Recognition Properties of Flavin Analogues with Bile Acid-Based Receptors: Role of Steric Effects in Hydrogen Bond Based Molecular Recognition

Prosenjit Chattopadhyay; Rekha Nagpal; Pramod S. Pandey

doi:10.1071/CH07342

RESEARCH ARTICLE

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Recognition Properties of Flavin Analogues with Bile Acid-Based Receptors: Role of Steric Effects in Hydrogen Bond Based Molecular Recognition

Prosenjit Chattopadhyay ^A , Rekha Nagpal ^A and Pramod S. Pandey ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi-110016, India.

^B Corresponding author. Email: pramod@chemistry.iitd.ac.in

Australian Journal of Chemistry 61(3) 216-222 https://doi.org/10.1071/CH07342
Submitted: 26 September 2007 Accepted: 24 January 2008 Published: 26 March 2008

Abstract

The recognition properties of 7,8-dimethyl flavin analogues by bile acid-based receptors that contain 2,6-diaminopyridine and the dioctylamide of 2,6-diaminopyridine in CHCl₃ were determined. The results show that the bile acid-based receptors bind 7,8-dimethyl flavin analogues less effectively as compared to 7,8-unsubstituted flavins reported earlier, which is contrary to the known fact that the association constants increase with increasing electron-donating capacity of the substituents at the 7 and 8 positions of the flavin analogues.

Acknowledgements

The authors are thankful to the Council of Scientific and Industrial Research, New Delhi, and the University Grants Commission, New Delhi for research fellowships to P.C. and R.N., respectively. The authors thank Shailesh Upreti and M. Senthil Kumar for helpful discussions. The authors also thank the Department of Science and Technology, New Delhi for funding a single crystal diffractometer under FIST to the Department of Chemistry, IIT Delhi, India.

References

^* Single-crystal diffraction study was carried out on a Bruker Smart Apex CCD diffractometer with a Mo K_α (λ = 0.71073 Å) sealed tube. The crystal structure was solved by direct methods and refined using the SHELXTL package.^[⁸^] All hydrogen atoms were included in idealized positions, and a riding model was used. Non-hydrogen atoms were refined with anisotropic displacement parameters.

Recognition Properties of Flavin Analogues with Bile Acid-Based Receptors: Role of Steric Effects in Hydrogen Bond Based Molecular Recognition

Abstract

Acknowledgements

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