2007 Fiscal Year Final Research Report Summary
Highly Diastereaselective Synthesis of Anti-metabolic Peptide Mimics
| Project/Area Number |
18550094
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | The University of Tokushima |
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Principal Investigator |
NEMOTO Hisao The University of Tokushima, Institute of Health Biosciences, Graduate School, Associate Professor (30208293)
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| Project Period (FY) |
2006 – 2007
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| Keywords | acyl anion equivalents / acyl cyanide / peptide mimics / palladium-catalyzed reaction / azilidine / π-allvlpalladium complex / anti-metabolic |
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| Research Abstract |
A palladium-catalyzed highly regio- and stereoselective carbon-carbon bond formation reaction of substituted vinyl azilidine was developed using Masked Acyl Cyanide(MAC)reagent, which was previously invented by us. These reactions gave an important synthetic intermediate toward dipeptide-mimics, whose amide bond was displaced to carbon-carbon double bonds. When the 4-toluenesulfonyl group was used for protecting group of nitrogen, the selective carbon-carbon bond formation reactions were succeeded. However, the relative stereochemistry of the products was not identified. Furthermore, the stereoselectivity was low when trans-azilidine derivative was used. When the 2,4,6-trimethylbenzenesulfonyl group was used in stead of 4-toluenesulfonyl group, chemical yields, regioselectivity, and stereoselectivity of the reaction from both trans-and cis-azilidine were extremely improved (>99%).The relative stereochemistry of the product from both trans- and cis-azilidines were confirmed. This new finding is a useful technique for the synthesis of artificial peptides and promising for post-proteomics.
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