Application of an eremomycin-chiral stationary phase for the separation of dl-methionine using simulated moving bed technology

Zhang, L.; Gedicke, K.; Кузнецов, М. А.; Staroverov, S.M.; Seidel‐Morgenstern, A.

doi:10.1016/j.chroma.2007.04.033

Cited by 24 publications

(11 citation statements)

References 17 publications

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“… Produktivität ( PR ) multipliziert mit der Ausbeute ( RY ) von L ‐ (Kreise) und D ‐Methionin (Dreiecke) als Funktion der injizierten Menge für zwei CSPs (Chirobiotic T, EtOH/H 2 O 40:60 ( v / v ), geschlossene Symbole, und Chirasel E, MeOH/H 2 O (0.1 M NaH 2 PO 4 ) 20:80 ( v / v ), offene Symbole). Vorgegebene Reinheitsanforderung: 99 % 300…”

Section: Chromatographische Enantiomerentrennungunclassified

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2014

Nachr Chem

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Die Verfügbarkeit reiner Enantiomere ist von steigender Bedeutung für die pharmazeutische Industrie sowie auch für die Agrochemie und Biotechnologie. Generell gibt es zwei konkurrierende Ansätze zur Gewinnung von reinen Enantiomeren. Der “chirale” Ansatz basiert auf der Entwicklung einer asymmetrischen Synthese, die selektiv eines der Enantiomere liefert. Der “racemische” Ansatz basiert auf der Trennung eines Gemischs der beiden Enantiomere, wobei hier in den letzten Jahren bemerkenswerte Fortschritte erzielt werden konnten. Dieser Aufsatz fokussiert insbesondere auf enantioselektive Kristallisationsprozesse und präparative Chromatographie, einschließlich hybrider Trennprozesse und der zusätzlichen Integration von Racemisierungsschritten. Zur Illustration dienen mehrere in unserem Arbeitskreis untersuchte Trennungen.

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Section: Chromatographische Enantiomerentrennungunclassified

“…Eine erfolgreiche kontinuierliche Trennung der beiden Methionin‐Enantiomere gelang nach einer sorgfältigen Auslegung des SMB‐Prozesses. Die Gesamtproduktivität des Trennverfahrens wurde zu etwa 0.75 kg kg −1 CSP Tag −1 ermittelt 300…”

Section: Chromatographische Enantiomerentrennungunclassified

Autorenregister / Stichwortregister

2014

Nachr Chem

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“…The application of this new CSP for the preparative enantioseparation of Met using simulated moving bed (SMB) chromatography and 0.1 M NaH 2 PO 4 /MeOH (80/20, v/v) as the mobile phase was presented by Zhang et al [90] ( Table 2). The column to column fluctuations were negligible and long-term stability of the preparative stationary phase was satisfactory according to the results of perturbation experiments performed before and after long-term SMB runs.…”

Section: Application Of Macrocyclic Glycopeptides-based Cspsmentioning

confidence: 99%

Recent advances in the direct and indirect liquid chromatographic enantioseparation of amino acids and related compounds: A review

Ilisz

Aranyi

Pataj

et al. 2012

Journal of Pharmaceutical and Biomedical Analysis

100

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“…However, l ‐methionine was fed as the substrate for SAM production in most cases (Huang et al, ; Kamarthapu, Ragampeta, Rao, & Reddy, ; Zhang, Wang, Su, et al, ; Zhao, Hang, et al, ; Zhao, Shi, et al, ). Only one‐third of the price of l ‐methionine (Ren et al, ; Zhang, Gedicke, Kuznetsov, Staroverov, & Seidel‐Morgenstern, ), dl ‐methionine could be the cost‐saving substrate for industrial production of SAM. However, d ‐methionine transported into the cell through the general amino acid permease (Gap1p) cannot be incorporated for SAM biosynthesis and inhibit the cell growth to a certain extent.…”

Section: Introductionmentioning

confidence: 99%

Efficient production of S‐adenosyl‐l‐methionine from dl‐methionine in metabolic engineered Saccharomyces cerevisiae

Liu

Tang

Shi

et al. 2019

Biotech & Bioengineering

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S-Adenosyl-L-methionine (SAM) is an important small molecule compound widely used in treating various diseases. Although L-methionine is generally used, the low-cost DLmethionine is more suitable as the substrate for industrial production of SAM. However, Dmethionine is inefficient for SAM formation due to the substrate-specificity of SAM synthetase. In order to increase the utilization efficiency of DL-methionine, intracellular conversion of D-methionine to L-methionine was investigated in the type strain Saccharomyces cerevisiae BY4741 and an industrial strain S. cerevisiae HDL. Firstly, via disruption of HPA3 encoding D-amino acid-N-acetyltransferase, D-methionine was accumulated in vivo and no N-acetyl-D-methionine production was observed. Further, codon-optimized D-amino acid oxidase (DAAO) gene from Trigonopsis variabilis (Genbank MK280686) and L-phenylalanine dehydrogenase gene (L-PheDH) from Rhodococcus jostii (Genbank MK280687) were introduced to convert D-methionine to L-methionine, SAM concentration and content was increased by 110% and 72.1% in BY4741 (plasmid borne) and increased by 38.2% and 34.1% in HDL (genome integrated), by feeding 0.5 g/L Dmethionine. Using the recently developed CRISPR tools, the DAAO and L-PheDH expression cassettes were integrated into the HPA3 and SAH1 loci while SAM2 expression was integrated into the SPE2 and GLC3 loci of HDL, and the resultant strain HDL-R2 accumulated 289% and 192% more SAM concentration and content, respectively, by feeding 0.5 g/L DL-methionine. Further, in a 10 L fed-batch fermentation process, 10.3 g/L SAM were accumulated with the SAM content of 242 mg/g dry cell weight by feeding 16 g/L DL-methionine. The strategies used here provided a promising approach to enhance SAM production using low-cost DL-methionine. K E Y W O R D S

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Application of an eremomycin-chiral stationary phase for the separation of dl-methionine using simulated moving bed technology

Cited by 24 publications

References 17 publications

Autorenregister / Stichwortregister

Autorenregister / Stichwortregister

Recent advances in the direct and indirect liquid chromatographic enantioseparation of amino acids and related compounds: A review

Efficient production of S‐adenosyl‐l‐methionine from dl‐methionine in metabolic engineered Saccharomyces cerevisiae

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