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Literature DB >> 29199315

Negishi cross-couplings in the synthesis of amino acids.

Abstract

The Negishi cross-coupling is a powerful C-C bond-forming reaction widely utilised in many areas of organic synthesis. This review details the use of Negishi cross-couplings in the synthesis of unnatural amino acids. The application of this reaction in the preparation of aromatic, heteroaromatic, and, complex amino acid derivatives are reviewed and presented herein.

Mesh：

Substances：
Amino Acids

Year: 2017 PMID： 29199315 DOI： 10.1039/c7ob02682j

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

7 in total

1. Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima.

Authors: Christina E Boville; David K Romney; Patrick J Almhjell; Michaela Sieben; Frances H Arnold
Journal: J Org Chem Date: 2018-04-27 Impact factor: 4.354

Review 2. Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

Authors: William D G Brittain; Christopher R Coxon
Journal: Chemistry Date: 2021-12-02 Impact factor: 5.020

3. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Authors: Steffen Dachwitz; Bjarne Scharkowski; Norbert Sewald
Journal: Chemistry Date: 2021-11-11 Impact factor: 5.020

4. Synthesis of C ₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step.

Authors: Sambasivarao Kotha; Saidulu Todeti
Journal: Beilstein J Org Chem Date: 2019-02-08 Impact factor: 2.883

Negishi cross-couplings in the synthesis of amino acids.

1. Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima.

Review 2. Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

3. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

4. Synthesis of C ₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step.

Review 5. Reprogramming natural proteins using unnatural amino acids.

6. Synthesis of pentafluorosulfanyl (SF₅) containing aromatic amino acids.

Review 7. Synthesis of complex unnatural fluorine-containing amino acids.

Negishi cross-couplings in the synthesis of amino acids.

1. Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima.

Review 2. Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

3. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

4. Synthesis of C 3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step.

Review 5. Reprogramming natural proteins using unnatural amino acids.

6. Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids.

Review 7. Synthesis of complex unnatural fluorine-containing amino acids.

4. Synthesis of C ₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step.

6. Synthesis of pentafluorosulfanyl (SF₅) containing aromatic amino acids.