Modulation of flavin recognition and redox properties through donor atom-π interactions

Journal of the American Chemical Society

Volumn 120, Issue 34, 1998, Pages 8606-8609

  Breinlinger, Eric C ^a   Keenan, Christopher J ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVINE NUCLEOTIDE;

ARTICLE; ELECTRON TRANSPORT; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; OXIDATION REDUCTION REACTION;

EID: 0032475447     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9809556     Document Type: Article

References (36)

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22. Electrostatic potential maps were generated from B3LYP 6-31G* density functional calculations (Gaussian '94, Gaussian, Inc.) using the Spartan V4.1 graphics package (Wavefunction Inc.). We have recently demonstrated the the applicability of the B3LYP hybrid wave function to hydrogen-bonding and redox processes of analogous host - guest systems.
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24. All compounds appearing in this study have been characterized by high-resolution mass, NMR, and IR spectroscopies.
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27. Association constants determined for a 1:1 binding process of receptors with flavin using these two methods are equivalent: Tamura, N.; Mitsui, K.; Nabeshima, T.; Yano, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2229-2237.
28. 2) chosen due to their attributes for NMR and electrochemical experiments, respectively. It was found that the presence of carrier electrolyte does not affect the association constants.
29. Ethyl receptor 4a was chosen to diminish the possible effect of dispersion interactions on recognition.
30. 11 indicate the possibility of a donor - π interaction for 3b, providing an explanation for the slightly enhanced recognition of flavin 1 for this receptor.
31. 19F signal for receptor 4a on binding with flavin was further evidence of the proximity of donor atom to the flavin nucleus: (a) Macheroux, P.; Kojiro, C.; Schopfer, L.; Chakraborty, S.; Massey, V. Biochemistry, 1990, 29, 2670-2679. (b) Miura, R. J. Biochem. 1989, 105, 318-322.
32. 19F signal for receptor 4a on binding with flavin was further evidence of the proximity of donor atom to the flavin nucleus: (a) Macheroux, P.; Kojiro, C.; Schopfer, L.; Chakraborty, S.; Massey, V. Biochemistry, 1990, 29, 2670-2679. (b) Miura, R. J. Biochem. 1989, 105, 318-322.
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34. Referenced to ferrocene as an external standard: Gagné, R.; Koval, C. Lisensky, G. C. Inorg. Chem, 1980, 19, 2854.
35. 1/2 values are ±3 mV.
36. rad - interaction on the mechanism of the monoamine oxidases.