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Volumn 72, Issue 24, 2007, Pages 9032-9045

Multi-mannosides based on a carbohydrate scaffold: Synthesis, force field development, molecular dynamics studies, and binding affinities for lectin con A

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; BINDING SITES; CARBOHYDRATES; GRAFTING (CHEMICAL); MOLECULAR DYNAMICS; SCAFFOLDS; SYNTHESIS (CHEMICAL);

EID: 36649010822     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071248a     Document Type: Article
Times cited : (73)

References (96)
  • 5
    • 11544358874 scopus 로고    scopus 로고
    • For reviews on lectins: a
    • For reviews on lectins: (a) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674.
    • (1998) Chem. Rev , vol.98 , pp. 637-674
    • Lis, H.1    Sharon, N.2
  • 69
    • 0034630834 scopus 로고    scopus 로고
    • Formation of soluble aggregates between Con A and rigid oligomannosides has been observed. However, in solution, lectin recruitement should be reflected in activation, rather than inhibition, of the association of the lectin to the reference mannan fixed in the microplate well surface upon addition of the multi-valent ligands, resulting in abnormal inhibition curves, which was not the present case. See: (a) Burke, S. D.; Zhao, Q.; Schuster, C.; Kiessling, L. L. J. Am. Chem. Soc. 2000, 122, 4518-4519.
    • Formation of soluble aggregates between Con A and rigid oligomannosides has been observed. However, in solution, lectin recruitement should be reflected in activation, rather than inhibition, of the association of the lectin to the reference mannan fixed in the microplate well surface upon addition of the multi-valent ligands, resulting in abnormal inhibition curves, which was not the present case. See: (a) Burke, S. D.; Zhao, Q.; Schuster, C.; Kiessling, L. L. J. Am. Chem. Soc. 2000, 122, 4518-4519.
  • 72
    • 0028325299 scopus 로고    scopus 로고
    • Con A is known to possess an extended binding site for the Manp-a(1 → 3)-[Manp-a(1 → 6)]-Man trisaccharide core. See: (a) Mandal, D. K.; Battachariyya, L.; Koening, S. H.; Brown, R. D., III; Oscarson, S.; Brewer, C. F. Biochemistry 1994, 33, 1157.
    • Con A is known to possess an extended binding site for the Manp-a(1 → 3)-[Manp-a(1 → 6)]-Man trisaccharide core. See: (a) Mandal, D. K.; Battachariyya, L.; Koening, S. H.; Brown, R. D., III; Oscarson, S.; Brewer, C. F. Biochemistry 1994, 33, 1157.
  • 83
    • 33750513038 scopus 로고    scopus 로고
    • Automatic and Highly Reproducible RESP and ESP Charge Derivation: Application to the Development of Programs RED and X RED
    • Anaheim, CA, March 28 to April 1, ACS: Washington, DC
    • Pigache, A.; Cieplak, P.; Dupradeau, F.-Y. Automatic and Highly Reproducible RESP and ESP Charge Derivation: Application to the Development of Programs RED and X RED, 227th ACS National Meeting, Anaheim, CA, March 28 to April 1, 2004; ACS: Washington, DC, 2004.
    • (2004) 227th ACS National Meeting
    • Pigache, A.1    Cieplak, P.2    Dupradeau, F.-Y.3
  • 84
    • 36649006377 scopus 로고    scopus 로고
    • RRMS (relative root mean square value between MEP calculated by quantum mechanics and that generated using the derived charge values) of 0.126 was obtained for the fit. Intra-molecular charge constraints, intermolecular charge constraints, charge value equivalencing between the different molecular orientations and conformations, and the hyperbolic constraint of the restrained fit are accountable for an increase of 0.005, 0.003, 0.010, and 0.006 of the RRMS value, respectively. These values rigorously demonstrate the strength and weakness of the approach followed. The RESP charge derivation procedure was automatically carried out using the RESP ESP charge Derive (R.E.D, program (http://q4md-forcefieldtools.org/RED/).41 The RESP atom charge values and FFTPDB were submitted in the RESP ESP charge DDataBase (R.E.DD.B, ) and are available as the F-71 R.E.DD.B. project code as a suite of files in the Tripos mol2 file format cons
    • 41 The RESP atom charge values and FFTPDB were submitted in the RESP ESP charge DDataBase (R.E.DD.B.) (http://q4md-forcefieldtools.org/REDDB/) and are available as the "F-71" R.E.DD.B. project code as a suite of files in the Tripos mol2 file format considered as force field library precursors (http://www.tripos.com/ index.php?family=modules,-SimplePage,,,&page=sup_mol2&s=0).
  • 87
    • 36649035857 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc, Pittsburgh, PA, 1998
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998.


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