Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1719-1721

  Balcerzak, Anna K ^a   Ferreira, Sandra S ^a   Trant, John F ^a   Ben, Robert N ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

AFGP; Antifreeze glycoproteins; Carbohydrate hydration; Ice recrystallization inhibition; Thermal hysteresis

Indexed keywords

ANTIFREEZE GLYCOPROTEIN; ANTIFREEZE PROTEIN; DISACCHARIDE; GLYCOPROTEIN; ICE; MONOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION;

EID: 84856658487     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.097     Document Type: Article

References (24)

1. Yeh, Y.; Feeney, R. E. Chem. Rev. 1996, 96, 601.
2. DeVries, A. L. Science 1971, 172, 1152.
3. DeVries, A. L.; Wohlschlag, D. E. Science 1969, 163, 1073.
4. DeVries, A. L.; Komatsu, S. K.; Feeney, R. E. J. Biol. Chem. 1970, 245, 2901.
5. Harding, M. M.; Anderberg, P. I.; Haymet, A. D. J. Eur. J. Biochem. 2003, 270, 1381.
6. DeVries, A. L.; Vandenheede, J.; Feeney, R. E. J. Biol. Chem. 1971, 246, 305.
7. Knight, C. A.; Duman, J. G. Cryobiology 1986, 23, 256.
8. Wang, T.; Zhu, Q.; Yang, X.; Layne, J. R., Jr.; Devries, A. L. Cryobiology 1994, 31, 185.
9. Jun-Hui, W. Cryobiology 2000, 41, 1.
10. Rubinsky, B.; Arav, A.; Devries, A. L. Cryobiology 1992, 29, 69.
11. Raymond, J. A.; DeVries, A. L. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 2589.
12. Czechura, P.; Tam, R. Y.; Dimitrijevic, E.; Murphy, A. V.; Ben, R. N. J. Am. Chem. Soc. 2008, 130, 2928.
13. Tachibana, Y.; Matsubara, N.; Nakajima, F.; Tsuda, T.; Tsuda, S.; Monde, K.; Nishimura, S.-I. Tetrahedron 2002, 58, 10213.
14. Tachibana, Y.; Fletcher, G. L.; Fujitani, N.; Tsuda, S.; Monde, K.; Nishimura, S.-I. Angew. Chem. Int. Ed. 2004, 43, 856.
15. Tam, R. Y.; Ferreira, S. S.; Czechura, P.; Chaytor, J. L.; Ben, R. N. J. Am. Chem. Soc. 2008, 130, 17494.
16. Chaytor, J. L.; Ben, R. N. Bioorg. Med. Chem. Lett. 2010, 20, 5251.
17. Bouvet, V. R.; Ben, R. N. J. Org. Chem. 2005, 71, 3619.
18. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press Ltd: Oxford, 1983. p 83.
19. Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244.
20. King, J. F.; Allbutt, A. D. Can. J. Chem. 1969, 47, 1445.
21. King, J. F.; Allbutt, A. D. Can. J. Chem. 1970, 48, 1754.
22. Knight, C. A.; Hallett, J.; DeVries, A. L. Cryobiology 1988, 25, 55.
23. Jackman, J.; Noestheden, M.; Moffat, D.; Pezacki, J. P.; Findlay, S.; Ben, R. N. Biochem. Biophys. Res. Commun. 2007, 354, 340.
24. Chaytor, J. L.; Tokarew, J. M.; Wu, L. K.; Leclère, M.; Tam, R. Y.; Capicciotti, C. J.; Guolla, L.; von Moos, E.; Findlay, C. S.; Allan, D. S.; Ben, R. N. Glycobiology 2012, 22, 123.