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Volumn 137, Issue 27, 2015, Pages 8668-8671

Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CHAINS; DISSOCIATION; INFRARED DEVICES; OPTICAL PROPERTIES; PROTEINS;

EID: 84937140141     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03573     Document Type: Article
Times cited : (69)

References (41)
  • 21
    • 0003825877 scopus 로고
    • Royal Society of Chemistry: Cambridge
    • Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991; pp 261-263.
    • (1991) Cyclophanes , pp. 261-263
    • Diederich, F.1
  • 35
    • 84947739432 scopus 로고    scopus 로고
    • We also characterized the association of control guest N1 with M2 in water. The naphthalene core of N1 has two attached oxygen atoms with similar spacing as the two oxygens in S3 and F1, but with much weaker hydrogen bond accepting ability. 1H NMR chemical shift data indicated threading of N1 by M2 (Figure S8), and ITC titration studies in water at 27 °C determined that a 1:1 complex was formed with K a = 7.7 ×103 M-1 δ H = -5.9 kcal/mol, and T δS = 0.8 kcal/mol (Figure S27). The change in guest from S3 (or F1) to N1 thus lowers the enthalpic driving force by ∼6 kcal/mol. It seems likely that part of this is due to the weaker hydrogen bonding of N1 with the four NH residues inside M2, although other factors presumably contribute since the structures of S3, F1, and N1 have different hydrophobic surface areas and hydration shells. For a recent discussion of these factors, see
    • We also characterized the association of control guest N1 with M2 in water. The naphthalene core of N1 has two attached oxygen atoms with similar spacing as the two oxygens in S3 and F1, but with much weaker hydrogen bond accepting ability. 1H NMR chemical shift data indicated threading of N1 by M2 (Figure S8), and ITC titration studies in water at 27 °C determined that a 1:1 complex was formed with K a = 7.7 ×103 M-1, δ H = -5.9 kcal/mol, and T δS = 0.8 kcal/mol (Figure S27). The change in guest from S3 (or F1) to N1 thus lowers the enthalpic driving force by ∼6 kcal/mol. It seems likely that part of this is due to the weaker hydrogen bonding of N1 with the four NH residues inside M2, although other factors presumably contribute since the structures of S3, F1, and N1 have different hydrophobic surface areas and hydration shells. For a recent discussion of these factors, see: Biedermann, F.; Nau, W. M.; Schneider, H. J. Angew. Chem., Int. Ed. 2014, 53, 11158
    • (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 11158
    • Biedermann, F.1    Nau, W.M.2    Schneider, H.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.