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Volumn 10, Issue 2, 2008, Pages 297-300

A terphenyl scaffold for π-stacked guanidinium recognition elements

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; CARBOXYLIC ACID; GUANIDINE; PROTEIN; TERPHENYL DERIVATIVE;

EID: 38749134521     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7027042     Document Type: Article
Times cited : (25)

References (23)
  • 14
    • 0842282173 scopus 로고    scopus 로고
    • Wavefunction, Inc, Irvine, CA
    • Spartan '04; Wavefunction, Inc.: Irvine, CA, 2004.
    • (2004) Spartan '04
  • 15
    • 0035798133 scopus 로고    scopus 로고
    • Hamilton has conducted a thorough study of dicarboxylate binding by a non-stacked receptor analogous to control host 4 but constructed using closely related 2-amino-1,3-imidazoline binding elements. Linton, B. R, Goodman, M. S, Fan, E, van Arman, S. A, Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319
    • Hamilton has conducted a thorough study of dicarboxylate binding by a non-stacked receptor analogous to control host 4 but constructed using closely related 2-amino-1,3-imidazoline binding elements. Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319.
  • 17
    • 38749104158 scopus 로고    scopus 로고
    • This does not rule out the formation of oligomeric n:n complexes, but the binding interactions of a single carboxylate group to receptor 3 on which oligomer formation would rely is extremely weak (K < 10 M-1) in the methanol/water mixtures employed here. We assume that the contribution of non-1:1 structures to the observed binding isotherms is negligible
    • -1) in the methanol/water mixtures employed here. We assume that the contribution of non-1:1 structures to the observed binding isotherms is negligible.
  • 18
    • 38749120171 scopus 로고    scopus 로고
    • The exchangeable guanidinium protons that participate directly in hydrogen bonding are not observed in the deuterated aqueous mixtures used here. In these systems, the chemical shifts of the observable neighboring methylene protons are inherently small even for strong binding events, leading us to set a lower limit of 20 M-1 for binding constant determination in this setting
    • -1 for binding constant determination in this setting.
  • 21
    • 38749091602 scopus 로고    scopus 로고
    • The proximity of guanidinium and aromatic elements in 3 is supported by modeling and by upfield chemical shifts (∼0.3 ppm in DMSO; see Supporting Information) of guanidinium NH protons in 3 relative to those in 4. Determining the exact structure of the guanidinium-aromatic interactions of 3 and related compounds in aqueous media will be the focus of future work.
    • The proximity of guanidinium and aromatic elements in 3 is supported by modeling and by upfield chemical shifts (∼0.3 ppm in DMSO; see Supporting Information) of guanidinium NH protons in 3 relative to those in 4. Determining the exact structure of the guanidinium-aromatic interactions of 3 and related compounds in aqueous media will be the focus of future work.
  • 22
    • 35148895470 scopus 로고    scopus 로고
    • Marcus, Y. Chem. Rev. 2007, 107, 3880-3897.
    • (2007) Chem. Rev , vol.107 , pp. 3880-3897
    • Marcus, Y.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.