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Chiral amine synthesis using ω-transaminases: an amine donor that displaces equilibria and enables high-throughput screening.

Green AP, Turner NJ, O'Reilly E - Angew. Chem. Int. Ed. Engl. (2014)

Bottom Line: The widespread application of ω-transaminases as biocatalysts for chiral amine synthesis has been hampered by fundamental challenges, including unfavorable equilibrium positions and product inhibition.This operationally simple method is compatible with the most widely used (R)- and (S)-selective ω-TAs and is particularly suitable for the conversion of substrates with unfavorable equilibrium positions (e.g., 1-indanone).Significantly, spontaneous polymerization of the isoindole by-product generates colored derivatives, providing a high-throughput screening platform to identify desired ω-TA activity.

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Affiliation: School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN (UK). anthony.green@manchester.ac.uk.

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Conversion of 2 (100 mm) into (S)-3 using diamine donor 1 (1.1 equiv). [a] Yield of isolated product. HEPES=4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid.
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fig03: Conversion of 2 (100 mm) into (S)-3 using diamine donor 1 (1.1 equiv). [a] Yield of isolated product. HEPES=4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid.


Chiral amine synthesis using ω-transaminases: an amine donor that displaces equilibria and enables high-throughput screening.

Green AP, Turner NJ, O'Reilly E - Angew. Chem. Int. Ed. Engl. (2014)

Conversion of 2 (100 mm) into (S)-3 using diamine donor 1 (1.1 equiv). [a] Yield of isolated product. HEPES=4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4497610&req=5

fig03: Conversion of 2 (100 mm) into (S)-3 using diamine donor 1 (1.1 equiv). [a] Yield of isolated product. HEPES=4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid.
Bottom Line: The widespread application of ω-transaminases as biocatalysts for chiral amine synthesis has been hampered by fundamental challenges, including unfavorable equilibrium positions and product inhibition.This operationally simple method is compatible with the most widely used (R)- and (S)-selective ω-TAs and is particularly suitable for the conversion of substrates with unfavorable equilibrium positions (e.g., 1-indanone).Significantly, spontaneous polymerization of the isoindole by-product generates colored derivatives, providing a high-throughput screening platform to identify desired ω-TA activity.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN (UK). anthony.green@manchester.ac.uk.

Show MeSH
Related in: MedlinePlus