Enantioselective synthesis of α-amino acids from nitroalkenes

Sabelle, Stéphane; Lucet, Denis; Gall, Thierry Le; Mioskowski, Charles

doi:10.1016/s0040-4039(98)00064-1

Cited by 23 publications

(5 citation statements)

References 23 publications

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“…; Sabelle et al . ). To screen for yeast and develop a practical process for d‐ valine preparation, l ‐valine was used as a sole source of carbon and nitrogen in basal minimal medium to isolate l ‐valine‐degrading micro‐organisms under aerobic condition.…”

Section: Resultsmentioning

confidence: 97%

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Isolation and characterization of l -valine-degrading Candida maltosa DLPU-zpb for d- valine preparation from dl -valine

Zhang

Xin

Chen

et al. 2015

Lett Appl Microbiol

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D-valine is an important raw material for medicines and its demand is increasing year by year. Several approaches for D-valine preparation have been reported, but none of them are likely to provide product at low cost. A newly isolated L-valine-degrading yeast strain Candida maltosa DLPU-zpb was described, which showed asymmetric degrading activity against DL-valine. Thus, a new and practical process for D-valine preparation from DL-valine could be developed. This is the first report of the asymmetric degrading ability of C. maltosa against DL-valine and D-valine preparation from DL-valine.

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Section: Resultsmentioning

confidence: 97%

“…Chiral auxiliaries in stereo asymmetric synthesis are too expensive (Sabelle et al . ). The induced crystallization is not feasible because the production cycle is too long and the optical purity and yield of product are low.…”

Section: Introductionmentioning

confidence: 97%

Isolation and characterization of l -valine-degrading Candida maltosa DLPU-zpb for d- valine preparation from dl -valine

Zhang

Xin

Chen

et al. 2015

Lett Appl Microbiol

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“…145,146 The primary nitro group is converted into the carboxylic acids 309 using NaNO 2 /AcOH in DMSO, followed by reductive cleavage of the oxazolidin-2-one, that leads to the a-amino acids 310 of high enantiomeric purity (Scheme 78).…”

Section: Other Methodsmentioning

confidence: 99%

Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

2004

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“…After oxidation, N-substituted amino acids were obtained in 62-99% yield and with 95-96% enantiomeric excess (Sabelle et al, 1998) (Fig. 60).…”

Section: Oxidation Of Optically Pure 3-nitroalkyl-4-phenyl-2-oxazolidmentioning

confidence: 99%

How to build optically active?-amino acids

Calmès

Daunis

1999

Amino Acids

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Enantioselective synthesis of α-amino acids from nitroalkenes

Cited by 23 publications

References 23 publications

Isolation and characterization of l -valine-degrading Candida maltosa DLPU-zpb for d- valine preparation from dl -valine

Isolation and characterization of l -valine-degrading Candida maltosa DLPU-zpb for d- valine preparation from dl -valine

Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

How to build optically active?-amino acids

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