2013 Fiscal Year Final Research Report
Synthesis of beta-heterosubstituted alpha,alpha-disubstituted alpha-amino acid derivatives via enzyme-catalyzed desymmetrization
| Project/Area Number |
24790122
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Drug development chemistry
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| Research Institution | Yasuda Women's University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | β-ヘテロ置換α,α-二置換α-アミノ酸 / リパーゼ触媒 / 非対称化 / 1,3-ジオール / アジリジン / 不斉四級炭素 |
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| Research Abstract |
alpha,alpha-disubstituted beta-amino acids having heteroatoms (oxygen, sulfur or nitrogen) at beta-position are versatile intermediates for synthesis of drugs. In this project, we set up our goal to establish novel and efficient methods to assemble them via lipase-catalyzed enantioselective acetylation (desymmetrization) of symmetric 1,3-propanediol to construct the asymmetric quaternary carbon center.
Ranirestat, an aldose reductase inhibitor for treatment of diabetic complications, has beta-heterosubstituted alpha,alpha-disubstituted alpha-amino acid moiety, and is enantioselectively synthesized (>99% enantiomeric excess). A practical and enantioselective method to access N-carbobenzoxy (S)-alpha-methylserine is also established.
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