Stability of clavulanic acid under variable pH, ionic strength and temperature conditions. A new kinetic approach
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Carvalho et al. found that the optimal conditions for achieving a low CA degradation rate were pH 6.0-7.2 and 20 °C.
“The optimal conditions for achieving a low degradation rate were pH 6.0–7.2 and 20 °C; in contrast, addition of inorganic salts (NaCl, Na2SO4, CaCl2, and MgSO4) increased instability of CA, possibly due to the higher rate of collisions between molecules within the solution [17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
Section 3.1 identifies pH 6.0–7.2 as the best range for CA stability. Section 3.2 describes 20–30 °C as an optimum temperature range, rather than singling out 20 °C, and reports that all four salts increased degradability. It does not attribute that salt effect to more frequent molecular collisions. (LLM, conf=0.84)
Experimental — accuracy not yet measuredThe observed time courses of CA degradation are typical of consecutive equilibrium-irreversible reactions in which the irreversible reaction rate is considerably low compared to the equilibrium reaction (k2 < k1 < k−1).
“The observed time courses of CA degradation are typical of consecutive equilibrium-irreversible reactions in which the reaction rate of the irreversible reaction is considerably low in comparison to the equilibrium reaction (i.e., k2 < k1 < k−1) [17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
Section 3.3 (page unavailable) models the observed CA degradation as a preliminary equilibrium followed by irreversible degradation, supporting the reaction sequence. It reports an equilibrium constant K and an irreversible-degradation constant k_d, but does not establish the claimed ordering k2 < k1 < k−1 or quantify the irreversible rate relative to the forward and reverse equilibrium rates. (LLM, conf=0.88)
Experimental — accuracy not yet measuredAddition of inorganic salts (NaCl, Na2SO4, CaCl2, and MgSO4) increased CA instability.
“The optimal conditions for achieving a low degradation rate were pH 6.0–7.2 and 20 °C; in contrast, addition of inorganic salts (NaCl, Na2SO4, CaCl2, and MgSO4) increased instability of CA, possibly due to the higher rate of collisions between molecules within the solution [17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
CA chemical instability largely depends on pH owing to a carbonyl group linked to the β-lactam ring that is susceptible to acid- or base-catalyzed water attacks.
“CA chemical instability largely depends on the pH-value owing to the presence of a carbonyl group linked to the β-lactam ring, which is susceptible to acid or basic catalyzed water attacks [17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
The significant concentration of intermediate I* after 6 h shifts the equilibrium towards CA, and hence the equilibrium reaction is the rate-limiting step.
“The significant concentration of intermediate I* after 6 shifts the equilibrium towards CA and hence, the equilibrium reaction (Equation (1)) is the rate-limiting step [17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
The calculated Ea for the irreversible process of CA degradation is close to previous reports for CA in fermentation broths.
“The activation energy (Ea) calculated for the irreversible process of degradation was 16.512 kJ/mol which is close to previous reports for CA in fermentation broths [10,17].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [17]
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Research works printed but not linked: 6
- J. Finlay, L. Miller, J.A. Poupard, A review of the antimicrobial activity of clavu- lanate, J. Antimicrob. Chemother. 52 (2003) 18-23.
- P.S. Saudagar, S.A. Survase, R.S. Singhal, Clavulanic acid: A review, Biotechnol. Adv. 26 (2008) 335-351.
- K.S. Pitzer, Electrolyte solutions: introduction and simple examples, in: Ther- modynamics, McGraw-Hill, New York, 1995, pp. 254-274.
- K.J. Laidler (Ed.), Chemical Kinetics, Mc Graw Hill, New York, 1950, pp. 282-294.
- P.A. Bersanetti, M. Barboza, C.O. Hokka, M.L.G.C. Araujo, Estudos cinéticos de hidrólise do ácido clavulânico, in: Proceedings of the 13th XIII National Sym- posium on Fermentations, vol. 6, Teresópolis, Brazil, 2000, pp. 1-39.
- J.E. Bailey, D.F. Ollis, Biochemical Engineering Fundamentals, 2nd edition, Mc Graw-Hill, New York, 1986.
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Ser, H.-L., Law, J. W.-F., Chaiyakunapruk, N., Jacob, S. A., Palanisamy, U. D., Chan, K.-G., Goh, B.-H., & Lee, L.-H. (2016) · Frontiers in Microbiology · doi:10.3389/fmicb.2016.00522 · Cited by 90 · see citing works
Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures
Gómez-Ríos, D., Ramírez-Malule, H., Neubauer, P., Junne, S., & Ríos-Estepa, R. (2019) · Antibiotics · doi:10.3390/antibiotics8010006 · Cited by 17 · see citing works
“The significant concentration of intermediate I* after 6 shifts the equilibrium towards CA and hence, the equilibrium reaction (Equation (1)) is the rate-limiting step [17].”
BackgroundMethodResultInfluentialFeng, T., Zhao, J., Bai, Y.-F., Chu, J., Wang, Y.-H., & Zhuang, Y.-P. (2022) · Preparative Biochemistry & Biotechnology · doi:10.1080/10826068.2021.2009860 · Cited by 3 · see citing works
- Authors
- Santos, V. C., Pereira, J. F. B., Haga, R. B., Rangel-Yagui, C. O., Teixeira, J. A. C., Converti, A., & Pessoa, A.
- Affiliations
- University of Minho (PT)
- Universidade de São Paulo (BR)
- Corresponding author
- Pessoa, Adalberto
- Venue
- Biochemical Engineering Journal
- Publisher
- Elsevier BV
- Published
- 2009-07
- Volume
- 45
- Issue
- 2
- Pages
- 89-93
- ISSN
- 1369-703X (ISSN-L)
- OpenAlex
- W2162538994
- Cited by
- 48
- References
- 0
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 2 · 2023: 1 · 2022: 1 · 2021: 4 · 2020: 1 · 2019: 4 · 2018: 2 · 2017: 2 · 2016: 1 · 2015: 5 · 2014: 5 · 2013: 3 · 2012: 5
- FWCI
- 3.73
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Biochemical Engineering Journal (publishedVersion)
- Scientific Electronic Library Online (São Paulo Research Foundation, Latin American and Caribbean Center on Health Sciences Information, Conselho Nacional de Desenvolvimento Científico e Tecnológico) (publishedVersion)
- CINECA IRIS Institutial Research Information System (University of Genoa) (submittedVersion)
- RepositóriUM (Universidade do Minho) (submittedVersion, other-oa)
- Portuguese National Funding Agency for Science, Research and Technology (RCAAP Project by FCT) (submittedVersion, other-oa)
- Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Topics
- Physical Sciences › Chemical Engineering › Filtration and Separation › Chemical and Physical Properties in Aqueous Solutions
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein purification and stability
- Physical Sciences › Chemistry › Analytical Chemistry › Analytical Methods in Pharmaceuticals
- Keywords
- clavulanic acid, drug stability, pH dependence, ionic strength, temperature dependence, degradation kinetics, beta-lactamase inhibitors, extractive fermentation, downstream processing
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