Chemo-enzymatic synthesis of a trisaccharide-linked peptide aimed at improved drug-delivery

Current Drug Delivery

Volumn 2, Issue 3, 2005, Pages 215-222

  Johnstone, Ken D ^a   Dieckelmann, Manuela ^b   Jennings, Michael P ^a   Toth, Istvan ^a   Blanchfield, Joanne T ^a,b  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Chemo enzymatic; Drug targeting; Endomorphin; Glycopeptide; Glycosyltransferase; Oligosaccharide; Peptide drug delivery; Solid phase synthesis

Indexed keywords

ENDOMORPHIN 1; GLYCOSYLTRANSFERASE; PROTEIN LGTA; UNCLASSIFIED DRUG;

ARTICLE; DRUG DELIVERY SYSTEM; DRUG TARGETING; ENZYME ISOLATION; NEISSERIA MENINGITIDIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID;

BACTERIAL PROTEINS; BASE SEQUENCE; CARBOHYDRATE SEQUENCE; DNA PRIMERS; DNA, RECOMBINANT; DRUG DELIVERY SYSTEMS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; N-ACETYLGLUCOSAMINYLTRANSFERASES; PEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRISACCHARIDES;

EID: 21744433665     PISSN: 15672018     EISSN: None     Source Type: Journal    
DOI: 10.2174/1567201054367977     Document Type: Article

References (36)

1. Belot, F.; Rabuka, D.; Fukuda, M.; Hindsgaul, O. Tetrahedron Lett., 2002, 43, 7743-7747.
2. Blixt, O.; Allin, K.; Pereira, L.; Datta, A.; Paulson, J. J. Am. Chem. Soc., 2002, 124, 5739-5746.
3. Crout, D.; Vic, G. Curr. Opin. Chem. Biol. 1998, 2, 98-111.
4. Johnson, K. Glycoconj. J., 1999, 16, 141-146.
5. Koeller, K.; Wong, C.-H. Chemical Reviews. 2000, 100, 4465-4493.
6. Ohrlein, R. Top. Curr. Chem., 1999, 200, 227-254.
7. Sengupta, P.; Misra, A.; Suzuki, M.; Fukuda, M.; Hindsgaul, O. Tetrahedron Lett., 2003, 44, 6037-6042.
8. Suzuki, K.; Matsuo, I.; Isomura, M.; Ajisaka, K. J. Carbohydr. Chem., 2002, 21, 99-111.
9. Yan, F.; Mehta, S.; Eichler, E.; Wakarchuk, W.; Gilbert, M.; Schur, M.; Whitfield, D. J. Org. Chem., 2003, 65, 2426-2431.
10. Davis, B. J. Chem. Soc., Perkin Trans. 1, 2000, 2137-2160.
11. Paulsen, H. Angew. Chem., Int. Ed., 1982, 21, 155-224.
12. Schmidt, R. Angew. Chem., Int. Ed., 1986, 25, 212-235.
13. Parish, C.; Freeman, C.; Brown, K.; Francis, D.; Cowden, W. Cancer Res., 1999, 59, 3433-3441.
14. Lingwood, C. Curr. Opin. Chem. Biol., 1998, 2, 695-700.
15. Przewlocka, B.; Mika, J.; Labuz, D.; Toth, G.; Przewlocki, R. Eur. J. Pharmacol., 1999, 367, 189-196.
16. Zadina, J.; Hackler, L.; Ge, L.-J.; Kastin, A. Nature, 1997, 386, 499-502.
17. Blanchfield, J.T.; Dutton, J.L.; Hogg, R.C.; Craik, D.J.; Adams, D.J.; Lewis, R.J.; Alewood, P.P.; Toth, I. Lett. Pept. Sci., 2002, 8, 235-239.
18. Blanchfield, J.T.; Dutton, J.L.; Hogg, R.C.; Gallagher, O.P.; Craik, D.J.; Jones, A.; Adams, D.J.; Lewis, R.J.; Alewood, P.P.; Toth, I. J. Med. Chem., 2003, 46, 1266-1272.
19. Kellam, B.; Drouillat, B.; Dekany, G.; Starr, M.S.; Toth, I. Int. J. Pharm., 1998, 161, 55-64.
20. Wong, C.-H.; Schuster, M.; Wang, P.; Sears, P. J. Am. Chem. Soc., 1993, 115, 5893-5901.
21. Meldal, M.; St Hilaire, P. Curr. Opin. Chem. Biol., 1997, 1, 552-563.
22. Priem, B.; Gilbert, M.; Wakarchuk, W.; Heyraud, A.; Samain, E. Glycobiology, 2002, 12, 235-240.
23. Wakarchuk, W.; Martin, A.; Jennings, M.; Moxon, E.; Richards, J. J. Biol. Chem., 1996, 271, 19166-19173.
24. Tong, Y.; Arking, D.; Ye, S.; Reinhold, B.; Reinhold, V.; Stein, D. Glycobiology, 2002, 12, 523-533.
25. Plested, J.; Makepeace, K.; Jennings, M.; Gidney, M.; Lacelle, S.; Brisson, J.-R.; Cox, A.; Martin, A.; Bird, A.; Tang, C.; Mackinnon, P.; Richards, J.; Moxon, E. Infect. Immun., 1999, 67, 5417-5426.
26. Berrington, A.; Tan, Y.-C.; Srikhanta, Y.; Kuipers, B.; van der Ley, P.; Peak, I.; Jennings, M. FEMS Immunol. Med. Microbiol., 2002. 34, 267-275.
27. Power, P.; Jennings, M. FEMS Microbiol. Lett., 2003, 218, 211-222.
28. Blixt, O.; van Die, I.; Norberg, T.; van den Eijnden, D. Glycobiology, 1999, 9, 1061-1071.
29. Virji, M.; Makepeace, K.; Peak, I.R.; Ferguson, D.J.; Jennings, M.P.; Moxon, E.R. Mol. Microbiol., 1995, 18, 741-754.
30. Alexander, H. In Bacterial and Mycotic Infections of Man., R. Dabos and J. London, Ed.: Pitman Medical Publishing Co.: 1965, pp. 724-741.
31. Sambrook, J.; Fritsch, E.; Maniatis, T. Molecular Cloning: a Laboratory Manual, Cold Spring Harbour Laboratory: New York, 1989.
32. Toth, I.; Malkinson, J.; Flinn, N.; Drouillat, B.; Horvath, A.; Erchegyi, J.; Idei, M.; Venetianer, A.; Artursson, P.; Lazorova, L.; Szende, B.; Keri, G. J. Med. Chem., 1999, 42, 4010-4013.
33. Shiozaki, M.; Mochizuki, T.; Hanzawa, H.; Haruyama, H. Carbohydr. Res., 1996, 288, 99-108.
34. Murphy, P.; Bradley, H.; Tosin, M.; Pitt, N.; Fitzpatrick, G.; Glass, W. J. Org. Chem., 2003, 68, 5692-5704.
35. Suami, T.; Machinami, T.; Hisamatsu, T. J. Am. Chem. Soc., 1979, 22, 247-250.
36. Kaiser, E.; Colescott, R.; Bossinger, C.; Cook, P. Anal. Biochem., 1970, 34, 595-8.