1990 Fiscal Year Final Research Report Summary
The Development of Enantioselective Cyanohydrin Synthesis by Artificial Enzyme.
| Project/Area Number |
01850191
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B).
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | The University of Tokyo |
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Principal Investigator |
INOUE Shohei The University of Tokyo, Synthetic Chemistry, Professor, 工学部, 教授 (20010762)
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| Project Period (FY) |
1989 – 1990
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| Keywords | Cyanohydrin / cyclic dipeptide / hydrogen cyanide / ee / cyclo-(S-phenylalanyl-S-histidyl) / mandelonitrile / cyclo-(S-leucyl-S-histidyl) / alpha, beta-unsaturated aldehyde |
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| Research Abstract |
Enantioselective cyanohydrin synthesis catalyzed by cyclic dipeptide by the addition of hydrogen cyanide to aldehydes is carried out. When benzaldehyde was employed as a substrate, optically active mandelonitrile, the corresponding cyanohydrin, was obtained with the enantiomeric excess (ee) of 97%and 97% chemical yield by using the cyclic dipeptide, cyclo- (Phenylalanyl-S-hisidyl) composed of two amino acid residues, Sphenylalanine and S-histidine. The stereochemical outcome of the mandelonitrile was found to be R. On the other hand, the inversion of the stereochemical preference was observed when cyclo- (S-leucyl-S-histidyl) is used as a catalyst to give S-cyanohydrins. Thus, the methodology for the cyanohydrin syntheses of both enantiomers by selecting the amino acid residue in the cyclic dipeptide is established. In addition, hydrocyanation of alpha, beta-unsaturated aldehyde by using cyclo- (S-phenyalanyl-S-histidyl) and cyclo- (S-leucyl-S-histidyl) is carried out to give the corresponding R and S cyanohydrins respectively.
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