Artificial urushi: Design, synthesis, and enzymatic curing of new urushiol analogues

Chemistry Letters

Volumn , Issue 10, 2000, Pages 1214-1215

  Kobayashi, Shiro ^a   Ikeda, Ryohei ^b,c   Oyabu, Hiroshi ^d   Tanaka, Hozumi ^c   Uyama, Hiroshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

^c Toyo Ink Mfg Co Ltd   (Japan)

^d Kyoto Municipal Institute of Industrial Technology and Culture   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034354296     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.1214     Document Type: Article

References (14)

1. J. Kumanotani, "Polymer Application of Renewable Resource Materials," ed by C. E. Carraher and L. H. Sperling, Plenum Press, New York (1983), pp. 225-248.
2. D. M. Snyder, J. Chem. Educ., 66, 977 (1989).
3. R. Majima, Ber. Dtsch. Chem. Ges., 42B, 1418 (1909).
4. R. Majima, Ber. Dtsch. Chem. Ges., 55B, 191 (1922).
5. M. Kasamori, M. Sakamoto, K. Awazu, T. Ichikawa, and T. Egashira, "The Polymeric Materials Encyclopedia," ed. by J. C. Salamone, CRC Press, Boca Raton (1996), pp. 3499-3504.
6. R. Oshima, Y. Yamauchi, C. Watanabe, and J. Kumanotani, J. Org. Chem., 50, 2613 (1985).
7. In relevant to this study, there is an article on in vitro enzymatic hardening of urushiols (catechol derivatives with an unsaturated hydrocarbon at 4-position), however, five steps and troublesome procedures were necessary for the synthesis of starting compounds: M. Terada, H. Oyabu, and Y. Aso, J. Jpn. Soc. Colour Mater., 67, 681 (1994).
8. For example, T. Miyakoshi, H. Kobuchi, N. Niimura, and Y. Yoshihiro, Bull. Chem. Soc. Jpn., 64, 2560 (1991).
9. S. Kobayashi, S. Shoda, and H. Uyama, "Catalysis in Precision Polymerization," ed. by S. Kobayashi, John Wiley & Sons, Chichester (1997), Chap. 8.
10. H. Uyama and S. Kobayashi, CHEMTECH, 29(10), 22 (1999).
11. Very recently, we have reported a lipase-catalyzed regioselective acylation of 4-(2-hydroxyethyl)phenol in the side chain with unsaturated fatty acids; T. Tsujimoto, R. Ikeda, H. Uyama, and S. Kobayashi, Chem. Lett., 2000, 1122. Urushiol analogues 1 and 2 were synthesized according to the modified procedure of this literature.
12. 2O), 5.32 (4H, m, -CH=CH-), 6.73-6.91 (3H, m, Ar), 9.06(1H, br, ArOH).
13. H. Oyabu, M. Terada, Y. Aso, and Y. Oda, J. Jpn. Soc. Colour Mater., 68, 729 (1995).
14. S. Kobayashi, High Polymers, Jpn., 48, 124 (1999).