Peptide dendrimers from natural amino acids

Chemistry - A European Journal

Volumn 5, Issue 7, 1999, Pages 2133-2138

  Kim, Yoonkyung ^a   Zeng, Fanwen ^a   Zimmerman, Steven C ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Amino acids; Dendrimers; Peptides; Solid phase synthesis

Indexed keywords

AMINO ACID; DICYCLOHEXYLAMINE DERIVATIVE; PEPTIDE; POLYLYSINE;

AMINO ACID SEQUENCE; ARTICLE; CATALYST; CHIRALITY; GEL PERMEATION CHROMATOGRAPHY; HYDROGENATION; MASS SPECTROMETRY; PROTEIN ANALYSIS; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033031449     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990702)5:7<2133::AID-CHEM2133>3.0.CO;2-J     Document Type: Article

References (25)

1. a) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules. Concepts, Syntheses, Perspectives, VCH, Cambridge, 1996;
2. b) F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712.
3. L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600 and references therein.
4. R. G. Denkewalter, J. F. Kolc, W. J. Lukasavage U.S. Pat. 4410688, [Chem. Abstr. 1984, 100, 103907 p].
5. a) L. J. Twyman, A. E. Beezer, J. C. Mitchell, Tetrahedron Lett. 1994, 35, 4423-4424;
6. b) D. Zanini, R. Roy, J. Org. Chem. 1996, 61, 7348-7354;
7. c) D. Ranganathan, S. Kurur, Tetrahedron Lett. 1997, 38, 1265-1268;
8. d) S. J. E. Mulders, A. J. Brouwer, R. M. J. Liskamp, Tetrahedron Lett. 1997, 38, 3085-3088.
9. a) H. W. I. Peerlings, E. W. Meijer, Chem. Eur. J. 1997, 3, 1563-1570;
10. b) J. R. McElhanon, D. V. McGrath, J. Am. Chem. Soc. 1998, 120, 1647-1656;
11. c) P. Murer, D. Seebach, Helv. Chim. Acta 1998, 81, 603-630.
12. L. L. McKinney, E. H. Uhing, E. A. Setzkorn, J. C. Cowan, J. Am. Chem. Soc. 1951, 73, 1641-1644.
13. E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1993, 105, 1370-1372; Angew. Chem. Int. Ed. Engl. 1993, 52, 1308-1311.
14. E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1993, 105, 1370-1372; Angew. Chem. Int. Ed. Engl. 1993, 52, 1308-1311.
15. H. Han, M. M. Wolfe, S. Brenner, K. D. Janda, Proc. Natl. Acad. Sci. USA 1995, 92, 6419-6423.
16. a) T. M. Chapman, G. L. Hillyer, E. J. Mahan, K. A. Shaffer, J. Am. Chem. Soc. 1994, 116, 11195-11196;
17. b) T. M. Chapman, E. J. Mahan, Polym. Mater. Sci. Eng. 1997, 77, 103-104.
18. 2. A Whelk-O chiral HPLC column was used for the analysis and co-injection of L and D isomers of each amino acid gave baseline separation. W. H. Pirkle, C. J. Welch, J. Chromatogr. 1994, 683, 347-353.
19. Other amino acids have been successfully prepared using this method. The yields for the cyanoethylation and hydrogenation are the following: cyanoethylation of glycine (94%), L-alanine (91%), L-phenylalanine (74%), L-serine (98%); hydrogenation of glycine (100%), L-alanine (100%), L-phenylalanine (97%), L-serine (81%). The hydrogenation products were contaminated with a trace amount of cobalt.
20. n 5000.
21. 1H NMR) for each generation.
22. M. Schnölzer, P. Alewood, A. Jones, D. Alewood, S. B. H. Kent, Int. J. Pept. Protein Res. 1992, 40, 180-193.
23. For the fourth-generation leucine-based dendrimer with PEG, the molecular weight ratio of the dendrimer portion and the PEG was approximately 1:1.
24. J. M. J. Fréchet, I. Gitsov, Macromol. Symp. 1995, 98, 441-465.
25. S. Zalipsky, C. Gilon, A. Zilkha, J. Macromol. Sci. Chem. 1984, A21, 839-845.