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Literature DB >> 28671344

Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing.

Sarah L Montgomery¹, Juan Mangas-Sanchez¹, Matthew P Thompson¹, Godwin A Aleku¹, Beatriz Dominguez², Nicholas J Turner¹.

Abstract

The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.

Entities: Chemical Species

Keywords: asymmetric amination; biocatalysis; enzyme cascades; reductive aminase; synthetic methods

Year: 2017 PMID： 28671344 DOI： 10.1002/anie.201705848

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

15 in total

Review 1. Borrowing Hydrogen for Organic Synthesis.

Authors: Benjamin G Reed-Berendt; Daniel E Latham; Mubarak B Dambatta; Louis C Morrill
Journal: ACS Cent Sci Date: 2021-03-25 Impact factor: 14.553

2. Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships.

Authors: Sarah L Montgomery; Ahir Pushpanath; Rachel S Heath; James R Marshall; Ulrike Klemstein; James L Galman; David Woodlock; Serena Bisagni; Christopher J Taylor; J Mangas-Sanchez; J I Ramsden; Beatriz Dominguez; Nicholas J Turner
Journal: Sci Adv Date: 2020-05-22 Impact factor: 14.136

3. Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones.

Authors: Valeria Nori; Antonio Arcadi; Armando Carlone; Fabio Marinelli; Marco Chiarini
Journal: Beilstein J Org Chem Date: 2020-05-20 Impact factor: 2.883

4. Sequence-Based In-silico Discovery, Characterisation, and Biocatalytic Application of a Set of Imine Reductases.

Authors: Stefan Velikogne; Verena Resch; Carina Dertnig; Joerg H Schrittwieser; Wolfgang Kroutil
Journal: ChemCatChem Date: 2018-07-17 Impact factor: 5.686

5. N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks.

Authors: Hu Li; Haixin Guo; Yaqiong Su; Yuya Hiraga; Zhen Fang; Emiel J M Hensen; Masaru Watanabe; Richard Lee Smith
Journal: Nat Commun Date: 2019-02-11 Impact factor: 14.919

10. Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines.

Authors: Vasilis Tseliou; Marcelo F Masman; Wesley Böhmer; Tanja Knaus; Francesco G Mutti
Journal: Chembiochem Date: 2019-02-13 Impact factor: 3.164

Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing.

Review 1. Borrowing Hydrogen for Organic Synthesis.

2. Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships.

3. Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones.

4. Sequence-Based In-silico Discovery, Characterisation, and Biocatalytic Application of a Set of Imine Reductases.

5. N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks.

6. RetroBioCat as a computer-aided synthesis planning tool for biocatalytic reactions and cascades.

7. One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation.

8. Mimicking transition metals in borrowing hydrogen from alcohols.

9. Hydrogen-Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases.

10. Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines.