1992 Fiscal Year Final Research Report Summary
Biotransformation with the plant cultured cells-Clarification and development of its enantioselective reactions
| Project/Area Number |
02804042
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
天然物有機化学
|
|---|
| Research Institution | HIROSHIMA UNIVERSITY |
|---|
Principal Investigator |
HIRATA Toshifumi Hiroshima Univ.,Faculty of Science,Professor, 理学部, 教授 (80033926)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
IZUMI Shunsuke Hiroshima Univ.,Faculty of Science, Research Associate, 理学部, 助手 (90203116)
|
|---|
| Project Period (FY) |
1990 – 1992
|
| Keywords | Plant cultured cells / Epoxidase / Reductase / Enantioselectivity / Substrate specificity / Stereospecificity / Biotransformation / Carbon-Carbon double bond |
|---|
| Research Abstract |
Biochemical potentiality of plant cultured cells to transform "foreign substrates" administered exogenously to the plant cell cultures is of considerable interest as a bioreactor. we have examined that the chiral introduction of hydrogen and oxygen atoms into the carbon-carbon double bond of terpene hydrocarbons with the enzyme preparation from the cultured cells of Nicotiana tabacum.
1. Reduction of the C-C double bond of verbenone by a reductase from the cultured cells involves the syn addition of hydrogen atom from the re-re face of the double bond; the hydrogen atoms participating in the reduction at C-2 and C-3 of verbenone originates from the pro-4S hydrogen of NADPH and the medium, respectively.
2. The cultured cells of N. tabacum have the ability to introduce enantioselectively the oxydenated of functions into the carbon-carbon double bond and its allylic position. Isolation and purification of a epoxydase from the cultured cells were performed. The epoxydase was found to discriminate the enantiotopic faces of the carbon-carbon double bonds and enantioselectively oxidize them from its re-re face.
3. The bioconversion of carbone by the immobilized cells of N. tabacum entrapped in Ca alginate beads was investigated. Efficiency of the bioconversion by the immobilized cells was higher than that by the suspension cells. Only the reduction of the carbon-carbon double bond occurs in the medium of pH 7.5 and the reduction of the carbonyl group is prevented.
|
