Production of 3-Hydroxypropanoic Acid From Glycerol by Metabolically Engineered Bacteria

Jers, Carsten; Kalantari, Aida; Garg, Abhroop; Mijaković, Ivan

doi:10.3389/fbioe.2019.00124

Cited by 37 publications

(30 citation statements)

References 90 publications

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“…Since known components of the crystal mother liquor could not account for the electron density, we further considered possible contaminants that the density could represent. 3-hydroxypropionic acid is a known precursor and contaminant of the polyacrylate used for Av3MDO crystallization, which we confirmed by mass spectrometry, and was considered the most likely source of the electron density feature (73,74). Additionally, 3HPA is a close analog of the 3MPA substrate of Av3MDO.…”

Section: Structure Refinement and Analysissupporting

confidence: 63%

Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

York

Sardar

Khadka

et al. 2021

Journal of Biological Chemistry

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Thiol dioxygenases are a subset of nonheme iron oxygenases that catalyze the formation of sulfinic acids from sulfhydryl-containing substrates and dioxygen. Among this class, cysteine dioxygenases (CDOs) and 3-mercaptopropionic acid dioxygenases (3MDOs) are the best characterized, and the mode of substrate binding for CDOs is well understood. However, the manner in which 3-mercaptopropionic acid (3MPA) coordinates to the nonheme iron site in 3MDO remains a matter of debate. A model for bidentate 3MPA coordination at the 3MDO Fe-site has been proposed on the basis of computational docking, whereas steady-state kinetics and EPR spectroscopic measurements suggest a thiolate-only coordination of the substrate. To address this gap in knowledge, we determined the structure of Azobacter vinelandii 3MDO ( Av 3MDO) in complex with the substrate analog and competitive inhibitor, 3-hydroxypropionic acid (3HPA). The structure together with DFT computational modeling demonstrates that 3HPA and 3MPA associate with iron as chelate complexes with the substrate-carboxylate group forming an additional interaction with Arg168 and the thiol bound at the same position as in CDO. A chloride ligand was bound to iron in the coordination site assigned as the O 2 -binding site. Supporting HYSCORE spectroscopic experiments were performed on the (3MPA/NO)-bound Av 3MDO iron nitrosyl ( S = 3/2) site. In combination with spectroscopic simulations and optimized DFT models, this work provides an experimentally verified model of the Av 3MDO enzyme–substrate complex, effectively resolving a debate in the literature regarding the preferred substrate-binding denticity. These results elegantly explain the observed 3MDO substrate specificity, but leave unanswered questions regarding the mechanism of substrate-gated reactivity with dioxygen.

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Section: Structure Refinement and Analysissupporting

confidence: 63%

Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

York

Sardar

Khadka

et al. 2021

Journal of Biological Chemistry

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“…Some microorganisms are to produce poly(3HP) by engineering microbes, such as bacteria and fungi, as shown in Table 3 ( Jers et al, 2019 ). Choosing the appropriate host to use involves several factors.…”

Section: The Production Host Of Poly(3hp)mentioning

confidence: 99%

Poly(3-hydroxypropionate): Biosynthesis Pathways and Malonyl-CoA Biosensor Material Properties

Aduhene

Cui

Yang

et al. 2021

Front. Bioeng. Biotechnol.

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Many single-use non-degradable plastics are a threat to life today, and several polyhydroxyalkanoates (PHAs) biopolymers have been developed in the bioplastic industry to place petrochemical-based plastics. One of such is the novel biomaterial poly(3-hydroxypropionate) [poly(3HP)] because of its biocompatibility, biodegradability, and high yield synthesis using engineered strains. To date, many bio-polymer-based functional composites have been developed to increase the value of raw microbial-biopolymers obtained from cheap sources. This review article broadly covers poly(3HP), a comprehensive summary of critical biosynthetic production pathways comparing the yields and titers achieved in different Microbial cell Factories. This article also provides extensive knowledge and highlights recent progress on biosensors’ use to optimize poly(3HP) production, some bacteria host adopted for production, chemical and physical properties, life cycle assessment for poly(3HP) production using corn oil as carbon source, and some essential medical applications of poly(3HP).

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“…Recent research has focused on the use of bioengineered microorganisms as well as on improving the recovery of 3‐HPA from the fermentation broth. [ 33,34 ] Alternatively, the direct fermentation of AA from glucose, using biosynthetic pathways similar to the one of 3‐HPA, has recently been reported and may spur more investigations, although obtained titers were at best lower than 0.25 g L −1 of AA. [ 35,36 ]…”

Section: Production Of Biobased Acrylates and Analogsmentioning

confidence: 99%

Production and Polymerization of Biobased Acrylates and Analogs

Fouilloux

Thomas

2021

Macromol. Rapid Commun.

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To prepare biobased polymers, particular attention must be paid to the obtention of the monomers from which they are derived. (Meth)acrylates and their analogs constitute such a class of monomers that have been extensively studied due to the wide range of polymers accessible from them. This review therefore aims to highlight the progresses made in the production and polymerization of (meth)acrylates and their analogs. Acrylic acid production from biomass is close to commercialization, as three different high‐potential intermediates are identified: glycerol, lactic acid, and 3‐hydroxypropionic acid. Biobased methacrylic acid is less common, but several promising options are available, such as the decarboxylation of itaconic acid or the dehydration of 2‐hydroxyisobutyric acid. Itaconic acid is also a vinylic monomer of great interest, and polymers derived from it have already found commercial applications. Methylene butyrolactones are promising monomers, obtained from bioresources via three different intermediates: levulinic, succinic, or itaconic acid. Although expensive, methylene butyrolactones have a strong potential for the production of high‐performance polymers. Finally, β‐substituted acrylic monomers, such as cinnamic, fumaric, muconic, or crotonic acid, are also examined, as they provide an original access to biobased materials from various renewable raw materials, such as protein waste, lignin, or wastewater.

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Production of 3-Hydroxypropanoic Acid From Glycerol by Metabolically Engineered Bacteria

Cited by 37 publications

References 90 publications

Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

Poly(3-hydroxypropionate): Biosynthesis Pathways and Malonyl-CoA Biosensor Material Properties

Production and Polymerization of Biobased Acrylates and Analogs

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