GlcNAc-Thiazoline conformations

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 5, 2009, Pages 1831-1836

  Knapp, Spencer ^a   Fash, David ^a   Abdo, Mohannad ^a   Emge, Thomas J ^a   Rablen, Paul R ^b  

^a RUTGERS UNIVERSITY   (United States)

^b SWARTHMORE COLLEGE   (United States)

Author keywords

Ab initio calculations; Enzyme inhibitors; Mitsunobu reaction; NOE

Indexed keywords

BETA N ACETYLHEXOSAMINIDASE; BETA N ACETYLHEXOSAMINIDASE INHIBITOR; ENZYME INHIBITOR; N ACETYLGLUCOSAMINE; N ACETYLGLUCOSAMINE THIAZOLINE DERIVATIVE; PYRANOSE; REAGENT; TETRADECANOATE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL REACTION; CORRELATION ANALYSIS; DRUG BINDING; DRUG CONFORMATION; DRUG STRUCTURE; ENZYME ACTIVE SITE; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

BETA-N-ACETYLHEXOSAMINIDASES; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; GLUCOSAMINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; THERMODYNAMICS; THIAZOLES;

EID: 61349085584     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.066     Document Type: Article

References (33)

1. Tews I., Perrakis A., Oppenheim A., Dauter Z., Wilson K.S., and Vorgias C.E. Nat. Struct. Biol. 3 (1996) 638
2. Tews I., Terwisscha van Scheltinga A.C., Perrakis A., Wilson K.S., and Dijkstra B.W. J. Am. Chem. Soc. 119 (1997) 7954
3. Mark B.L., Wasney G.A., Salo T.J., Khan A.R., Cao Z., Robbins P.W., James M.N.G., and Triggs-Raine B.L. J. Biol. Chem. 273 (1998) 19618
4. Drouillard S., Armand S., Davies G.J., Vorgias C.E., and Henrissat B. Biochem. J. 328 (1997) 945
5. Knapp S., Vocadlo D., Gao Z., Kirk B., Lou J., and Withers S.G. J. Am. Chem. Soc. 118 (1996) 6804
6. 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
7. Macauley M.S., Whitworth G.E., Debowski A.W., Chen D., and Vocadlo D.J. J. Biol. Chem. 280 (2005) 25313
8. Whitworth G.E., Macauley M.S., Stubbs K.A., Dennis R.J., Taylor E.J., Davies G.J., Greig I.R., and Vocadlo D.J. J. Am. Chem. Soc. 129 (2007) 635
9. Dennis R.J., Taylor E.J., Macauley M.S., Stubbs K.A., Turkenburg J.P., Hart S.J., Black G.N., Vocadlo D.J., and Davies G.J. Nat. Struct. Mol. Biol. 13 (2006) 365
10. Mark B.L., Mahuran D.J., Cherney M.M., Zhao D., Knapp S., and James M.N.G. J. Mol. Biol. 327 (2003) 1093
11. Maier T., Strater N., Schuette C.G., Klingenstein R., Sandhoff K., and Saenger W. J. Mol. Biol. 328 (2003) 669
12. Langley D.B., Harty D.W.S., Jacques N.A., Hunter N., Guss J.M., and Collyer C.A. J. Mol. Biol. 377 (2008) 104
13. See discussion in:. Silverman R.B. The Organic Chemistry of Drug Design and Drug Action. 2nd ed. (2004), Elsevier Academic Press, Amsterdam, The Netherlands pp 152-172
14. For a discussion in the area of HIV inhibition, see:. Das K., Lewi P.J., Hughes S.H., and Arnold E. Prog. Biophys. Mol. Biol. 88 (2005) 209
15. Knapp S., Abdo M., Ajayi K., Huhn R.A., Emge T.J., Kim E.J., and Hanover J.A. Org. Lett. 9 (2007) 2321
16. Amorelli B., Yang C., Rempel B., Withers S.G., and Knapp S. Bioorg. Med. Chem. Lett. 18 (2008) 2944
17. 3 crosspeak observed for 1 (Table 3) might represent a minor contribution from this dimer. However, this crosspeak persisted without variation upon two- and fourfold dilution, consistent with an intramolecular through-space contact.
18. 6 bond were separately considered, and the lowest energy conformer selected for further analysis.
19. Foces-Foces C., Cano F.H., Bernabe M., Penades S., and Martin-Lomas M. Carbohydr. Res. 135 (1984) 1
20. Pauling L. Nature 161 (1948) 707
21. 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.; Bakken, V.; 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 C.02: Gaussian, Inc., Wallingford CT, 2004.
22. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
23. Becke A.D. J. Chem. Phys. 98 (1993) 5648
24. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
25. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
26. Foresman J.B., and Frisch A. Exploring Chemistry with Electronic Structure Methods (1996), Gaussian, Pittsburgh
27. London F. J. Phys. Radium 8 (1937) 397
28. Ditchfield R. Mol. Phys. 27 (1974) 789
29. Wolinski K., Hilton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
30. Rablen P.R., Pearlman S.A., and Finkbiner J. J. Phys. Chem. A 103 (1999) 7357
31. Helgaker T., Watson M., and Handy N.C. J. Chem. Phys. 113 (2000) 9402
32. Sychrovsky V., Gräfenstein J., and Cremer D. J. Chem. Phys. 113 (2000) 3530
33. Barone V., Peralta J.E., Contreras R.H., and Snyder J.P. J. Phys. Chem. A 106 (2002) 5607