Solubility of l-serine, l-threonine and l-isoleucine in aqueous aliphatic alcohol solutions

Ferreira, Luísa A.; Pinho, Simão P.; Macedo, Eugénia A.

doi:10.1016/j.fluid.2008.05.008

Cited by 31 publications

(31 citation statements)

References 33 publications

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“…Ser tends to form a hydrate in aqueous solutions (Figure S2 in ESI); PC-SAFT modelling was not applied for Ser. For Thr the PC-SAFT modelled solubility are in good agreement with the experimental data from this work and from literature 7 .…”

Section: Solubility Of Amino Acids In Aqueous-2-propanol Solutions At Saturated Phsupporting

confidence: 87%

“…Several aqueous solubility data in can be found based on different aliphatic alcohols (methanol, ethanol, 1-propanol and 2-propanol) at one or different temperatures. Ferreira et al measured the solubility of glycine and DL-alanine 6 and L-serine, L-threonine and L-isoleucine 7 . Orealla and Kirwan 8 measured solubility of glycine, L-alanine, L-isoleucine, L-phenylalanine and L-asparagine monohydrate.…”

Section: Introductionmentioning

confidence: 99%

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Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Tam

Franke

Volpert

et al. 2021

Phys. Chem. Chem. Phys.

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Section: Solubility Of Amino Acids In Aqueous-2-propanol Solutions At Saturated Phsupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Tam

Franke

Volpert

et al. 2021

Phys. Chem. Chem. Phys.

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“…However, just a few liquid-liquid equilibrium data have been reported in the literature [12][13][14][15]. Solid-liquid equilibrium data have been also reported [16].…”

Section: Introductionmentioning

confidence: 99%

Liquid–Liquid Equilibria of Water + 1-Butanol + Amino Acid (Glycine or dl-Alanine or l-Leucine) at 313.15 K

2014

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Amino acids play an important role both in animal metabolism and in industrial processes. Since they are rarely found in nature in a free form, they must be obtained by biosynthesis or protein hydrolysis, often resulting in aqueous mixtures containing various solutes including several types of amino acids. As a consequence, the cost of the separation processes and concentration of amino acids can be as high as 90 % of their total manufacturing cost. In this way, the design of such processes requires knowledge of the partitioning behavior in two-phase systems and thermodynamic models should support this optimization procedure. However, both the complexity of biomolecules, due to their multiple functional groups, and the crucial role of water make the standard available thermodynamic models unattractive for the computation of phase behavior. Therefore, new thermodynamic models for the description of the phase behavior of systems containing biomolecules are required. In this work, liquid-liquid equilibrium data of the ternary systems 1-butanol ? water ? amino acid (glycine, DL-alanine or L-leucine) were measured at 313.15 K. The experimental results were correlated and interaction parameters were estimated for the modified-NRTL, UNIFAC and UNIFAC-Campinas models. The modified-NRTL model was able to describe the data better than the UNIFAC and UNIFACCampinas models.

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“…L-Ile is the most hydrophobic amino acid. Its solubility is 32.5 g·L −1 (247.75 mM) in aqueous solution at 25 °C [ 37 ]. To further improve transformation efficiency of cell-free enzymatic system for 4-HIL synthesis, we explored methods of feeding l -Ile in a 500 mL bioreactor ( Figure 6 ).…”

Section: Resultsmentioning

confidence: 99%

2-Ketoglutarate-Generated In Vitro Enzymatic Biosystem Facilitates Fe(II)/2-Ketoglutarate-Dependent Dioxygenase-Mediated C–H Bond Oxidation for (2s,3r,4s)-4-Hydroxyisoleucine Synthesis

Jing

Liu

Nie

et al. 2020

IJMS

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Fe(II)/2-ketoglutarate-dependent dioxygenase (Fe(II)/2-KG DO)-mediated hydroxylation is a critical type of C–H bond functionalization for synthesizing hydroxy amino acids used as pharmaceutical raw materials and precursors. However, DO activity requires 2-ketoglutarate (2-KG), lack of which reduces the efficiency of Fe(II)/2-KG DO-mediated hydroxylation. Here, we conducted multi-enzymatic syntheses of hydroxy amino acids. Using (2s,3r,4s)-4-hydroxyisoleucine (4-HIL) as a model product, we coupled regio- and stereo-selective hydroxylation of l-Ile by the dioxygenase IDO with 2-KG generation from readily available l-Glu by l-glutamate oxidase (LGOX) and catalase (CAT). In the one-pot system, H2O2 significantly inhibited IDO activity and elevated Fe2+ concentrations of severely repressed LGOX. A sequential cascade reaction was preferable to a single-step process as CAT in the former system hydrolyzed H2O2. We obtained 465 mM 4-HIL at 93% yield in the two-step system. Moreover, this process facilitated C–H hydroxylation of several hydrophobic aliphatic amino acids to produce hydroxy amino acids, and C–H sulfoxidation of sulfur-containing l-amino acids to yield l-amino acid sulfoxides. Thus, we constructed an efficient cascade reaction to produce 4-HIL by providing prerequisite 2-KG from cheap and plentiful l-Glu and developed a strategy for creating enzymatic systems catalyzing 2-KG-dependent reactions in sustainable bioprocesses that synthesize other functional compounds.

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Solubility of l-serine, l-threonine and l-isoleucine in aqueous aliphatic alcohol solutions

Cited by 31 publications

References 33 publications

Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Liquid–Liquid Equilibria of Water + 1-Butanol + Amino Acid (Glycine or dl-Alanine or l-Leucine) at 313.15 K

2-Ketoglutarate-Generated In Vitro Enzymatic Biosystem Facilitates Fe(II)/2-Ketoglutarate-Dependent Dioxygenase-Mediated C–H Bond Oxidation for (2s,3r,4s)-4-Hydroxyisoleucine Synthesis

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