FIGURE 14.43 Formation of optical pure (+)- and (-)-2a-hydroxy-1,8-cineole (125b and b') from the biotransformation of 1,8-cineole (122) and (+)-limonene (68) by Citrus pathogenic fungi, Penicillium digitatum (Pers.; Fr.) Sacc. KCPYN and Aspergillus niger TBUYN-2. (Modified from Nishimura, H. et al., 1982. Agric. Biol. Chem., 46: 2601-2604; Miyazawa, M. et al., 1995b. Proc. 39th TEAC, pp. 352-353; Noma, Y. and Y. Asakawa, 2007b. Proc. 51st TEAC, pp. 299-301.)
When monoterpenes, such as limonene (68), a-pinene (4), and 3-carene (336), were administered to the cultured cells of Nicotiana tabacum, they were converted to the corresponding epoxides enantio- and stereoselectively. The enzyme (p38) concerning with the epoxidation reaction was purified from the cultured cells by cation exchanged chromatography. The enzyme had not only epoxida-tion activity but also peroxidase activity. Amino acid sequence of p38 showed 89% homology in their 9 amino acid overlap with horseradish peroxidase (Yawata et al., 1998) (Figure 14.44). It was found that limonene and carene were converted to the corresponding epoxides in the presence of hydrogen
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