Highly Diastereaselective Synthesis of Anti-metabolic Peptide Mimics
| Project/Area Number |
18550094
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Synthetic chemistry
|
|---|
| Research Institution | The University of Tokushima |
|---|
Principal Investigator |
NEMOTO Hisao The University of Tokushima, Institute of Health Biosciences, Graduate School, Associate Professor (30208293)
|
|---|
| Project Period (FY) |
2006 – 2007
|
| Project Status |
Completed (Fiscal Year 2007)
|
| Budget Amount *help |
¥4,130,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥330,000)
Fiscal Year 2007: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2006: ¥2,700,000 (Direct Cost: ¥2,700,000)
|
|---|
| Keywords | acyl anion equivalents / acyl cyanide / peptide mimics / palladium-catalyzed reaction / azilidine / π-allvlpalladium complex / anti-metabolic / π-アリルパラジウム中う間体 |
|---|
| 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.
|
Report
(3 results)
Research Products
(28 results)
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Journal Article] Highly Diastereoselective Nucleophilic Addition Reactions of Masked Acyl Cyanide Reagents to tert-Butanesulfinimides2007
Author(s)
Nemoto, Hisao, Moriguti, Hideki, Ma, Rijian, Kawamura, Tomoyuki, Kamiya, Masaki, Shibuya, Masayuki
-
Journal Title
Tetrahedron : Asymm. 18巻・3号
Pages: 383-389
Related Report
-
-
[Journal Article] Synthesis of alpha-Amino Acid Precursors Directly from Aldehydes using Masked Acyl Cyanide Reagents and N,O-Dialkylated Hydroxylamines,.,2006,71,6038-6043:Journal2006
Author(s)
Nemoto, Hisao, Ma, Rijian, Kawamura, Tomoyuki, Kamiya, Masaki, Shibuya, Masayuki
-
Journal Title
J.Org.Chem. 71巻・16号
Pages: 6038-6043
Related Report
-
-
-
-
-
-
-
-
-
-
-
