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Research on Chemical Intermediates

, Volume 39, Issue 1, pp 371–383 | Cite as

Chiral recognition and supramolecular photoreaction of 1,1′-binaphthol with bovine and human serum albumins

  • Masaki Nishijima
  • Jae-Won Chang
  • Cheng Yang
  • Gaku Fukuhara
  • Tadashi Mori
  • Yoshihisa Inoue
Article

Abstract

In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1′-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.

Keywords

Chiral photochemistry Serum albumin Binaphthol Supramolecular photochirogenesis 

Notes

Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (A) (no. 21245011; YI) and (B) (no. 23350018; TM) from the Japan Society for the Promotion of Science, and a Grant for Basic Science Research from The Sumitomo Foundation (no. 080435; MN), which are gratefully acknowledged.

References

  1. 1.
    Y. Inoue, Asymmetric photochemical reactions in solution. Chem. Rev. 92, 741–770 (1992)CrossRefGoogle Scholar
  2. 2.
    Y. Inoue, Synthetic chemistry: light on chirality. Nature 436, 1099–1100 (2005)CrossRefGoogle Scholar
  3. 3.
    Y. Inoue, V. Ramamurthy, Chiral Photochemistry (Marcel Dekker, New York, 2004)Google Scholar
  4. 4.
    A. Nakamura, Y. Inoue, Supramolecular catalysis of the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate by γ-cyclodextrin. J. Am. Chem. Soc. 125, 966–972 (2003)CrossRefGoogle Scholar
  5. 5.
    A. Nakamura, Y. Inoue, Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate within γ-cyclodextrin cavity through chemical modification. Inverted product distribution and enhanced enantioselectivity. J. Am. Chem. Soc. 127, 5338–5339 (2005)CrossRefGoogle Scholar
  6. 6.
    C. Yang, G. Fukuhara, A. Nakamura, Y. Origane, K. Fujita, D.-Q. Yuan, T. Mori, T. Wada, Y. Inoue, Enantiodifferentiating [4 + 4]photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X-diamino-6A,6X-dideoxy-γ-cyclodextrins: manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesis. J. Photochem. Photobiol. A: Chem. 173, 375–383 (2005)CrossRefGoogle Scholar
  7. 7.
    C. Yang, A. Nakamura, T. Wada, Y. Inoue, Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a flexible or rigid cap. Org. Lett. 8, 3005–3008 (2006)CrossRefGoogle Scholar
  8. 8.
    C. Ke, C. Yang, W. Liang, T. Mori, Y. Liu, Y. Inoue, Critical stereocontrol by inter-amino distance of supramolecular photocyclodimerization of 2-anthracenecarboxylate mediated by 6-(O-aminoalkylamino)-γ-cyclodextrins. New J. Chem. 34, 1323–1329 (2010)CrossRefGoogle Scholar
  9. 9.
    A. Joy, V. Ramamurthy, J.R. Scheffer and D.R. Corbin, Enantioselective photoelectrocyclization within zeolites: tropolone methyl ether in chirally modified NaY, Chem. Commun. 1379–1380 (1998)Google Scholar
  10. 10.
    A. Joy, J.R. Scheffer, V. Ramamurthy, Chirally modified zeolites as reaction media: photochemistry of an achiral tropolone ether. Org. Lett. 2, 119–121 (2000)CrossRefGoogle Scholar
  11. 11.
    J. Sivaguru, A. Natarajan, L.S. Kaanumalle, J. Shailaja, S. Uppili, A. Joy, V. Ramamurthy, Asymmetric photoreactions within zeolites: role of confinement and alkali metal ions. Acc. Chem. Res. 36, 509–521 (2003)CrossRefGoogle Scholar
  12. 12.
    Y. Kawanami, T.C.S. Pace, J. Mizoguchi, T. Yanagi, M. Nishijima, T. Mori, T. Wada, C. Bohne, Y. Inoue, Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates. J. Org. Chem. 74, 7908–7921 (2009)CrossRefGoogle Scholar
  13. 13.
    T. Bach, H. Bergmann, B. Grosch, K. Harms, Highly enantioselective intra- and intermolecular [2 + 2] photocycloaddition reactions of 2-quinolones mediated by a chiral lactam host: host-guest interactions, product configuration, and the origin of the stereoselectivity in solution. J. Am. Chem. Soc. 124, 7982–7990 (2002)CrossRefGoogle Scholar
  14. 14.
    B. Grosch, C.N. Orlebar, E. Herdtweck, W. Massa, T. Bach, Highly enantioselective Diels-Alder reaction of a photochemically generated o-quinodimethane with olefins. Angew. Chem. Int. Ed. 42, 3693–3696 (2003)CrossRefGoogle Scholar
  15. 15.
    M. Fleck, C. Yang, T. Wada, Y. Inoue and T. Bach, Regioselective [2 + 2]-photocycloaddition reactions of chiral tetronates-influence of temperature, pressure, and reaction medium, Chem. Commun. 4422 (2007)Google Scholar
  16. 16.
    Y. Gao, T. Wada, K. Yang, K. Kim, Y. Inoue, Supramolecular photochirogenesis in sensitizing chiral nanopore: enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by POST-1. Chirality 17, S19–S23 (2005)CrossRefGoogle Scholar
  17. 17.
    G. Fukuhara, T. Nakamura, C. Yang, T. Mori, Y. Inoue, Dual chiral, dual supramolecular diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to amylose scaffold. Org. Lett. 12, 3510–3513 (2010)CrossRefGoogle Scholar
  18. 18.
    G. Fukuhara, T. Nakamura, C. Yang, T. Mori, Y. Inoue, Diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to cellulose scaffold. J. Org. Chem. 75, 4307–4310 (2010)CrossRefGoogle Scholar
  19. 19.
    T. Wada, N. Sugahara, M. Kawano and Y. Inoue, First asymmetric photochemistry with nucleosides and DNA: enantiodifferentiating Z–E photoisomerization of cyclooctene, Chem. Lett. 1174–1175 (2000)Google Scholar
  20. 20.
    M. Zandomeneghi, Photochemical activation of racemic mixtures in biological matrices. J. Am. Chem. Soc. 113, 7774–7775 (1991)CrossRefGoogle Scholar
  21. 21.
    N. Levi-Minzi, M. Zandomeneghi, Photochemistry in biological matrices: activation of racemic mixtures and interconversion of enantiomers. J. Am. Chem. Soc. 114, 9300–9304 (1992)CrossRefGoogle Scholar
  22. 22.
    A. Ouchi, G. Zandomeneghi, M. Zandomeneghi, Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen. Chirality 14, 1–11 (2002)CrossRefGoogle Scholar
  23. 23.
    V. Lhiaubet-Vallet, Z. Sarabia, F. Bosca, M.A. Miranda, Human serum albumin-mediated stereodifferentiation in the triplet state behavior of (S)- and (R)-carprofen. J. Am. Chem. Soc. 126, 9538–9539 (2004)CrossRefGoogle Scholar
  24. 24.
    J. Rohacova, M.L. Marin, M.A. Miranda, Complexes between fluorescent cholic acid derivatives and human serum albumin. A photophysical approach to investigate the binding behavior. J. Phys. Chem. B 114, 4710–4716 (2010)CrossRefGoogle Scholar
  25. 25.
    M. Marin, V. Lhiaubet-Vallet, M.A. Miranda, Site-dependent photo-fries rearrangement within serum albumins. J. Phys. Chem. B 115, 2910–2915 (2011)CrossRefGoogle Scholar
  26. 26.
    T. Wada, M. Nishijima, T. Fujisawa, N. Sugahara, T. Mori, A. Nakamura, Y. Inoue, Bovine serum albumin-mediated enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate. J. Am. Chem. Soc. 125, 7492–7493 (2003)CrossRefGoogle Scholar
  27. 27.
    M. Nishijima, T. Wada, T. Mori, T.C.S. Pace, C. Bohne, Y. Inoue, Highly enantiomeric supramolecular [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by human serum albumin. J. Am. Chem. Soc. 129, 3478–3479 (2007)CrossRefGoogle Scholar
  28. 28.
    M. Nishijima, T.C.S. Pace, A. Nakamura, T. Mori, T. Wada, C. Bohne, Y. Inoue, Supramolecular photochirogenesis with biomolecules. Mechanistic studies on the enantiodifferentiation for the photocyclodimerization of 2-anthracenecarboxylate mediated by bovine serum albumin. J. Org. Chem. 72, 2707–2715 (2007)CrossRefGoogle Scholar
  29. 29.
    T.C.S. Pace, M. Nishijima, T. Wada, Y. Inoue, C. Bohne, Photophysical studies on the supramolecular photochirogenesis for the photocyclodimerization of 2-anthracenecarboxylate within human serum albumin. J. Phys. Chem. B 113, 10445–10453 (2009)CrossRefGoogle Scholar
  30. 30.
    K. Bando, T. Zako, M. Sakono, M. Maeda, T. Wada, M. Nishijima, G. Fukuhara, C. Yang, T. Mori, T.C.S. Pace, C. Bohne, Y. Inoue, Bio-supramolecular photochirogenesis with molecular chaperone: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin. Photochem. Photobiol. Sci. 9, 655–660 (2010)CrossRefGoogle Scholar
  31. 31.
    T. Peters Jr, All About Albumin: Biochemistry, Genetics, and Medical Applications (Academic Press, San Diego, 1996)Google Scholar
  32. 32.
    T. Peters Jr, Adv. Protein Chem. 37, 161–245 (1985)CrossRefGoogle Scholar
  33. 33.
    D.C. Carter, J.X. Ho, Adv. Protein Chem. 45, 153–203 (1994)CrossRefGoogle Scholar
  34. 34.
    E.L. Gelamo, C.H.T.P. Silva, H. Imasato, M. Tabak, Interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants: spectroscopy and modeling. Biochim. Biophys. Acta 1594, 84–99 (2002)CrossRefGoogle Scholar
  35. 35.
    L.F.M. Ismail, M.S.A. Abdel-Mottaleb, Fluorescence studies of photoactivated acidity of 2,2′-dihydroxy-1,1′-binaphthalene. Int. J. Photoenergy 5, 249–254 (2003)CrossRefGoogle Scholar
  36. 36.
    H. Vorum, B. Honore, Influence of fatty acids on the binding of warfarin and phenprocoumon to human serum albumin with relation to anticoagulant therapy. J. Pharm. Pharmacol. 48, 870–875 (1996)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Masaki Nishijima
    • 1
  • Jae-Won Chang
    • 2
  • Cheng Yang
    • 2
  • Gaku Fukuhara
    • 2
  • Tadashi Mori
    • 2
  • Yoshihisa Inoue
    • 2
  1. 1.Office for University-Industry CollaborationOsaka UniversitySuitaJapan
  2. 2.Department of Applied ChemistryOsaka UniversitySuitaJapan

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