Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 11
452
Views
15
CrossRef citations to date
0
Altmetric
Original Articles

Facile Synthesis of Second-Generation Dendrons with an Orthogonal Functional Group at the Focal Point

, &
Pages 1966-1980 | Received 18 Sep 2008, Published online: 27 Apr 2009

REFERENCES

  • 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 .
  • 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 .
  • Buhleier , E. ; Wehner , W. ; Voegtle , F. “Cascade-” and “nonskid-chain-like” syntheses of molecular cavity topologies . Synthesis 1978 , 2 , 155 – 158 .
  • Hawker , C. J. ; Frechet , J. M. J. Preparation of polymers with controlled molecular architecture: A new convergent approach to dendritic macromolecules . J. Am. Chem. Soc. 1990 , 112 ( 21 ), 7638 – 7647 .
  • (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 . (b) Morosini , V. ; Frochot , C. ; Barberi-Heyob , M. ; Schneider , R. Divergent synthesis of novel unsymmetrical dendrons containing photosensitizing units . Tetrahedron Lett. 2006 , 47 ( 49 ), 8745 – 8749 .
  • Hawker , C. ; Frechet , J. M. J. A new convergent approach to monodisperse dendritic macromolecules . Chem. Commun. 1990 , 15 , 1010 – 1013 .
  • (a) Newkome , G. R. ; Moorefield , C. N. ; Vogtle , F. Dendritic Macromolecules: Concept, Synthesis, and Perspectives ; VCH Publishing : Weinheim , Germany , 1996 ; (b) Newkome , G. R. ; Moorefield , C. N. In Comprehensive Supramolecular Chemistry ; D. N. Reinhoudt , (Ed.); Elsevier Science : New York , 1996 , vol. 10 ; (c) Tomalia, D. A.; Naylor, A. M.; Goddard III, W. A. Starburst dendrimers: Molecular-level control of size, shape, surface chemistry, topology, and flexibility in the conversion of atoms to macroscopic materials. Angew. Chem. Int. Ed. 1990, 29(2), 138–175 .
  • (a) Wooley , K. L. ; Hawker , C. J. ; Frechet , J. M. J. Hyperbranched macromolecules via a novel double-stage convergent growth approach . J. Am. Chem. Soc. 1991 , 113 ( 11 ), 4252 – 4261 ; (b) Ihre , H. ; Hult , A. ; Frechet , J. M. J. ; Gitsov , I. Double-stage convergent approach for the synthesis of functionalized dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid . Macromolecules 1998 , 31 ( 13 ), 4061 – 4068 .
  • Kawaguchi , T. ; Walker , K. L. ; Wilkins , C. L. ; Moore , J. S. Double exponential dendrimer growth . J. Am. Chem. Soc. 1995 , 117 ( 8 ), 2159 – 2165 .
  • 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 .
  • 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 .
  • (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 ; (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 ; (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 dendrimers functionalized with arylnickel(II) complexes . Nature 1994 , 372 , 659 – 663 .
  • (a) Svenson , S. ; Tomalia , D. A. Dendrimers in biomedical applications–Reflections on the field . Adv. Drug Deliver. Rev. 2005 , 57 ( 15 ), 2106 – 2129 ; (b) Najlah , M. ; D' Emanuele , A. Crossing cellular barriers using dendrimer nanotechnologies . Curr. Opin. Pharmacol. 2006 , 6 ( 5 ), 522 – 527 .
  • (a) Haensler , J. ; Szoka , Jr. , F. C. Polyamidoamine cascade polymers mediate efficient transfection of cells in culture . Bioconjugate Chem. 1993 , 4 ( 5 ), 372 – 379 ; (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 .
  • Lee , C. C. ; MacKay , J. A. ; Frechet , J. M. J. ; Szoka , F. C. Designing dendrimers for biological applications . Nat. Biotechnol. 2005 , 23 ( 12 ), 1517 – 1526 .
  • 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 .
  • 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 .
  • 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 .
  • (a) Li , N. B. ; Kwak , J. A penicillamine biosensor based on tyrosinase immobilized on nano-Au/PAMAM dendrimer modified gold electrode. Electroanal. 2007, 19(23), 2428–2436; (b) Hierlemann , A. ; Campbell , J. K. ; Baker , L. A. ; Crooks , R. M. ; Ricco , A. J. Structural distortion of dendrimers on gold surfaces: A tapping-mode AFM investigation. J. Am. Chem. Soc. 1998, 120(21), 5323–5324.
  • 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 .
  • 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 .
  • 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 .
  • (a) Cardona , C. M. ; Gawley , R. E. An improved synthesis of a trifurcated newkome-type monomer and orthogonally protected two-generation dendrons . J. Org. Chem. 2002 , 67 ( 4 ), 1411 – 1413 ; (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]fullerene, and synthesis of fullerene-dendrimer derivatives . Helv. Chim. Acta 1997 , 80 ( 7 ), 2238 – 2276 ; (c) Habicher , T. ; Diederich , F. ; Gramlich , V. Catalytic dendrophanes as enzyme mimics: Synthesis, binding properties, micropolarity effect, and catalytic activity of dendritic thiazolio-cyclophanes . Helv. Chim. Acta 1999 , 82 ( 7 ), 1066 – 1095 ; (d) Koenig , S. ; Muller , L. ; Smith , D. K. Dendritic biomimicry: Microenvironmental hydrogen-bonding effects on tryptophan fluorescence . Chemistry (Ger.) 2001 , 7 ( 5 ), 979 – 986 ; (e) Smith , D. K. ; Muller , L. Dendritic biomimicry: Microenvironmental effects on tryptophan fluorescence . Chem. Commun. 1999 , 18 , 1915 – 1916 .
  • (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 ; (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 ; (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 ; (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 ; (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-based detection of DNA hybridization events . J. Am. Chem. Soc. 2007 , 129 ( 30 ), 9349 – 9355 .
  • (a) Pirrung , M. C. How to make a DNA chip . Angew. Chem. Int. Ed. 2002 , 41 ( 8 ), 1276–1289; (b) Cheung , V. G. ; Morley , M. ; Aguilar , F. ; Massimi , A. ; Kucherlapati , R. ; Childs , G. Making and reading microarrays . Nat. Genet. 1999 , 21 , 15 – 19 ; (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 .
  • Newkome , G. R. ; Lin , X. Symmetrical, four-directional, poly(ether-amide) cascade polymers. Macromolecules 1991, 24(6), 1443–1444.
  • Shashoua , V. E. ; Jacob , J. N. ; Ridge , R. ; Campbell , A. ; Baldessarini , R. J. γ-Aminobutyric acid esters, I: Synthesis, brain uptake, and pharmacological studies of aliphatic and steroid esters of γ-aminobutyric acid . J. Med. Chem. 1984 , 27 ( 5 ), 659 – 664 .
  • 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 .
  • 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 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.