Chemoselective immobilization of biomolecules through aqueous Diels-Alder and PEG chemistry

Tetrahedron Letters

Volumn 49, Issue 16, 2008, Pages 2510-2513

  Sun, Xue Long ^a   Yang, LiuChun ^b   Chaikof, Elliot L ^b  

^a CLEVELAND STATE UNIVERSITY   (United States)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Biomolecules; Chemical selective immobilization; Diels Alder reaction; Poly(ethylene glycol)

Indexed keywords

BIOTIN; CYCLOPENTADIENE DERIVATIVE; GLASS; LACTOSE; MACROGOL; MALEIMIDE; PROTEIN A;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CONFOCAL FLUORESCENCE IMAGING; CONJUGATE; DIELS ALDER REACTION; IMAGING; IMMOBILIZATION; LINEAR SYSTEM; MOLECULAR DYNAMICS; SOLID STATE; STRUCTURE ANALYSIS; SURFACE PROPERTY;

ALNUS;

EID: 40849114388     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.111     Document Type: Article

References (27)

1. Rideout D.C., and Breslow R. J. Am. Chem. Soc. 102 (1980) 7816-7817
2. Li C.J. Chem. Rev. 105 (2005) 3095-3165
3. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed. 44 (2005) 3275-3279
4. Jäger M., Polborn K., and Steglich W. Tetrahedron Lett. 36 (1995) 861-864
5. Pozsgay V., Vieira N.E., and Yergey A. Org. Lett. 4 (2002) 3191-3194
6. Seelig B., and Jäschke A. Tetrahedron Lett. 38 (1997) 7729-7732
7. Fruk L., Grondin A., Smith W.E., and Graham D. Chem. Commun. 18 (2002) 2100-2101
8. Graham D., Grondin A., McHugh C., Fruk L., and Smith W.E. Tetrahedron Lett. 43 (2002) 4785-4788
9. Hill K.W., Taunton-Rigby J., Carter J.D., Kropp E., Vagle K., Pieken W., McGee D.P., Husar G.M., Leuck M., Anziano D.J., and Sebesta D.P. J. Org. Chem. 66 (2001) 5352-5358
10. Hausch F., and Jäschke A. Nucleic Acids Res. 28 (2000) e35
11. Tona R., and Häner R. Bioconjugate Chem. 16 (2005) 837-842
12. Latham-Timmons H.A., Wolter A., Roach J.S., Giare R., and Leuck M. Nucleosides Nucleotides Nucl. 22 (2003) 1495-1497
13. Houseman B.T., and Mrksich M. Chem. Biol. 40 (2001) 443-454
14. Houseman B.T., Huh J.H., Kron S.J., and Mrksich M. Nature Biotechnol. 20 (2002) 270-274
15. Lindström U.M. Chem. Rev. 102 (2002) 2751-2772
16. Otto S., and Engberts J.B.F.N. Org. Biomol. Chem. 1 (2003) 2809-2820
17. Zalipsky S. Adv. Drug Delivery Res. 16 (1995) 157-182
18. Yang Z.J., Wang J.H., Lu Q., Xu J.B., Kobayashi Y., Takakura T., Takimoto A., Yoshioka T., Lian C.G., Chen C.M., Zhang D.D., Zhang Y., Li S.K., Sun X.H., Tan Y.Y., Yagi S., Frenkel E.P., and Hoffman R.M. Cancer Res. 64 (2004) 6673-6678
19. Klibanov A.L., Karuyama K., Torchilin V.P., and Huang L. FEBS Lett. 268 (1990) 235-238
20. MacBeath G., Koehler A.N., and Schreiber S.L. Biomacromolecules 121 (1999) 1065-1070
21. Sauer J. Angew. Chem., Int. Ed. Engl. 5 (1966) 211-230
22. Sauer J., Lang D., and Mielert A. Angew. Chem., Int. Ed. Engl. 5 (1962) 268-269
23. 3) δ 7.60 (s, 1H), 7.17 (s, 1H), 6.43-6.36 (m, 1H), 6.23-6.21 (m, 1H), 6.17-6.03 (m, 1H), 4.52 (m, 1H), 4. 32 (s, 1H), 4.10 (s, 2H), 3.75-3.60 (m, 14H), 3.40 (m, 4H), 3.16 (m, 1H), 3.00-2.90 (m, 3H), 2.78-2.61 (m, 3H), 2.20 (m, 2H), 1.80-1.60 (m, 5H), 1.40 (m, 3H), 0.99 (t, J = 10.2 Hz, 2H).
24. 2O) δ 6.43-6.36 (m, 1H), 6.23-6.21 (m, 1H), 6.17-6.03 (m, 1H), 4. 60 (s, 1H), 4.36 (d, J = 7.8 Hz, 1H), 4.30 (d, J = 7.8 Hz, 1H), 4.00 (m, 2H), 3.91-3.40 (m, 26H), 3.38-3.24 (m, 10H), 2.92 (m, 2H), 2.66-2.61 (m, 2H).
25. Sun X.-L., Grande D., Baskaran S., Hason S.R., and Chaikof E.L. Biomacromoleules 3 (2002) 1065-1070
26. Graille M., Stura E.A., Corper A.L., Sutton B.J., Taussig M.J., Charbonnier J.B., and Silverman G.J. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 5399-5404
27. Gao D., McBean N., Schultz J.S., Yan Y., Mulchandani A., and Chen W. J. Am. Chem. Soc. 128 (2006) 676-677