Synthesis and manipulation of orthogonally protected dendrimers: Building blocks for library synthesis

Angewandte Chemie - International Edition

Volumn 43, Issue 39, 2004, Pages 5178-5180

  Steffensen, Mackay B ^a   Simanek, Eric E ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Amines; Dendrimers; Protecting groups; Synthesis design

Indexed keywords

DRUG DOSAGE; FORESTRY; FRUITS; FUNCTIONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BUILDING BLOCKS; DEPROTECTION STRATEGY; DRUG-DELIVERY SYSTEMS;

DENDRIMERS;

DENDRIMER;

ARTICLE; DEPROTECTION REACTION; SYNTHESIS;

ACYLATION; AMINO ACIDS; CHROMATOGRAPHY, THIN LAYER; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DELIVERY SYSTEMS; INDICATORS AND REAGENTS; TRIAZINES;

DRUGS; FRUITS; FUNCTIONAL GROUPS; REACTION KINETICS; SYNTHESIS; TREES;

EID: 6044260213     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460031     Document Type: Article

References (37)

1. a) S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819-3867;
2. b) G. R. Newkome, F. Vögtle, C. N. Moorefield, Dendrimers and Dendrons: Concepts, Syntheses, Applications, VCH, New York, 2001;
3. c) J. M. J. Frèchet, D. A. Tomalia, Dendrimers and Other Dendritic Polymers, Wiley, New York, 2002.
4. a) M. Okaniwa, K. Takeuchi, M. Asai, M. Ueda, Macromolecules 2002, 35, 6232-6238;
5. b) S. P. Rannard, N. J. Davis, J. Am. Chem. Soc. 2000, 122, 11 729-11 770.
6. a) P. Singh, Bioconjugate Chem. 1998, 9, 54-63;
7. b) G. R. Newkome, C. D. Weis, C. N. Moorefield, G. R. Baker, B. J. Childs, J. Epperson, Angew. Chem. 1998, 110, 318-321; Angew. Chem. Int. Ed. 1598, 37, 307-310;
8. b) G. R. Newkome, C. D. Weis, C. N. Moorefield, G. R. Baker, B. J. Childs, J. Epperson, Angew. Chem. 1998, 110, 318-321; Angew. Chem. Int. Ed. 1598, 37, 307-310;
9. c) G. R. Newkome, B. J. Childs, M. J. Rourk, G. R. Baker, C. N. Moorefield, Biotechnol. Bioeng. 1999, 61, 243-253;
10. d) J. R. Baker, A. Quintana, L. Piehler, M. Banazak-Holl, D. Tomalia, E. Raczka, Biomed. Microdevices 2001, 3, 61-69.
11. a) W. Zhang, D. T. Nowlan III, L. M. Thomson, W. M. Lackowski, E. E. Simanek, J. Am. Chem. Soc. 2001, 123, 8914-8922;
12. b) Z. Bo, A. Schäfer, P. Franke, A. D. Schlüter, Org. Lett. 2000, 2, 1645-1648;
13. c) H.-F. Chow, C.-F. Leung, K.-W. Wong, L. Xi, Angew. Chem. 2003, 115, 5069-5073; Angew. Chem. Int. Ed. 2003, 42, 4919-4923;
14. c) H.-F. Chow, C.-F. Leung, K.-W. Wong, L. Xi, Angew. Chem. 2003, 115, 5069-5073; Angew. Chem. Int. Ed. 2003, 42, 4919-4923;
15. d) S. Li, M. L. Szalai, R. M. Kevwitch, D. V. McGrath, J. Am. Chem. Soc. 2003, 125, 10516-10517;
16. e) K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1991, 1059-1076;
17. f) W. Zhang, S. E. Tichy, L. M. Pérez, G. Maria, P. A. Lindahl, E. E. Simanek, J. Am. Chem. Soc. 2003, 125, 5086-5094.
18. a) S.-E. Stiriba, H. Frey, R. Haag, Angew. Chem. 2002, 114, 1385-1390; Angew. Chem. Int. Ed. 2002, 41, 1329-1334;
19. a) S.-E. Stiriba, H. Frey, R. Haag, Angew. Chem. 2002, 114, 1385-1390; Angew. Chem. Int. Ed. 2002, 41, 1329-1334;
20. b) F. Aulenta, W. Hayes, S. Rannard, Eur. Polym. J. 2003, 39, 1741-1771;
21. c) M. J. Cloninger, Curr. Opin. Chem. Biol. 2002, 6, 742-748;
22. d) R. Esfand, D. A. Tomalia, Drug Discovery Today 2001, 6, 427-436;
23. e) A. K. Patri, I. J. Majoros, J. R. Baker, Jr., Curr. Opin. Chem. Biol. 2002, 6, 466-471.
24. Materials are available in limited supply to other investigators by contacting Professor Simanek.
25. Inspiration from: C.-H. Wong, X.-S. Ye, Z. Zhang, J. Am. Chem. Soc. 1998, 120, 7137-7138.
26. a) J. H. van Boom, P. M. J. Burgers, Tetrahedron Lett. 1976, 17, 4875-4878;
27. b) N. Jeker, C. Tamm, Helv. Chim. Acta 1984, 67, 190.
28. S. Hanessian, P. Lavallee, Can. J. Chem. 1977, 55, 562-565.
29. J. Connor, A. J. Schroit, Biochemistry 1988, 27, 848-851.
30. D. A. Westerberg, P. L. Carney, P. E. Rogers, S. J. Kline, D. K. Johnson, J. Med. Chem. 1989, 32, 236-243.
31. M. B. Steffensen, E. E. Simanek, Org. Lett. 2003, 5, 2359-2361.
32. a) S. Sinha, P. Ilankumaran, S. Chandrasekaran, Tetrahedron Lett. 1999, 40, 771-774;
33. b) R. G. Bhat, S. Sinha, S. Chandrase-karan, Chem. Commun. 2002, 812-813;
34. c) P. R. Sridhar, S. Chandrasekaran, Org. Lett. 2002, 4, 4731-4733.
35. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
36. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
37. Fruit-salad trees are commercially available: http://www.fruitsaladtrees. com/.