Isoelectrical Points and Solubility of 6-Aminopenicillanic Acid in Water + 1-Butanol + Butyl Acetate

Su, Min; Wang, Jingkang; Gong, Junbo; Sun, Hua

doi:10.1021/je800403t

Cited by 5 publications

(3 citation statements)

References 3 publications

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“…Since K 2 HPO 4 and K 3 C 6 H 5 O 7 are two basic salts, pH value of the ATPSs based on them is basic. 6-APA has no net charge at its Isoelectric pH (pI = 3.9) 38 , but it is negatively charged in K 2 HPO 4 and K 3 C 6 H 5 O 7 (pH > pI). 6-APA shows more affinity to the top phase in K 2 HPO 4 and K 3 C 6 H 5 O 7 based ATPSs, despite the more hydrophobicity of top phase.…”

Section: Resultsmentioning

confidence: 99%

Separation of phenyl acetic acid and 6-aminopenicillanic acid applying aqueous two-phase systems based on copolymers and salts

Ahsaie

Pazuki

2021

Sci Rep

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Abstract6-Aminopenicillanic acid (6-APA) is used for synthesis of semisynthetic antibiotics. Polymer-salt aqueous two-phase systems (ATPSs) were applied for separation of 6-APA and phenyl acetic acid (PAA), as the products of hydrolyzation reaction of Penicillin G/Penicillin V. The binodal curves of ATPS composed of a copolymer (reverse Pluronic 10R5, Pluronic L35 and PEG-ran-PPG) and a salt (Tri-sodium citrate, tri-potassium citrate, di-potassium phosphate, sodium sulphate and magnesium sulphate) were obtained. The results show that, at a fixed PPG/PEG ratio, block copolymers have larger two-phase region compared with random copolymer. After screening on the partition coefficient of PAA and 6-APA separately, Na2SO4 was selected for studying the effect of the copolymer structure and the composition of salt and copolymer on partitioning, considering higher selectivity of PAA and 6-APA. 10R5-Na2SO4 ATPS was selected as the most appropriate system for separation of 6-APA and PAA. This system was used for separation of mixture of 6-APA and PAA. The results show that selectivity was $$\approx$$ ≈ 53 and smaller in a system, containing a mixture of 6-APA and PAA. This observation can be justified by the interaction between 6-APA and PAA. Molecular interaction between these two molecules were investigated by the Flory–Huggins interaction parameter.

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Section: Resultsmentioning

confidence: 99%

Separation of phenyl acetic acid and 6-aminopenicillanic acid applying aqueous two-phase systems based on copolymers and salts

Ahsaie

Pazuki

2021

Sci Rep

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“…The dissociation constant was measured by the potentiometric titration method. , In a 100 mL cylindrical-jacketed glass vessel furnished with circulating water from a super thermostat water bath (501A, Shanghai Jinghong Laboratory Instrument Co., Ltd., uncertainty: ± 0.1 °C), the inner solution temperature was determined by a mercury-glass thermometer with an uncertainty of ± 0.1 °C and maintained within 25.0 °C ± 0.1 °C. The pH value was measured with a pH meter (FE20/LE438, Mettler-Toledo Instruments Co., Shanghai, uncertainty: 0.01).…”

Section: Methodsmentioning

confidence: 99%

Dissociation Constant and Solubility of (S)-2-Hydroxy-4-phenylbutyric Acid

Tang

Guo

et al. 2013

J. Chem. Eng. Data

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The dissociation constant (pK a) of (S)-2-hydroxy-4-phenylbutyric acid ((S)-HPBA) was determined at 298.2 K by potentiometric titration. (S)-HPBA exhibits a pK a value of 3.81. The solubility of (S)-HPBA in toluene from (288.2 to 343.2) K, in water from (283.2 to 333.2) K, and in ethyl acetate from (278.2 to 313.2) K was measured by the steady-state method. The solubility in all selected solvents increases with the increase of temperature. The solubility of (S)-HPBA in ethyl acetate is much greater than that in water or toluene. Water was found to be a fine alternative to toluene for crystallizing (S)-HPBA and ethyl acetate to be a suitable extraction solvent of (S)-HPBA in the pharmaceutical industry. The experimental solubility data were correlated with the modified Apelblat, Redlich–Kister, Wilson, and universal quasichemical activity coefficient (UNIQUAC) equations, respectively. The Wilson, Redlich–Kister, and modified Apelblat equations show better agreement with the experimental solubility data of (S)-HPBA in toluene, water, and ethyl acetate, respectively. The solubility of (S)-HPBA in aqueous solutions over the pH range from 1.48 to 5.45 at 298.2 K was also determined by the steady-state method, and the corresponding solubility data were separately fitted well with a semi-Henderson–Hasselbalch equation (pH ≤ 4.0) and a linear equation (pH > 4.0).

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“…Since K2HPO4 and K3C6H5O7 are two basic salts, pH value of the ATPSs based on them is greater than one. 6-APA has no net charge at its Isoelectric pH (pI=3.9) [36], but it is negatively charged in K2HPO4 and K3C6H5O7 (pH > pI After the investigation of the effect of salt, Na2SO4 was selected for further study, considering higher partition coefficient for PAA and higher selectivity. 5 mixture points (table 5) Although Pluronic L35 has higher value of HLB and RSN which lead to more hydrophilicity but the hydrophobic molecule (PAA) showed more tendency to the top phase in ATPS based on Pluronic L35 compared with Pluronic 10R5.…”

Section: Distribution Of Biomoleculementioning

confidence: 99%

Separation of Phenyl Acetic Acid and 6-Aminopenicillanic Acid Applying Aqueous Two-Phase Systems Based on Copolymers and Salts

Ahsaie

Pazuki

2020

Preprint

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6-Aminopenicillanic acid (6-APA) is used for synthesis of semisynthetic antibiotics. Polymer-salt aqueous two-phase systems (ATPSs) were applied for separation of 6-aminopenicillanic acid (6-APA) and phenyl acetic acid (PAA), as the products of hydrolyzation reaction of Penicillin G / Penicillin V. The binodal curves of ATPS composed of a copolymer (reverse Pluronic 10R5, Pluronic L35 and PEG-ran-PPG) and a salt (Tri-sodium citrate, tri-potassium citrate, di-potassium phosphate, sodium sulphate and magnesium sulphate) were obtained. The results show that, at a fixed PPG/PEG ratio, block copolymers have larger two-phase region compared with random copolymer. After screening on the partition coefficient of PAA and 6-APA separately, Na2SO4 was selected for studying the effect of the copolymer structure and the composition of salt and copolymer on partitioning, considering higher selectivity of PAA and 6-APA. 10R5-Na2SO4 ATPS was selected as the most appropriate system for separation of 6-APA and PAA. This system was used for separation of mixture of 6-APA and PAA. The results show that selectivity was 53 and smaller in a system, containing a mixture of 6-APA and PAA. This observation can be justified by the interaction between 6-APA and PAA. Molecular interaction between these two molecules were investigated by the Flory-Huggins interaction parameter.

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Isoelectrical Points and Solubility of 6-Aminopenicillanic Acid in Water + 1-Butanol + Butyl Acetate

Cited by 5 publications

References 3 publications

Separation of phenyl acetic acid and 6-aminopenicillanic acid applying aqueous two-phase systems based on copolymers and salts

Separation of phenyl acetic acid and 6-aminopenicillanic acid applying aqueous two-phase systems based on copolymers and salts

Dissociation Constant and Solubility of (S)-2-Hydroxy-4-phenylbutyric Acid

Separation of Phenyl Acetic Acid and 6-Aminopenicillanic Acid Applying Aqueous Two-Phase Systems Based on Copolymers and Salts

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