Enzymatic and Chemoenzymatic Three‐Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines
Abstract: Chemoenzymatic and enzymatic cascade reactions enable the synthesis of complex stereocomplementary 1,3,4‐trisubstituted tetrahydroisoquinolines (THIQs) with three chiral centers in a step‐efficient and selective manner without intermediate purification. The cascade employs inexpensive substrates (3‐hydroxybenzaldehyde and pyruvate), and involves a carboligation step, a subsequent transamination, and finally a Pictet–Spengler reaction with a carbonyl cosubstrate. Appropriate selection of the carboligase and transaminase enzymes enabled the biocatalytic formation of (1R,2S)‐metaraminol. Subsequent cyclization catalyzed either enzymatically by a norcoclaurine synthase or chemically by phosphate resulted in opposite stereoselectivities in the products at the C1 position, thus providing access to both orientations of the THIQ C1 substituent. This highlights the importance of selecting from both chemo‐ and biocatalysts for optimal results.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enzymatic and Chemoenzymatic Three‐Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines ; volume:56 ; number:41 ; year:2017 ; pages:12503-12507 ; extent:5
Angewandte Chemie / International edition. International edition ; 56, Heft 41 (2017), 12503-12507 (gesamt 5)
- Creator
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Erdmann, Vanessa
Lichman, Benjamin R.
Zhao, Jianxiong
Simon, Robert C.
Kroutil, Wolfgang
Ward, John M.
Hailes, Helen C.
Rother, Dörte
- DOI
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10.1002/anie.201705855
- URN
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urn:nbn:de:101:1-2022091305354303102381
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:30 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Erdmann, Vanessa
- Lichman, Benjamin R.
- Zhao, Jianxiong
- Simon, Robert C.
- Kroutil, Wolfgang
- Ward, John M.
- Hailes, Helen C.
- Rother, Dörte
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Chemo-enzymatic cascade reactions
Coupled chemo(enzymatic) reactions in continuous flow
Chemo‐Enzymatic Synthesis of Pyrazines and Pyrroles
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Chemo‐Enzymatic Synthesis of Pyrazines and Pyrroles
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Construction of Chemoenzymatic Linear Cascades for the Synthesis of Chiral Compounds
Engineering of enzymatic redox cascades involving oxygenases
Enzymatic and Chemoenzymatic Three‐Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines
Chemo-enzymatic cascade reactions
Coupled chemo(enzymatic) reactions in continuous flow
Chemo‐Enzymatic Synthesis of Pyrazines and Pyrroles
Coupled chemo(enzymatic) reactions in continuous flow
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Chemo-enzymatic total synthesis of the spirosorbicillinols
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