Foldamer-based molecular recognition

Journal of the American Chemical Society

Volumn 122, Issue 12, 2000, Pages 2758-2762

  Prince, Ryan B ^a   Barnes, Stephanie A ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SOLVENT;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFORMATION; MOLECULAR RECOGNITION; MOLECULE; STEREOCHEMISTRY; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY;

EID: 0034728690     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993830p     Document Type: Article

References (31)

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24. All measurements were presumed to be at equilibrium since the observations were independent of time (spectra were measured 10 min after preparation, then again 24 h later).
25. 3 solvent), no binding of the guests was observed, as evidenced by the absence of a CD signal.
26. 1I or the stoichiometry.
27. Oligomer 1 is not appreciably soluble in pure water.
28. Upon addition of (+)-α-pinene (30 equiv) to a solution containing 1 and (-)-α-pinene (30 equiv), no change was observed in the CD signal (θ = 0 mdeg), indicating that the formation of the complexes was a reversible process that reached equilibrium in 15 s.
29. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley & Sons: New York, 1987.
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31. Molecular modeling was performed using MacroModel 5.5 (OPLS force field). Complexes of the right-handed helical conformation of 1 and the enantiomers of α-pinene resulted in a more stable complex with (+)-α-pinene. The Monte Carlo search explored the rotation and translation of α-pinene with respect to 1. All atoms of 1 and α-pinene were free to move during the minimizations. The redundancy of the lowest energy complexes and the independence of the starting point were evidence for converged searches.