l-Proline and d-Proline (Chiral Amino Acid Catalysts)

Mandalapu, Dhanaraju

doi:10.1055/s-0034-1380270

“…The product yield increased from 32 % to 36 % upon reducing the temperature from 120 8C to 100 8C, but dropped to 20 % when further decreasing temperature to 80 8C. A volcano-type activity trend was also observed for initial CO 2 pressure (Supporting Information, Table S5, entries [11][12][13][14][15]. At 20 bar, the yield of pyrrole-2-carboxylic acid was 28 %.…”

mentioning

confidence: 75%

“…At present, renewable and cost-effective method for d-proline production is scarce. Since d-proline is a critical precursor for important chemicals such as (À)-secuamamine A and (R)-harmicine, [10] and is a useful catalyst to access many chiral molecules, [11] new protocols for producing d-proline from renewable starting materials is desirable.…”

mentioning

confidence: 99%

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d‐Proline from Furfural

Song

¹

,

Yuen

²

,

Lu

³

et al. 2020

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Production of renewable, high-value N-containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single-step conversion of furfural to pyrrole in 75 % yield as a key N-containing building block, achieved via tandem decarbonylation-amination reactions over tailor-designed Pd@S-1 and H-beta zeolite catalytic system. Pyrrole was further transformed into dl-proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d-proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high-value organonitrogen chemicals through pyrrole as a hub molecule.

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“…e reactions catalyzed by D-Proline (D-Pro) were also investigated, but the catalytic activity of D-Pro might be lower than that of L-Pro (Figure 3). In most cases, L-Pro and D-Pro show similar catalytic performances except for the enantioselectivity of the product [17]. However, in some examples, the yield of the product di ered depending on the proline structure [18].…”

Section: L-pro-catalyzed Reaction In Dmso and Watermentioning

confidence: 94%

Detection of L-Proline-Catalyzed Michael Addition Reaction in Model Biomembrane

Hirose

¹

,

Sugisaki

²

,

Suga

³

et al. 2019

Journal of Chemistry

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A method to detect the L-proline- (L-Pro-) catalyzed Michael addition reaction in model biomembranes has been established, using N-[p(2-benzimidazolyl)phenyl]maleimide and acetone as reactants. The effect of liposome membranes on this reaction was kinetically analyzed using fluorescence spectroscopy. The kinetics of the reaction were different from those of the constituent lipids of the liposomes. Zwitterionic 1,2-dipalmitoyl-sn-glycero-3-phosphocholine liposome, which is in the solid-ordered phase, had a better value of reaction rate, suggesting that the reaction rate constants of this reaction in liposome membrane systems could be regulated by the characteristics of the liposome membrane (i.e., the phase state and surface charge). Based on the results obtained, a plausible model of the L-Pro-catalyzed Michael addition reaction was discussed. The obtained results provide us with an easily detectable method to assess the reactivity of L-Pro in biological systems.

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“…At present, renewable and cost‐effective method for d ‐proline production is scarce. Since d ‐proline is a critical precursor for important chemicals such as (−)‐secu'amamine A and ( R )‐harmicine, [10] and is a useful catalyst to access many chiral molecules, [11] new protocols for producing d ‐proline from renewable starting materials is desirable.…”

Section: Figurementioning

confidence: 99%

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d‐Proline from Furfural

Song

¹

,

Yuen

²

,

Lu

³

et al. 2020

View full text Add to dashboard Cite

Production of renewable, high-value N-containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single-step conversion of furfural to pyrrole in 75 % yield as a key N-containing building block, achieved via tandem decarbonylation-amination reactions over tailor-designed Pd@S-1 and H-beta zeolite catalytic system. Pyrrole was further transformed into dl-proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d-proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high-value organonitrogen chemicals through pyrrole as a hub molecule.

show abstract

l-Proline and d-Proline (Chiral Amino Acid Catalysts)

Cited by 12 publications

References 14 publications

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d‐Proline from Furfural

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d‐Proline from Furfural

Detection of L-Proline-Catalyzed Michael Addition Reaction in Model Biomembrane

Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d‐Proline from Furfural

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