Industrial Biotransformations

Monooxygenase
Nocardia corallina
● 2-Methyl-1,2-epoxyalkanes are precursors for tertiary alcohols, which can be used in the synthesis
of pharmaceuticals such as prostaglandins:
HO
6) Literature
F
HO
Fig. 1.14.14.1 – 6
C nH 2n+1
Pr2NHnHF or SiF4
MeLi-CuI
O
CnH2n+1
EC 1.14.14.1
● Crosby, J. (1991) Synthesis of optically active compounds: a large scale perspective, Tetrahedron
47, 4789–4846
● Furuhashi, K., Takagi, M. (1984) Optimization of a medium for the production of 1,2-epoxytetradecane
by Nocardia corallina B-276, Appl. Microbiol. Biotechnol. 20, 6–9
● Furuhashi, K., Shintani, M., Takagi, M. (1986) Effects of solvents on the production of epoxides
by Nocardia corallina B-276, Appl. Microbiol. Biotechnol. 23, 218–223
● Furuhashi, K. (1992) Biological routes to optically active epoxides, in: Chirality in Industry
(Collins, A., Sheldrake, G.N., Crosby, J., eds.), pp. 167–186, John Wiley & Sons, London
● Gallagher, S.C., Cammack, R., Dalton, H. (1997) Alkene monooxygenase from Nocardia corallina
B-276 is a member of the class of dinuclear iron proteins capable of stereospecific epoxygenation
reactions, Eur. J. Biochem. 247, 635–641.
● Hirai, T., Fukumasa, M., Nishiyama, I., Yoshizawa, A., Shiratori, N., Yokoyama, A., Yamana,
M. (1991) New ferroelectric crystal having 2-methylalkanoyl group, Ferroelectrics 114, 251–257
● Leak, D., Aikens, P.J., Seyed-Mahmoudian, M. (1992) The microbial production of epoxides,
Tibtech 10, 256–261
● Lilly, M.D. (1994) Advances in biotransformation processes. Eighth P.V. Danckwerts memorial
lecture presented at Glaziers’ Hall, London, U.K. 13 May 1993, Chem. Eng. Sci. 49, 151–159
● Shiratori, N., Yoshizawa, A., Nishiyama, I., Fukumasa, M., Yokoyama, A., Hirai, T., Yamane,
M. (1991) New ferroelectric liquid crystals having 2-fluoro-2-methyl alkanoyloxy group, Mol.
Cryst. Liq. Cryst. 199, 129–140
● Takahashi, O., Umezawa, J., Furuhashi, K., Takagi, M. (1989) Stereocontrol of a tertiary hydroxyl
group via microbial epoxidation. A facile synthesis of prostaglandin ω-chains, Tetrahedron
Lett. 30, 1583–1584
250
C nH 2n+1
Li
NaI
AcOH
I HO
HO