Bacterial Poly(hydroxyalkanoates) as a Source of Chiral Hydroxyalkanoic Acids
Abstract
Polyhydroxyalkanoates (PHA) are polyesters of various hydroxyalkanoates accumulated in numerous bacteria. All of the monomeric units of PHA are enantiomerically pure and in R-configuration. R-Hydroxyalkanoic acids can be widely used as chiral starting materials in fine chemical, pharmaceutical and medical industries. In this study, we established an efficient method for the production of chiral hydroxyalkanoic acid monomers from PHA. Pseudomonas putida cells containing PHA were resuspended in phosphate buffer at different pH. We observed that the optimal initial pH for intracellular PHA degradation and monomer release was at pH 8-11 with pH 11 as the best. At initial pH 11, PHA containing 3-hydroxyoctanoic acid and 3-hydroxyhexanoic acid was degraded with an efficiency of over 90% (w/w) in 9 h, and the yield of the corresponding monomers was also over 90%. Under the same conditions, unsaturated monomers were also effectively produced from PHA containing 3-hydroxy-6-heptenoic acid, 3-hydroxy-8-nonenoic acid, and 3-hydroxy-10-undecenoic acid. The monomers (e.g., 3-hydroxyoctanoic acid) were further isolated using solid phase extraction and purified on reversed phase semipreparative liquid chromatography. We confirmed that the purified 3-hydroxyoctanoic acid monomer has exclusively the R-configuration.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Ren et al. extended the concept to a broader range of PHAs, allowing synthesis of a variety of R-hydroxyalkanoic acids whose structures depend on the parent PHA.
“Ren et al. later extended this concept to a broader range of PHAs, allowing for the synthesis of a variety of R-hydroxyalkanoic acids, the structures of which depend on the parent PHA.490”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [490]
Cites
Synthesis, structure and properties of polyhydroxyalkanoates: biological polyesters
Sudesh, K., Abe, H., & Doi, Y. (2000) · Progress in Polymer Science · doi:10.1016/s0079-6700(00)00035-6 · Cited by 2,261 · see citing works
Diversity of bacterial polyhydroxyalkanoic acids
Steinbüchel, A., & Valentin, H. E. (1995) · FEMS Microbiology Letters · doi:10.1111/j.1574-6968.1995.tb07528.x · Cited by 981 · see citing works
Occurrence, synthesis and medical application of bacterial polyhydroxyalkanoate
Zinn, M., Witholt, B., & Egli, T. W. (2001) · Advanced Drug Delivery Reviews · doi:10.1016/s0169-409x(01)00218-6 · Cited by 803 · see citing works
Self-citationMicrobial Degradation of Polyhydroxyalkanoates
Jendrossek, D., & Handrick, R. (2002) · Annual Review of Microbiology · doi:10.1146/annurev.micro.56.012302.160838 · Cited by 697 · see citing works
Lageveen, R. G., Huisman, G. W., Preusting, H., Ketelaar, P., Eggink, G., & Witholt, B. (1988) · Applied and Environmental Microbiology · doi:10.1128/aem.54.12.2924-2932.1988 · Cited by 694 · see citing works
PHA applications: addressing the price performance issue
Williams, S. F., Martin, D. P., Horowitz, D. M., & Peoples, O. P. (1999) · International Journal of Biological Macromolecules · doi:10.1016/s0141-8130(99)00022-7 · Cited by 473 · see citing works
Enantioselective catalysis in fine chemicals production
Blaser, H. (2003) · Chemical Communications · doi:10.1039/b209968n · Cited by 378 · see citing works
Riis, V., & Mai, W. (1988) · Journal of Chromatography A · doi:10.1016/s0021-9673(01)84535-0 · Cited by 354 · see citing works
Noyori, R., Kitamura, M., & Ohkuma, T. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0307928100 · Cited by 277 · see citing works
Huisman, G. W., Wonink, E., Meima, R., Kazemier, B., Terpstra, P., & Witholt, B. (1991) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)52227-4 · Cited by 275 · see citing works
Witholt, B., & Kessler, B. (1999) · Current Opinion in Biotechnology · doi:10.1016/s0958-1669(99)80049-4 · Cited by 262 · see citing works
Haywood, G. W., Anderson, A. J., Chu, L., et al. (1988) · FEMS Microbiology Letters · doi:10.1111/j.1574-6968.1988.tb02577.x · Cited by 161 · see citing works
Saegusa, H., Shiraki, M., Kanai, C., & Saito, T. (2001) · Journal of Bacteriology · doi:10.1128/jb.183.1.94-100.2001 · Cited by 157 · see citing works
Chiral compounds from bacterial polyesters: Sugars to plastics to fine chemicals
Lee, S. Y., Lee, Y., & Wang, F. (1999) · Biotechnology and Bioengineering · doi:10.1002/(sici)1097-0290(19991105)65:3 · Cited by 129 · see citing works
Novel Biodegradable Aromatic Plastics from a Bacterial Source
Garcı́a, B., Olivera, E. R., Miñambres, B., et al. (1999) · Journal of Biological Chemistry · doi:10.1074/jbc.274.41.29228 · Cited by 126 · see citing works
Dual nutrient limited growth: models, experimental observations, and applications
Zinn, M., Witholt, B., & Egli, T. W. (2004) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2004.03.030 · Cited by 123 · see citing works
Self-citationRuiz, J. A., López, N. I., Fernández, R. O., et al. (2001) · Applied and Environmental Microbiology · doi:10.1128/aem.67.1.225-230.2001 · Cited by 103 · see citing works
Synthesis of poly(3-hydroxyalkanoates) by mutant and recombinant Pseudomonas strains
Huisman, G. W., Wonink, E., de Koning, G., et al. (1992) · Applied Microbiology and Biotechnology · doi:10.1007/bf00169409 · Cited by 92 · see citing works
ROO, G. D., Kellerhals, M. B., Ren, Q., et al. (2002) · Biotechnology and Bioengineering · doi:10.1002/bit.10139 · Cited by 90 · see citing works
Self-citationSolaiman, D. K. Y., Ashby, R. D., & Foglia, T. A. (2003) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-003-1317-4 · Cited by 80 · see citing works
Hartmann, R., Hany, R., Geiger, T., et al. (2004) · Macromolecules · doi:10.1021/ma040035+ · Cited by 75 · see citing works
Self-citationSeebàch, D., Beck, A. K., Breitschuh, R., et al. (2003) · Organic Syntheses · doi:10.1002/0471264180.os071.05 · Cited by 69 · see citing works
Wolf, G., Almeida, J. S., Pinheiro, C., Correia, V., Rodrigues, C., Reis, M. A. M., & Crespo, J. G. (2000) · Biotechnology and Bioengineering · doi:10.1002/1097-0290(20010205)72:3 · Cited by 69 · see citing works
Hazenberg, W., & Witholt, B. (1997) · Applied Microbiology and Biotechnology · doi:10.1007/s002530051100 · Cited by 58 · see citing works
Biosynthesis of polyesters in bacteria and recombinant organisms
Steinbüchel, A., Füchtenbusch, B., Gorenflo, V. M., et al. (1998) · Polymer Degradation and Stability · doi:10.1016/s0141-3910(97)00173-0 · Cited by 47 · see citing works
Utaka, M., Watabu, H., Higashi, H., et al. (1990) · The Journal of Organic Chemistry · doi:10.1021/jo00299a041 · Cited by 45 · see citing works
Synthesis and Breakdown of Poly- -Hydroxybutyric Acid by Bacteria
Hayward, A. C., Forsyth, W. G. C., & ROBERTS, J. B. (1959) · Journal of General Microbiology · doi:10.1099/00221287-20-3-510 · Cited by 36 · see citing works
(1993) · Organic Syntheses · doi:10.15227/orgsyn.071.0039 · Cited by 35 · see citing works
Zhang, J., Duetz, W. A., Witholt, B., et al. (2004) · Chemical Communications · doi:10.1039/b407004f · Cited by 24 · see citing works
Foster, L. J. R., Lenz, R. W., & Fuller, R. C. (1999) · International Journal of Biological Macromolecules · doi:10.1016/s0141-8130(99)00081-1 · Cited by 23 · see citing works
Xenon probe for detecting the microporous structure of nanosized HZSM-5 zeolite
Zhang, W., Han, X., Liu, X., et al. (2001) · Chemical Communications · doi:10.1039/b009015h · Cited by 18 · see citing works
Activities of Extracellular and Intracellular Depolymerases of Polyhydroxyalkanoates
Foster, L. J. R., Fuller, R. C., & Lenz, R. W. (1996) · ACS symposium series · doi:10.1021/bk-1996-0627.ch007 · Cited by 6 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Plastics derived from biological sources: present and future: a technical and environmental review
Chen, G.-Q., & Patel, M. K. (2012) · Chemical Reviews · doi:10.1021/cr200162d · Cited by 997 · see citing works
Catalysis as an Enabling Science for Sustainable Polymers
Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00329 · Cited by 936 · see citing works
Enatiomerically pure hydroxycarboxylic acids: current approaches and future perspectives
Ren, Q., Ruth, K., Thöny-Meyer, L., & Zinn, M. (2010) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-010-2530-6 · Cited by 113 · see citing works
Self-citation
- Authors
- Ren, Q., Grubelnik, A., Hoerler, M., Ruth, K., Hartmann, R., Felber, H., & Zinn, M.
- Affiliations
- ETH Zurich (CH)
- Corresponding author
- Ren, Qun
- Venue
- Biomacromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-05-26
- Volume
- 6
- Issue
- 4
- Pages
- 2290-2298
- ISSN
- 1525-7797 (ISSN-L)
- 1526-4602
- OpenAlex
- W2031434733
- Cited by
- 106
- References
- 32
- Citations by year
- 2025: 4 · 2024: 2 · 2023: 3 · 2022: 5 · 2021: 4 · 2020: 1 · 2019: 6 · 2018: 5 · 2017: 4 · 2016: 4 · 2015: 5 · 2014: 8 · 2013: 5 · 2012: 7
- FWCI
- 2.55
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biomacromolecules (publishedVersion)
- PubMed (publishedVersion)
- DORA Eawag (Swiss Federal Institute of Aquatic Science and Technology (Eawag)) (submittedVersion)
- DORA Empa (Swiss Federal Laboratories for Materials Science and Technology (Empa)) (submittedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Enzyme Catalysis and Immobilization
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Keywords
- polyhydroxyalkanoates, monomer release, pH effect, Pseudomonas putida, unsaturated monomers, enantiomeric purity, solid-phase extraction
- MeSH terms
- Acids, Alkanes, Hydrogen-Ion Concentration, Kinetics, Stereoisomerism, Water, Reproducibility of Results, Pseudomonas putida
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
