv. Chim. Acta 1999, 82(7), 1066-1095;
36. (d) Koenig, S.; Muller, L.; Smith, D. K. Dendritic biomimicry: Microenvironmental hydrogen-bonding effects on tryptophan fluorescence. Chemistry (Ger.) 2001, 7(5), 979-986;
37. (e) Smith, D. K.; Muller, L. Dendritic biomimicry: Microenvironmental effects on tryptophan fluorescence. Chem. Commun. 1999, 18, 1915-1916.
38. (a) Hong, B. J.; Shim, J. Y.; Oh, S. J.; Park, J. W. Self-assembly of a dendron through multiple ionic interaction to give mesospacing between reactive amine groups on the surface. Langmuir 2003, 19(6), 2357-2365;
39. (b) Hong, B. J.; Sunkara, V.; Park, J. W. DNA microarrays on nanoscale-controlled surface. Nucleic Acids Res. 2005, 33(12), e106/1-e106/8;
40. (c) Sunkara, V.; Hong, B. J.; Park, J. W. Sensitivity enhancement of DNA microarray on nano-scale controlled surface by using a streptavidin-fluorophore conjugate. Biosens. Bioelectron. 2007, 22(7), 1532-1537;
41. (d) Choi, Y. S.; Yoon, C. W.; Lee, H. D.; Park, M.; Park, J. W. Efficient protein-ligand interaction by guaranteeing mesospacing between immobilized biotins. Chem. Commun. 2004, 11, 1316-1317;
42. (e) Jung, Y. J.; Hong, B. J.; Zhang, W.; Tendler, S. J. B.; Williams, P. M.; Allen, S.; Park, J. W. Dendron arrays for the force-baseddetection of DNA hybridization events. J. Am. Chem. Soc. 2007, 129(30), 9349-9355.
43. (a) Pirrung, M. C. How to make a DNA chip. Angew. Chem. Int. Ed. 2002, 41(8), 1276-1289;
44. (b) Cheung, V. G.; Morley, M.; Aguilar, F.; Massimi, A.; Kucherlapati, R.; Childs, G. Making and reading microarrays. Nat. Genet. 1999, 21, 15-19;
45. (c) Zammatteo, N.; Jeanmart, L.; Hamels, S.; Courtois, S.; Louette, P.; Hevesi, L.; Remacle, J. Comparison between different strategies of covalent attachment of DNA to glass surfaces to build DNA microarrays. Anal. Biochem. 2000, 280(1), 143-150.
46. Newkome, G. R.; Lin, X. Symmetrical, four-directional, poly(ether-amide) cascade polymers. Macromolecules 1991, 24(6), 1443-1444.
47. Shashoua, V. E.; Jacob, J. N.; Ridge, R.; Campbell, A.; Baldessarini, R. J. y-Aminobutyric acid esters, I: Synthesis, brain uptake, and pharmacological studies of aliphatic and steroid esters of y-aminobutyric acid. J. Med. Chem.1984, 27(5), 659-664.
48. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Low temperature asymmetric epoxidation of unfunctionalized olefins catalyzed by (salen)Mn(III) complexes. Tetrahedron Lett. 1995, 36(31), 5457-5460.
49. Ohno, T.; Ogawa, K.; Yano, S.; Fukushima, M.; Suzuki, N.; Asao, T. Synthesis and structure-activity relationship of 4-substituted benzoic acids and their inhibitory effect on the biosynthesis of fatty acids and sterols. Arch.Pharm. 2005, 338(4), 147-158.