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Volumn 71, Issue 14, 2006, Pages 5136-5143

Urea-, thiourea-, and guanidine-linked glycooligomers as phosphate binders in water

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOOLIGOMERS; PHOSPHATE BINDERS; PSEUDOAMIDE SEGMENTS; THIOUREA OLIGOMERS;

EID: 33745686023     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060360q     Document Type: Article
Times cited : (85)

References (62)
  • 3
    • 0000231821 scopus 로고    scopus 로고
    • Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, U.K.
    • (c) Seel, C.; de Mendoza, J. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 2, pp 519-552.
    • (1996) Comprehensive Supramolecular Chemistry , vol.2 , pp. 519-552
    • Seel, C.1    De Mendoza, J.2
  • 4
    • 0042952941 scopus 로고    scopus 로고
    • Carbohydrate-Nucleic Acid Interactions
    • Ernst, B., Hart, G. W., Sinay, P., Eds,; Wiley-VCH: Weinheim, Germany
    • Moser, H. E. Carbohydrate-Nucleic Acid Interactions. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds,; Wiley-VCH: Weinheim, Germany, 2000; Part I, Vol. 2, pp 1095-1124.
    • (2000) Carbohydrates in Chemistry and Biology , vol.2 , Issue.PART I , pp. 1095-1124
    • Moser, H.E.1
  • 6
    • 0030558248 scopus 로고    scopus 로고
    • (c) Hunziker, J. Chimia 1996, 50, 248-256.
    • (1996) Chimia , vol.50 , pp. 248-256
    • Hunziker, J.1
  • 8
    • 4143083511 scopus 로고    scopus 로고
    • Antitumor and Antimicrobial Glycoconjugates
    • Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Heidelberg, Germany
    • (e) Lindhorst, T. K. Antitumor and Antimicrobial Glycoconjugates. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Heidelberg, Germany, 2001; Part III, pp 2393-2439.
    • (2001) Glycoscience: Chemistry and Chemical Biology , Issue.PART III , pp. 2393-2439
    • Lindhorst, T.K.1
  • 12
    • 0012235012 scopus 로고    scopus 로고
    • Non-Sugar Glycomimetics
    • Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Heidelberg, Germany
    • (d) Wessel, H. P. Non-Sugar Glycomimetics. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Heidelberg, Germany, 2001; Part III, pp 2725-2752. For selected examples, see:
    • (2001) Glycoscience: Chemistry and Chemical Biology , Issue.PART III , pp. 2725-2752
    • Wessel, H.P.1
  • 18
    • 33745709497 scopus 로고    scopus 로고
    • note
    • The term "pseudoamide groups" is used here to designate functional groups containing the segment N-C(=X), where X represents a heteroatom.
  • 19
    • 0038511082 scopus 로고    scopus 로고
    • For recent reviews on the use of pseudoamide functionalities in anion complexation and sensing, see: (a) Choi, K.; Hamilton, A. D. Coord. Chem. Rev. 2003, 240, 101-110.
    • (2003) Coord. Chem. Rev. , vol.240 , pp. 101-110
    • Choi, K.1    Hamilton, A.D.2
  • 23
    • 1642374335 scopus 로고    scopus 로고
    • For examples of polypseudoamide-polyphosphate binding in the oligonucleotide field, see: (a) Mallikarjuna, P.; Bruice, T. C. J. Am. Chem. Sac. 2004, 126, 3736-3747.
    • (2004) J. Am. Chem. Sac. , vol.126 , pp. 3736-3747
    • Mallikarjuna, P.1    Bruice, T.C.2
  • 55
    • 0031781275 scopus 로고    scopus 로고
    • Titration experiments were followed by NMR spectroscopy. The authors kindly thank Dr. C. Hunter for providing the titration isotherm curve-fitting programs. These programs use a simplex procedure to fit the data to the appropriate binding model to yield the association constant, the bound chemical shift in the host-guest (HG) or host-guest-guest (HGG) complex and, if required, the free chemical shifts of the unbound species. For a detailed description of the fitting methods and equations, see: (a) Bisson, A. P.; Hunter, C. A.; Morales, J. C.; Young, K. Chem Eur. J. 1998, 4, 845-851.
    • (1998) Chem Eur. J. , vol.4 , pp. 845-851
    • Bisson, A.P.1    Hunter, C.A.2    Morales, J.C.3    Young, K.4
  • 58
    • 0001511660 scopus 로고
    • (b) Job, P. Ann. Chim. 1928, 9, 113-203.
    • (1928) Ann. Chim. , vol.9 , pp. 113-203
    • Job, P.1
  • 59
    • 33745695470 scopus 로고    scopus 로고
    • note
    • Even though these small constants can be determined rather precisely by NMR spectroscopy, their significance must be taken with care. A consequence of very weak complexing is that high concentrations of ligand are generally required to drive the equilibrium, which results in possible medium effects, e.g., the chemical shifts of the host and the complex might not be constant throughout the experimental concentration range. For a discussion on the suitability of NMR spectroscopy to determine association constants, see ref 20a. In any case, the observed experimental values clearly indicate much weaker phosphate complexation by the urea-linked pseudooligosaccharides as compared with the thiourea- or gunidinium-linked analogues.
  • 62
    • 0000805378 scopus 로고
    • The Guanidinium Group: Its Biological Role; Synthetic Analogues
    • Digas, H., Schmidtchen, F. P., Eds.; Springer: Heidelberg, Germany
    • (a) Hannon, C. L.; Anslyn, E. V. The Guanidinium Group: Its Biological Role; Synthetic Analogues. In Bioorganic Chemistry Frontiers; Digas, H., Schmidtchen, F. P., Eds.; Springer: Heidelberg, Germany, 1993; p 193.
    • (1993) Bioorganic Chemistry Frontiers , pp. 193
    • Hannon, C.L.1    Anslyn, E.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.