Scale-Up of a Chemo-Biocatalytic Route to (2R,4R)- and (2S,4S)-Monatin
Monatin, a natural sweetener, refers to a collection of four isomers of 2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentanedioic acid. A chemo-biocatalytic approach to kilogram quantities of enantiopure 2S,4S-monatin and 2R,4R-monatin from indole is described. Key steps in the process include a (2 +...
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| Veröffentlicht in: | Organic process research & development 2011-01, Vol.15 (1), p.249-257 |
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| container_title | Organic process research & development |
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| creator | Rousseau, Amanda L Buddoo, Subash R Gordon, Gregory E. R Beemadu, Sharon Kupi, B. Godfrey Lepuru, M. Jerry Maumela, Munaka C Parsoo, Arvesh Sibiya, Duncan M Brady, Dean |
| description | Monatin, a natural sweetener, refers to a collection of four isomers of 2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentanedioic acid. A chemo-biocatalytic approach to kilogram quantities of enantiopure 2S,4S-monatin and 2R,4R-monatin from indole is described. Key steps in the process include a (2 + 3) cycloaddition reaction followed by nickel-catalysed reduction to construct the monatin backbone, and a highly selective enzyme resolution of the 2S,4S- and 2R,4R-monatin diastereomeric pair to afford each enantiomer in 99% ee. |
| doi_str_mv | 10.1021/op1001947 |
| format | Article |
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| title | Scale-Up of a Chemo-Biocatalytic Route to (2R,4R)- and (2S,4S)-Monatin |
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