Asymmetric biomimetic transamination of α-keto amides to peptides
Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemis...
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| Published in | Nature communications Vol. 12; no. 1; pp. 5174 - 9 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
30.08.2021
Nature Publishing Group Nature Portfolio |
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| Online Access | Get full text |
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| Abstract | Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines
1
for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation.
Asymmetric transamination of α-keto amides could provide an efficient strategy to synthesise peptides, but has not been well developed yet. Here, the authors design chiral pyridoxamine catalyst and realize the asymmetric biomimetic transamination of α-keto amides, providing access to various peptides with excellent enantiopurities. |
|---|---|
| AbstractList | Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation.Asymmetric transamination of α-keto amides could provide an efficient strategy to synthesise peptides, but has not been well developed yet. Here, the authors design chiral pyridoxamine catalyst and realize the asymmetric biomimetic transamination of α-keto amides, providing access to various peptides with excellent enantiopurities. Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation. Asymmetric transamination of α-keto amides could provide an efficient strategy to synthesise peptides, but has not been well developed yet. Here, the authors design chiral pyridoxamine catalyst and realize the asymmetric biomimetic transamination of α-keto amides, providing access to various peptides with excellent enantiopurities. Asymmetric transamination of α-keto amides could provide an efficient strategy to synthesise peptides, but has not been well developed yet. Here, the authors design chiral pyridoxamine catalyst and realize the asymmetric biomimetic transamination of α-keto amides, providing access to various peptides with excellent enantiopurities. Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn't need great efforts to make chiral unnatural amino acids before amide bond formation.Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn't need great efforts to make chiral unnatural amino acids before amide bond formation. Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation. |
| ArticleNumber | 5174 |
| Author | Li, Bo Chen, Wen-Wen Zhao, Baoguo Zhang, Liangliang Zhang, Hao Cai, Weiqi Guo, Jianhua Qiao, Xuelong |
| Author_xml | – sequence: 1 givenname: Weiqi surname: Cai fullname: Cai, Weiqi organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 2 givenname: Xuelong surname: Qiao fullname: Qiao, Xuelong organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 3 givenname: Hao surname: Zhang fullname: Zhang, Hao organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 4 givenname: Bo orcidid: 0000-0002-6179-4284 surname: Li fullname: Li, Bo organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 5 givenname: Jianhua surname: Guo fullname: Guo, Jianhua organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 6 givenname: Liangliang surname: Zhang fullname: Zhang, Liangliang organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 7 givenname: Wen-Wen surname: Chen fullname: Chen, Wen-Wen organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University – sequence: 8 givenname: Baoguo orcidid: 0000-0001-7579-6670 surname: Zhao fullname: Zhao, Baoguo email: zhaobg2006@shnu.edu.cn organization: The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University |
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| ContentType | Journal Article |
| Copyright | The Author(s) 2021 The Author(s) 2021. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2021. The Author(s). |
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| DOI | 10.1038/s41467-021-25449-y |
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| Snippet | Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to... Asymmetric transamination of α-keto amides could provide an efficient strategy to synthesise peptides, but has not been well developed yet. Here, the authors... |
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| SubjectTerms | 639/638/77/883 639/638/77/889 Amides Amino acids Asymmetry Biological activity Biomimetic materials Biomimetics Catalysts Enantiomers Humanities and Social Sciences multidisciplinary Peptides Science Science (multidisciplinary) Transaminases |
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| Title | Asymmetric biomimetic transamination of α-keto amides to peptides |
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