Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades
| Autor: | Min Huang, Grayson J. Ford, Ashley P. Mattey, Christopher Baldwin, James R. Marshall, William R. Birmingham, Lisa S. Seibt, Nico Kress, Lorna J. Hepworth, Sabine L. Flitsch, Nicholas J. Turner |
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| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
Imine Reductase 010402 general chemistry Galactose Oxidase 01 natural sciences Catalysis chemistry.chemical_compound Piperidines Materials Chemistry Molecule chemistry.chemical_classification Molecular Structure 010405 organic chemistry Metals and Alloys Azepines General Chemistry 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Enzyme chemistry Galactose oxidase Yield (chemistry) Ceramics and Composites Imines Oxidoreductases |
| Zdroj: | Ford, G J, Kress, N, Mattey, A P, Hepworth, L J, Baldwin, C R, Marshall, J R, Seibt, L S, Huang, M, Birmingham, W R, Turner, N J & Flitsch, S L 2020, ' Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades ', Chemical Communications, vol. 56, no. 57, pp. 7949-7952 . https://doi.org/10.1039/d0cc02976a Chemical Communications |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/d0cc02976a |
| Popis: | Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity. |
| Databáze: | OpenAIRE |
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