Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose

Tetrahedron

Volumn 65, Issue 22, 2009, Pages 4356-4366

  Fettke, Anja ^a   Peikow, Dirk ^a   Peter, Martin G ^a   Kleinpeter, Erich ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

1H NMR spectroscopy; Carbohydrates; Conformational analysis; Molecular modeling; NOE; S Glycosides; Thiochitobiose

Indexed keywords

CHITIN DERIVATIVE; GLYCOMIMETIC DERIVATIVE; GLYCOSIDE; OLIGOSACCHARIDE; THIAZOLINE; THIOCHITOBIOSE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CALCULATION; CONFORMATIONAL TRANSITION; ENZYME ACTIVITY; HYDROGEN BOND; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; SYNTHESIS;

EID: 65249138869     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.067     Document Type: Article

References (64)

1. Semino C.E., and Allende M.L. Int. J. Dev. Biol. 44 (2000) 183
2. van der Holst P.P.G., Schlaman H.R.M., and Spaink H.P. Curr. Opin. Struct. Biol. 11 (2001) 608
3. Peter M.G. Biopolymers (2002), Wiley-VCH, Weinheim p 481
4. Ujita M., Sakai K., Hamazaki K., Yoneda M., Isomura S., and Hara A. Biosci. Biotechnol. Biochem. 67 (2003) 2402
5. Rao F.V., Houston D.R., Boot R.G., Aerts J., Sakuda S., and van Aalten D.M.F. J. Biol. Chem. 278 (2003) 20110
6. Fusetti F., von Moeller H., Houston D., Rozeboom H.J., Dijkstra B.W., Boot R.G., Aerts J., and van Aalten D.M.F. J. Biol. Chem. 277 (2002) 25537
7. Vinetz J.M., Dave S.K., Specht C.A., Brameld K.A., Xu B., Hayward R., and Fidock D.A. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 14061
8. Recklies A.D., White C., and Ling H. Biochem. J. 365 (2002) 119
9. van Aalten D.M.F., Komander D., Synstad B., Gaseidnes S., Peter M.G., and Eijsink V.G.H. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 8979
10. Germer A., Peter M.G., and Kleinpeter E. J. Org. Chem. 67 (2002) 6328
11. Houston D.R., Shiomi K., Arai N., Omura S., Peter M.G., Turberg A., Synstad B., Eijsink V.G.H., and van Aalten D.M.F. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 9127
12. Germer A., Klod S., Peter M.G., and Kleinpeter E. J. Mol. Model. 8 (2002) 231
13. Germer A., Mügge C., Peter M.G., Rottmann A., and Kleinpeter E. Chem.-Eur. J. 9 (2003) 1964
14. Eijsink V.G.H., Synstad B., Kolstad G., Gaseidnes S., Komander D., Houston D., Peter M.G., and van Aalten D.M.F. Adv. Chitin Sci. 6 (2002) 71
15. Vaaje-Kolstad G., Houston D.R., Rao F.V., Peter M.G., Synstad B., van Aalten D.M.F., and Eijsink V.G.H. Bioenergetics 1696 (2004) 103
16. Vaaje-Kolstad G., Vasella A., Peter M.G., Netter C., Houston D.R., Westereng B., Synstad B., Eijsink V.G.H., and van Aalten D.M.F. J. Biol. Chem. 279 (2004) 3612
17. Cederkvist F., Zamfir A.D., Bahrke S., Eijsink V.G.H., Sorlie M., Peter-Katalinic J., and Peter M.G. Angew. Chem., Int. Ed. 45 (2006) 2429
18. Thiele G., Rottmann A., Germer A., Kleinpeter E., Spindler K.D., Synstad B., Eijsink V.G.H., and Peter M.G. J. Carbohydr. Chem. 21 (2002) 471
19. Wang L.X., and Lee Y.C. J. Chem. Soc., Perkin Trans. 1 (1996) 581
20. Montero E., Garcia-Herrero A., Asensio J.L., Hirai K., Ogawa S., Santoyo-González F., Cañada F.J., and Jiménez-Barbero F.J. Eur. J. Org. Chem. 10 (2000) 1945
21. Bock K., Duus J.O., and Refn S. Carbohydr. Res. 253 (1994) 51
22. Aguilera B., Jiménez-Barbero F.J., and Fernández-Mayoralas A. Carbohydr. Res. 308 (1998) 19
23. Raimbaud E., Buléon A., and Pérez S. Carbohydr. Res. 227 (1992) 351
24. Tsai C.S., Reyes-Zamora C., and Otson R. Biochim. Biophys. Acta 250 (1971) 172
25. Paul B., and Korytnyk W. Carbohydr. Res. 126 (1984) 27
26. Barr B.K., and Holewinski R.J. Biochemistry 41 (2002) 4447
27. Coutinho P.M., and Henrissat B. In: Gilbert H.J., Davies G., Henrissat B., and Svensson B. (Eds). Recent Advances in Carbohydrate Bioengineering (1999), The Royal Society of Chemistry, Cambridge 3. http://www.cazy.org See also: Carbohydrate Active Enzymes database (URL: http://www.cazy.org/)
28. Mark B.L., Vocadlo D.J., Knapp S., Triggs-Raine B.L., Withers S.G., and James M.N.G. J. Biol. Chem. 276 (2001) 10330
29. Tews I., Perrakis A., Oppenheim A., Dauter Z., Wilson K., and Vorgais C. Nat. Struct. Biol. 3 (1996) 638
30. Lillelund V.H., Jemnsen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515
31. Terwisscha van Scheltinga A.C., Armand S., Kalk K.H., Isogai A., Henrissat B., and Dijkstra B.W. Biochemistry 34 (1995) 15619
32. Tews I., Terwisscha van Scheltinga A.C., Perrakis A., Wilson K.S., and Dijkstra B.W. J. Am. Chem. Soc. 119 (1997) 7954
33. Peters T., and Pinto B. Curr. Opin. Struct. Biol. 6 (1996) 710
34. Cumming D., and Carver J. Biochemistry 26 (1987) 6664
35. Tanaka M., Kyosaka S., and Sekiguchi Y. Chem. Pharm. Bull. 24 (1976) 3144
36. Tanaka M., Kyosaka S., and Ito Y. Chem. Pharm. Bull. 21 (1973) 1971
37. Micheel F., van de Kamp F.P., and Petersen H. Chem. Ber. 90 (1957) 521
38. Horton D., and Wolfrom M.L. J. Org. Chem. 27 (1962) 1794
39. Zemplén G. Ber. Dtsch. Chem. Ges. 60 (1927) 1555
40. Cava M.P., and Levinson M.I. Tetrahedron 41 (1985) 5061
41. Jesberger M., Davis T.P., and Barner L. Synthesis 13 (2003) 1929
42. Peikow, D. Synthese und Glycosidasehemmung von Thio-analogen Kohlenhydraten PhD-thesis; University of Potsdam, 2006, URL: http://opus.kobv.de/ubp/volltexte/2006/1119/.
43. Gronenborn A.M., and Clore G.M. Nucl. Magn. Reson. Spectrosc. 17 (1985) 1
44. Woods R., Dwek R., Edge C., and Fraser-Reid B. J. Phys. Chem. 99 (1995) 3832
45. Atkins P., and de Paula J. Physikalische Chemie. 4th ed. (2006), VCH, Weinheim
46. Gerlt J., and Youngblood A. J. Am. Chem. Soc. 102 (1980) 7433
47. Manor P., Saenger W., Davies D., Janowski K., and Rabczenko A. Biochim. Biophys. Acta 340 (1974) 472
48. Wu G., Serianni A., and Baker R. J. Org. Chem. 48 (1983) 1750
49. Nishida Y., Hori H., Ohuri H., and Meguro H. J. Carbohydr. Chem. 7 (1988) 239
50. Nishida Y., Hori H., Ohuri H., and Meguro H. Carbohydr. Res. 170 (1987) 106
51. Espionosa J.F., Asensio J., Bruix M., and Jiménez-Barbero F.J. J. An. Quim. 92 (1996) 320
52. Muñoz J.L., Garcia-Herrero A., Asensio J.L., Auzennaeau F.I., Cañada F.J., and Jiménez-Barbero F.J. J. Chem. Soc., Perkin Trans. 1 (2001) 867
53. Leeflang B., Vliegenhardt J., Kroon-Batenburg L., van Eijck B., and Kroon J. Carbohydr. Res. 230 (1992) 41
54. Dowd M., French A., and Reilly P. Carbohydr. Res. 233 (1992) 15
55. Engelsen S., Perez S., Braccini I., and Herve du Pont C. J. Comput. Chem. 16 (1995) 1096
56. Mo F. Acta Chem. Scand. A33 (1979) 207
57. SYBYL. Molecular Modeling Software (2004), TRIPOS, St. Louis, MO
58. Reiling S., Schlenkrich M., and Brickmann J. J. Comput. Chem. 17 (1996) 450
59. Glennon T., and Merz Jr. K. J. Mol. Struct. 395-396 (1997) 157
60. Cornell W., Cieplak P., Bayly C., Gould I., Merz K., Ferguson D., Spellmeyer D., Fox T., Caldwell J., and Kollmann P. J. Am. Chem. Soc. 117 (1995) 5179
61. Glycam Parameters from http://glycam.ccrc.uga.edu/documents/gl_params.html.
62. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.03 (2003), Gaussian, Pittsburgh, PA
63. Bayly C.I., Cieplak P., Cornell W.D., and Kollman P.A. J. Phys. Chem. 97 (1993) 10269
64. Cornell W.D., Cieplak P., Bayly C.I., and Kollman P.A. J. Am. Chem. Soc. 115 (1993) 9620