Skip to main content
SpringerLink
Log in

Bio-supramolecular photochirogenesis with molecular chaperone: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Photocyclodimerization of 2-anthracenecarboxylate mediated by molecular chaperone protein was performed for the first time to afford chiral syn-head-to-tail and anti-head-to-head dimers (2 and 3) in 10% and 16% enantiomeric excess, respectively, with enhanced yields of sterically and electrostatically less-favored head-to-head dimers (3 and 4).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. H. Rau, Asymmetric photochemistry in solution, Chem. Rev., 1983, 83, 535.

    Article  CAS  Google Scholar 

  2. Y. Inoue, Asymmetric photochemical reactions in solution, Chem. Rev., 1992, 92, 741.

    Article  CAS  Google Scholar 

  3. J. P. Pete, Asymmetric photoreactions of conjugated enones and esters, Adv. Photochem., 1996, 21, 135.

    CAS  Google Scholar 

  4. S. R. L. Everitt and Y. Inoue, in Molecular and Supramolecular Photochemistry, ed. V. Ramamurthy and K. S. Schanze, Marcel Dekker, New York, 1999, vol. 3, p. 71.

  5. A. G. Griesbeck and U. J. Meierhenrich, Asymmetric photochemistry and photochirogenesis, Angew. Chem., Int. Ed., 2002, 41, 3147.

    Article  Google Scholar 

  6. B. Grosch, C. N. Orlebar, E. Herdtweck, W. Massa and T. Bach, Highly enantioselective Diels–Alder reaction of a photochemically generated o-quinodimethane with olefins, Angew. Chem., Int. Ed., 2003, 42, 3693.

    Article  CAS  Google Scholar 

  7. Y. Inoue and V. Ramamurthy, Chiral photochemistry, Marcel Dekker, New York, 2004.

    Book  Google Scholar 

  8. Y. Inoue, Light on chirality, Nature, 2005, 436, 1099.

    Article  CAS  PubMed  Google Scholar 

  9. C. Muller and T. Bach, Chirality control in photochemical reactions: Enantioselective formation of complex photoproducts in solution, Aust. J. Chem., 2008, 61, 557.

    Article  CAS  Google Scholar 

  10. N. Hoffmann, Photochemical reactions as key steps in organic synthesis, Chem. Rev., 2008, 108, 1052.

    Article  CAS  PubMed  Google Scholar 

  11. V. P. Rao and N. J. Turro, Asymmetric induction in benzoin by photolysis of benzaldehyde adsorbed in cyclodextrin cavities, Tetrahedron Lett., 1989, 30, 4641.

    Article  CAS  Google Scholar 

  12. S. Koodanjeri, A. Joy and V. Ramamurthy, Asymmetric induction with cyclodextrins: photocyclization of tropolone alkyl ethers, Tetrahedron, 2000, 56, 7003.

    Article  CAS  Google Scholar 

  13. K. Vízvárdi, K. Desmet, I. Luyten, P. Sandra, G. Hoornaert and E. V. Eycken, Asymmetric induction in intramolecular meta photocycloaddition: cyclodextrin-mediated solid-phase photochemistry of various phenoxyalkenes, Org. Lett., 2001, 3, 1173.

    Article  PubMed  CAS  Google Scholar 

  14. S. Koodanjeri and V. Ramamurthy, Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives, Tetrahedron Lett., 2002, 43, 9229.

    Article  CAS  Google Scholar 

  15. J. Shailaja, S. Karthikeyan and V. Ramamurthy, Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones, Tetrahedron Lett., 2002, 43, 9335.

    Article  CAS  Google Scholar 

  16. A. Nakamura and Y. Inoue, Supramolecular catalysis of the enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate by γ-cyclodextrin, J. Am. Chem. Soc., 2003, 125, 966.

    Article  CAS  PubMed  Google Scholar 

  17. H. Ikeda, T. Nihei and A. Ueno, Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispyridinio-appended γ-cyclodextrin, J. Org. Chem., 2005, 70, 1237.

    Article  CAS  PubMed  Google Scholar 

  18. A. Furutani, K. Katayama, Y. Ueshima, M. Ogura, Y. Tobe, H. Kurosawa, K. Tsutsumi, T. Morimoto and K. Kakiuchi, Asymmetric [2+2] photocycloaddition of cycloalkenone-cyclodextrin complexes to ethylene, Chirality, 2006, 18, 217.

    Article  CAS  PubMed  Google Scholar 

  19. Y. Inoue, F. Dong, K. Yamamoto, L.-H. Tong, H. Tsuneishi, T. Hakushi and A. Tai, Inclusion-enhanced optical yield and E/Z ratio in enantiodifferentiating photoisomerization of cyclooctene included and sensitized by β-cyclodextrin monobenzoate, J. Am. Chem. Soc., 1995, 117, 11033.

    Article  CAS  Google Scholar 

  20. Y. Inoue, T. Wada, N. Sugahara, K. Yamamoto, K. Kimura, L.-H. Tong, X.-M. Gao, Z.-J. Hou and Y. Liu, Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins, J. Org. Chem., 2000, 65, 8041.

    Article  CAS  PubMed  Google Scholar 

  21. Y. Gao, M. Inoue, T. Wada and Y. Inoue, Supramolecular photochirogenesis. 3. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-mono(o-methoxybenzoyl)-β-cyclodextrin, J. Inclusion Phenom. Macrocyclic Chem., 2004, 50, 111.

    Article  CAS  Google Scholar 

  22. R. Lu, C. Yang, Y. Cao, L. Tong, W. Jiao, T. Wada, Z. Wang, T. Mori and Y. Inoue, Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified β-cyclodextrins: critical control by a host structure, J. Org. Chem., 2008, 73, 7695.

    Article  CAS  PubMed  Google Scholar 

  23. A. Joy, V. Ramamurthy, J. R. Scheffer and D. R. Corbin, Enantioselective photoelectrocyclization within zeolites: tropolone methyl ether in chirally modified NaY, Chem. Commun., 1998, 1379.

    Google Scholar 

  24. A. Joy, R. Scheffer and V. Ramamurthy, Chirally modified zeolites as reaction media: photochemistry of an achiral tropolone ether, Org. Lett., 2000, 2, 119.

    Article  CAS  PubMed  Google Scholar 

  25. N. J. Turro, From boiling stones to smart crystals: supramolecular and magnetic isotope control of radical-radical reactions in zeolites, Acc. Chem. Res., 2000, 33, 637.

    Article  CAS  PubMed  Google Scholar 

  26. T. Wada, M. Shikimi, Y. Inoue, G. Lem and N. J. Turro, First photosensitized enantiodifferentiating isomerization by optically active sensitizer immobilized in zeolite supercages, Chem. Commun., 2001, 1864.

    Google Scholar 

  27. K. C. W. Chong, J. Sivaguru, T. Shichi, Y. Yoshimi, V. Ramamurthy and J. R. Scheffer, Use of chirally modified zeolites and crystals in photochemical asymmetric synthesis, J. Am. Chem. Soc., 2002, 124, 2858.

    Article  CAS  PubMed  Google Scholar 

  28. J. Sivaguru, A. Natarajan, L. S. Kaanumalle, J. Shailaja, S. Uppili, A. Joy and V. Ramamurthy, Asymmetric photoreactions within zeolites: role of confinement and alkali metal ions, Acc. Chem. Res., 2003, 36, 509.

    Article  CAS  PubMed  Google Scholar 

  29. J. Sivaguru, T. Poon, R. Franz, S. Jockusch, W. Adam and N. J. Turro, Stereocontrol within confined spaces: enantioselective photooxidation of enecarbamates inside zeolites supercages, J. Am. Chem. Soc., 2004, 126, 10816.

    Article  CAS  PubMed  Google Scholar 

  30. J. Sivaguru, H. Saito, M. R. Solomon, L. S. Kaanumalle, T. Poon, S. Jockusch, W. Adam, V. Ramamurthy, Y. Inoue and N. J. Turro, Control of chirality by cations in confined spaces: photooxidation of enecarbamates inside zeolite supercages, Photochem. Photobiol., 2006, 82, 123.

    Article  CAS  PubMed  Google Scholar 

  31. K. Sivasubramanian, L. S. Kaanumalle, S. Uppili and V. Ramamurthy, Value of zeolites in asymmetric induction during photocyclization of pyridones, cyclohexadienones and naphthalenones, Org. Biomol. Chem., 2007, 5, 1569.

    Article  CAS  PubMed  Google Scholar 

  32. T. Wada, N. Sugahara, M. Kawano and Y. Inoue, First asymmetric photochemistry with nucleosides and DNA: Enantiodifferentiating Z-E photoisomerization of cyclooctene, Chem. Lett., 2000, 1174.

    Google Scholar 

  33. T. Bach, H. Bergmann, B. Grosch and 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., 2002, 124, 7982.

    Article  CAS  PubMed  Google Scholar 

  34. D. F. Cauble, V. Lynch and M. J. Krische, Studies on the enantioselective catalysis of photochemically promoted transformations: “sensitizing receptors” as chiral catalysts, J. Org. Chem., 2003, 68, 15.

    Article  CAS  PubMed  Google Scholar 

  35. A. Bauer, F. Weskamper, S. Grimme and T. Bach, Catalytic enantioselective reactions driven by photoinduced electron transfer, Nature, 2005, 436, 1139.

    Article  CAS  PubMed  Google Scholar 

  36. J. Mizoguchi, Y. Kawanami, T. Wada, K. Kodama, K. Anzai, T. Yanagi and Y. Inoue, Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4-pyrrolidinyl)benzamide template, Org. Lett., 2006, 8, 6051.

    Article  CAS  PubMed  Google Scholar 

  37. Y. Kawanami, T. C. S. Pace, J. Mizoguchi, T. Yanagi, M. Nishijima, T. Mori, T. Wada, C. Bohne and Y. Inoue, Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates, J. Org. Chem., 2009, 74, 7908.

    Article  CAS  PubMed  Google Scholar 

  38. Y. Gao, T. Wada, K. Yang and Y. Inoue, Supramolecular photochirogenesis in sensitizing chiral nanopore: Enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by POST-1, Chirality, 2005, 17, S19.

    Article  CAS  PubMed  Google Scholar 

  39. T. Wada, M. Nishijima, T. Fujisawa, N. Sugahara, T. Mori, A. Nakamura and Y. Inoue, Bovine serum albumin-mediated enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate, J. Am. Chem. Soc., 2003, 125, 7492.

    Article  CAS  PubMed  Google Scholar 

  40. M. Nishijima, T. Wada, T. Mori, T. C. S. Pace, C. Bohne and Y. Inoue, Highly enantiomeric supramolecular [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by human serum albumin, J. Am. Chem. Soc., 2007, 129, 3478.

    Article  CAS  PubMed  Google Scholar 

  41. M. Nishijima, T. C. S. Pace, A. Nakamura, T. Mori, T. Wada, C. Bohne and Y. Inoue, Supramolecular photochirogenesis with biomolecules. Mechanistic studies on the enantiondifferentiation for the photocyclodimerization of 2-anthracenecarboxylate mediated by bovine serum albumin, J. Org. Chem., 2007, 72, 2707.

    Article  CAS  PubMed  Google Scholar 

  42. T. C. S. Pace, M. Nishijima, T. Wada, Y. Inoue and C. Bohne, Photophysical studies on the supramolecular photochirogenesis for the photocyclodimerization of 2-anthracenecarboxylate within human serum albumin, J. Phys. Chem. B, 2009, 113, 10445.

    Article  CAS  PubMed  Google Scholar 

  43. M. Okochi, T. Nomura, T. Zako, T. Arakawa, R. Iizuka, H. Ueda, T. Funatsu, M. Leroux and M. Yohda, Kinetics and binding sites for interaction of the prefoldin with a group II chaperonin, J. Biol. Chem., 2004, 279, 31788.

    Article  CAS  PubMed  Google Scholar 

  44. T. Zako, R. Iizuka, M. Okochi, T. Nomura, T. Ueno, H. Tadakuma, M. Yohda and T. Funatsu, Facilitated release of substrate protein from prefoldin by chaperonin, FEBS Lett., 2005, 579, 3718.

    Article  CAS  PubMed  Google Scholar 

  45. T. Zako, Y. Murase, R. Iizuka, T. Yoshida, T. Kanzaki, N. Ide, M. Maeda, T. Funatsu and M. Yohda, Localization of prefoldin interaction sites in the hyperthermophilic group II chaperonin and correlations between binding rate and protein transfer rate, J. Mol. Biol., 2006, 364, 110.

    Article  CAS  PubMed  Google Scholar 

  46. A. Ohtaki, H. Kida, Y. Miyata, N. Ide, A. Yonezawa, T. Arakawa, R. Iizuka, K. Noguchi, A. Kita, M. Odaka, K. Miki and M. Yohda, Structure and molecular dynamics simulation of archaeal prefoldin: The molecular mechanism for binding and recognition of nonnative substrate proteins, J. Mol. Biol., 2008, 376, 1130.

    Article  CAS  PubMed  Google Scholar 

  47. Y. Kawarabayasi, M. Sawada, H. Horikawa, Y. Haikawa, Y. Hino, S. Yamamoto, M. Sekine, S. Baba, H. Kosugi, A. Hosoyama, Y. Nagai, M. Sakai, K. Ogura, R. Otsuka, H. Nakazawa, M. Takamiya, Y. Ohfuku, T. Funahashi, T. Tanaka, Y. Kudoh, J. Yamazaki, N. Kushida, A. Oguchi, K. Aoki, T. Yoshizawa, Y. Nakamura, F. T. Robb, K. Horikoshi, Y. Masuchi, H. Shizuya and H. Kikuchi, Complete sequence and gene organization of the genome of a hyper-thermophilic archaebacterium, Pyrococcus horikoshii OT3, DNA Res., 1998, 5, 55.

    Article  CAS  PubMed  Google Scholar 

  48. M. Nishijima, T. Wada, K. Nagamori and Y. Inoue, High-sensitivity HPLC quantification of nonfluorescent but photolabile analyte through photoreversion in fluorescence detector, Chem. Lett., 2009, 38, 726.

    Article  CAS  Google Scholar 

  49. R. G. Bennett, P. J. McCartin, Radiationless Deactivation of the Fluorescent State of Substituted Anthracenes, J. Chem. Phys., 1966, 44, 1969.

    Article  CAS  Google Scholar 

  50. R. E. Kellogg, Second Triplet State of Anthracene, J. Chem. Phys., 1965, 43, 411.

    Google Scholar 

  51. E. C. Lim, J. D. Laposa and J. M. H. Yu, Temperature Dependence of Intersystem Crossing in Substituted Anthracenes, J. Mol. Spectrosc., 1966, 19, 412.

    Article  CAS  Google Scholar 

  52. W. R. Ware and B. A. Baldwin, Effect of Temperature on Fluorescence Quantum Yields in Solution, J. Chem. Phys., 1965, 43, 1194.

    Article  CAS  Google Scholar 

  53. C. Bohne, S. R. Kennedy, R. Boch, F. Negri, G. Orlandi, W. Siebrand and J. C. Scaiano, Determination of the Lifetime of the Second Excited Triplet State of Anthracenes, J. Phys. Chem., 1991, 95, 10300.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita, 565-0871, Japan

    Kazuki Bando, Gaku Fukuhara, Cheng Yang, Tadashi Mori & Yoshihisa Inoue

  2. Bioengineering Laboratory, RIKEN, 2-1 Hirosawa, Wako, 351-0198, Japan

    Tamotsu Zako, Masafumi Sakono & Mizuo Maeda

  3. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba, Sendai, 980-8577, Japan

    Takehiko Wada

  4. Center for Advanced Science and Innovation, Osaka University, 2-1 Yamada-oka, Suita, 565-0871, Japan

    Masaki Nishijima

  5. PRESTO, JST, Department of Applied Chemistry, Osaka University, Yamada-oka, Suita, 565-0871, Japan

    Cheng Yang

  6. Department of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada

    Tamara C. S. Pace & Cornelia Bohne

Authors
  1. Kazuki Bando
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tamotsu Zako
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Masafumi Sakono
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mizuo Maeda
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Takehiko Wada
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Masaki Nishijima
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Gaku Fukuhara
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cheng Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Tadashi Mori
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Tamara C. S. Pace
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Cornelia Bohne
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Yoshihisa Inoue
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yoshihisa Inoue.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bando, K., Zako, T., Sakono, M. et al. Bio-supramolecular photochirogenesis with molecular chaperone: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin. Photochem Photobiol Sci 9, 655–660 (2010). https://doi.org/10.1039/b9pp00186g

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b9pp00186g

Search

Navigation