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Volumn , Issue 9, 2008, Pages 1517-1526

Amide, amino, hydroxy and aminopyridine groups as building blocks for carbohydrate receptors

Author keywords

Carbohydrates; Hydrogen bonds; Molecular recognition; Receptors; Supramolecular chemistry

Indexed keywords


EID: 42349114342     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701097     Document Type: Article
Times cited : (40)

References (54)
  • 1
    • 84891014181 scopus 로고    scopus 로고
    • For reviews, see: a, Eds, T. Schrader, A. D. Hamilton, Wiley-VCH, Weinheim, Germany
    • For reviews, see: a) A. P. Davis, T. D. James, in Functional Synthetic Receptors (Eds.: T. Schrader, A. D. Hamilton), Wiley-VCH, Weinheim, Germany, 2005, p. 45-109;
    • (2005) Functional Synthetic Receptors , pp. 45-109
    • Davis, A.P.1    James, T.D.2
  • 4
    • 35548943201 scopus 로고    scopus 로고
    • For some recent examples of receptors operating through noncovalent interactions, see: a
    • For some recent examples of receptors operating through noncovalent interactions, see: a) Y. Ferrand, M. P. Crump, A. P. Davis, Science 2007, 318, 619-622;
    • (2007) Science , vol.318 , pp. 619-622
    • Ferrand, Y.1    Crump, M.P.2    Davis, A.P.3
  • 30
    • 33749117446 scopus 로고    scopus 로고
    • Kluwer Academic Publishers, Dordrecht, The Netherlands
    • a) H. Lis, N. Sharon, Lectins, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2003;
    • (2003) Lectins
    • Lis, H.1    Sharon, N.2
  • 36
    • 6344253005 scopus 로고    scopus 로고
    • Our previous binding studies showed that 2-aminopyridines provide an excellent structural motif for binding carbohydrates, associated with the ability to form cooperative and bidentate hydrogen bonds with the sugar OH groups. See: a M. Mazik, W. Radunz, R. Boese, J. Org. Chem. 2004, 69, 7448-7462;
    • Our previous binding studies showed that 2-aminopyridines provide an excellent structural motif for binding carbohydrates, associated with the ability to form cooperative and bidentate hydrogen bonds with the sugar OH groups. See: a) M. Mazik, W. Radunz, R. Boese, J. Org. Chem. 2004, 69, 7448-7462;
  • 41
    • 0000970872 scopus 로고    scopus 로고
    • Anslyn and coworkers have exploited the 2-aminopyridine unit for binding of cyclohexanediols and -triols. See: C. Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
    • Anslyn and coworkers have exploited the 2-aminopyridine unit for binding of cyclohexanediols and -triols. See: C. Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
  • 42
    • 33947202577 scopus 로고    scopus 로고
    • The character of carbohydrate-aromatic interaction is still a subject of controversy; for recent discussions on the importance of carbohydrate-aromatic interactions, see: a G. Terraneo, D. Potenza, A. Canales, J. Jiménez-Barbero, K. K. Baldridge, A. Bernardi, J. Am. Chem. Soc. 2007, 129, 2890-2900;
    • The character of carbohydrate-aromatic interaction is still a subject of controversy; for recent discussions on the importance of carbohydrate-aromatic interactions, see: a) G. Terraneo, D. Potenza, A. Canales, J. Jiménez-Barbero, K. K. Baldridge, A. Bernardi, J. Am. Chem. Soc. 2007, 129, 2890-2900;
  • 44
    • 53949087968 scopus 로고    scopus 로고
    • For examples of CH-π interactions in the crystal structures of the complexes formed between artificial receptors and carbohydrates, see ref, 2q
    • [2q].
  • 45
    • 34250641915 scopus 로고    scopus 로고
    • Many biological interactions occur in enzyme pockets or in membranes, meaning that they occur in an environment with a lower dielectric constant than the bulk solvent. For this reason, many theoretical studies on different enzyme model systems have been performed in a medium with a lower dielectric constant (mostly ε = 5.7, corresponding to chlorobenzene). See, for example: a) K.-B. Cho, Y. Moreau, D. Kumar, D. A. Rock, J. P. Jones, S. Shaik, Chem. Eur. J. 2007, 13, 4103-4115;
    • Many biological interactions occur in enzyme pockets or in membranes, meaning that they occur in an environment with a lower dielectric constant than the bulk solvent. For this reason, many theoretical studies on different enzyme model systems have been performed in a medium with a lower dielectric constant (mostly ε = 5.7, corresponding to chlorobenzene). See, for example: a) K.-B. Cho, Y. Moreau, D. Kumar, D. A. Rock, J. P. Jones, S. Shaik, Chem. Eur. J. 2007, 13, 4103-4115;
  • 48
    • 0035932611 scopus 로고    scopus 로고
    • Recognition of neutral sugars in aqueous solution through noncovalent interactions remains an important challenge in artificial receptor chemistry; for some examples, see refs.[2a,2h,2n] and: a V. Král, O. Rusin, F. P. Schmidtchen, Org. Lett. 2001, 3, 873-876;
    • [2a,2h,2n] and: a) V. Král, O. Rusin, F. P. Schmidtchen, Org. Lett. 2001, 3, 873-876;
  • 53
    • 53949090730 scopus 로고    scopus 로고
    • The binding constants were determined in chloroform at 25°C by titration experiments. Dilution experiments show that receptors do not self-aggregate in the concentration range used. For each system at least three 1H NMR titrations were carried out; for each titration 15-20 samples were prepared; b) Error in a single Ka estimation was less than 10, c K11 corresponds to the 1:1 association constant, K21 corresponds to the 2:1 receptor-sugar association constant, K12 corresponds to the 1:2 receptor-sugar association constant. β21, K11 x K21, β21, K11 x K12
    • 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.