A direct method for the formation of peptide and carbohydrate dendrimers

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 19, 1999, Pages 2785-2788

  Mitchell, Jeffrey P ^a   Roberts, Kade D ^a   Langley, Jane ^b   Koentgen, Frank ^b   Lambert, John N ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; CARBONYL DERIVATIVE; DENDRIMER; HYDROXYLAMINE; KETONE; LEVULINIC ACID; PEPTIDE; POLYAMIDE;

ARTICLE; CHEMICAL MODIFICATION; GEL ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOASSAY; MOLECULAR RECOGNITION; PEPTIDE SYNTHESIS; POLYMERIZATION;

CARBOHYDRATES; CHROMATOGRAPHY, GEL; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GLYCOCONJUGATES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDES; POLYAMINES; POLYMERS;

EID: 0033523622     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00480-1     Document Type: Article

References (18)

1. 1. Tam, J. P. Proc. Natl. Acad. Sci. U S A. 1988, 85, 5409.
2. 2. Zanini, D.; Roy, R. J. Org. Chem. 1998, 63, 3486.
3. 3. Roy, R.; Zanini, D.; Meunier, S. J.; Romanowska, A. Chem. Commun. 1993, 1869.
4. 4. Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Eur. J. 1996, 2, 1115.
5. 5. Collins, M. L.; Irvine, B.; Tyner, D.; Fine, E.; Zayati, C.; Chang, C.; Horn, T.; Ahle, D.; Detmer, J.; Shen, L.-P.; Kolberg, J.; Bushnell, S.; Urdea, M. S.; Ho, D. D. Nuc. Acids Res. 1997, 25, 2979.
6. 6. Wang, J.; Jiang, M.; Nilsen, T. W.; Getts, R. C. J. Am. Chem. Soc. 1998, 120, 8281.
7. 7. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321.
8. 8. Zanini, D.; Roy, R. J. Org. Chem. 1996, 61, 7348.
9. 9. Zanini, D.; Roy, R. J. Am. Chem. Soc. 1997, 119, 2088.
10. 10. Palcic, M. M.; Li, H.; Zanini, D.; Bhella, R. S.; Roy, R. Carbohydr Res. 1997, 305, 433.
11. 11. Galili, U.; LaTemple, D. C. Immunol. Today. 1997, 18, 281.
12. 12. LaTemple, D. C.; Henion, T. R.; Anaraki, F.; Galili, U. Cancer Res. 1996, 56, 3069.
13. 13. Aoi, K.; Itoh, K.; Okada, M. Macromolecules. 1995, 28, 5391.
14. 14. Page, D.; Zanini, D.; Roy, R. Bioorg. Med. Chem. 1996, 4, 1949.
15. 15. Canne, L. E.; Ferre-D'Amare, A. R.; Burley, S. K.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 2998.
16. 16. Cervigni, S. E.; Dumy, P.; Mutter, M. Angew. Chem. Intl. Edn. Engl. 1996, 35, 1230.
17. 17. Singh, P. Bioconjugate Chem. 1998, 9, 54.
18. 18. In a control experiment, reaction of unmodified G1 PAMAM (1) with lactose also delivered a conjugate, presumably formed by condensation of the dendrimer primary amines with lactose carbonyl groups. However, the formation of this material could be reversed by titration with ethylenediamine. In the case of oxime conjugate 7, no evidence of reversion to lactose and 5 was observed even upon addition of a 100-fold excess of ethylenediamine