Simultaneous and selective decarboxylation of l-serine and deamination of l-phenylalanine in an amino acid mixture—a means of separating amino acids for synthesizing biobased chemicals

Teng, Yinglai; Scott, Elinor L.; Dijk, Susan C. M. Witte‐van; Sanders, J.P.M.

doi:10.1016/j.nbt.2015.04.006

Cited by 14 publications

(16 citation statements)

References 29 publications

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“…In the next sections various (bio)chemical conversion technologies for amino acids will be discussed (Figure ). Depending on the conversion technology and the target products, the substrate scope comprises either one amino acid, a selected mixture of amino acids or the entire protein hydrolysate …”

Section: Availability and Pretreatment Of Raw Materialsmentioning

confidence: 99%

“…Process intensification has been achieved by immobilizing the enzyme in solid porous materials, which in turn can be embedded in a mixed matrix membrane system . Similarly, lysine decarboxylase was applied in the separation of the basic amino acids lysine and arginine, and the fractionation of serine, phenylalanine, and methionine was achieved by the combined action of serine decarboxylase and phenylalanine ammonia lyase (see Section 4.2.2.1) …”

Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

“…Ammonia lyases catalyze the deamination of certain amino acids to α,β‐unsaturated carboxylic acids, for example, phenylalanine to cinnamic acid, tyrosine to p ‐coumaric acid, and aspartic acid to fumaric acid . However, the number of these enzymes is rather limited and they are characterized by a very high substrate specificity .…”

Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

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Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

et al. 2019

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Protein‐rich biomass provides a valuable feedstock for the chemical industry. This Review describes every process step in the value chain from protein waste to chemicals. The first part deals with the physicochemical extraction of proteins from biomass, hydrolytic degradation to peptides and amino acids, and separation of amino acid mixtures. The second part provides an overview of physical and (bio)chemical technologies for the production of polymers, commodity chemicals, pharmaceuticals, and other fine chemicals. This can be achieved by incorporation of oligopeptides into polymers, or by modification and defunctionalization of amino acids, for example, their reduction to amino alcohols, decarboxylation to amines, (cyclic) amides and nitriles, deamination to (di)carboxylic acids, and synthesis of fine chemicals and ionic liquids. Bio‐ and chemocatalytic approaches are compared in terms of scope, efficiency, and sustainability.

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Section: Availability and Pretreatment Of Raw Materialsmentioning

confidence: 99%

Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

Section: Amino Acids As Direct Precursors To Value‐added Chemicalsmentioning

confidence: 99%

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Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

et al. 2019

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“…The deamination of amino acids is primarily accomplished by the following four amino acids enzymes: dehydrogenase, lyase, oxidase, and transaminase (Fig. 1A) 24–26. The common reaction characteristic of these four enzymes is the production of NH 3 as a byproduct except in the transamination reaction, in which amine is assimilated to the amine acceptor molecule 6, 10.…”

Section: Biological Deamination Of Amino Acid With Nh3releasementioning

confidence: 99%

Nitrogen‐Neutral Amino Acids Refinery: Deamination of Amino Acids for Bio‐Alcohol and Ammonia Production

Choi

2021

ChemBioEng Reviews

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Amino acids are a valuable bioresource that contains both the acid form of carbon and the amine group of nitrogen. Amino acids not only constitute proteins and the building blocks for living organisms but also provide a key intermediate for controlling the nitrogen balance in cells. The production of amino acids using microorganisms has, along with the development of biotechnology, created a large market for biochemicals. In parallel, there have been various biochemical production methods using pulmonary proteins or direct amino acids as biomass through enzymatic bioconversion or whole‐cell biotransformation. The deamination of amino acids facilitated the applications of 2‐keto and acrylic acids, in particular, for biofuels of bio alcohol, pharmaceuticals, cosmetics, as building blocks for polymers, and other versatile industrial chemicals. In this review, we report on the application of amino acids derived from biochemicals initiated by deamination reactions using deaminase, ammonia‐lyase, and oxidase enzymes for biotechnology applications.

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“…12 This reaction may therefore be particularly attractive regarding the chemocatalytic upgrading of protein-rich biomass into nitrogenous chemicals, being highly complementary to recently developed strategies for selective defunctionalization of amino acids. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] The reduction of carboxylic acids is not straightforward. Transition-metal catalyzed hydrogenation, where nucleophilic hydride species are produced in situ by the dissociation of molecular hydrogen (H2), is the most attractive approach in terms of green chemistry because only water is generated as a co-product.…”

Section: Introductionmentioning

confidence: 99%

Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates

Vandekerkhove

Claes

Schouwer

et al. 2018

ACS Sustainable Chem. Eng.

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While protein-rich biomass waste is nowadays mainly used for animal feed, conversion of its amino acid constituents to nitrogenous chemicals is a potential higher value route. To that end, the hydrogenation of amino acids to amino alcohols was studied in this work. Using a bimetallic Rh-MoOx/SiO2 catalyst, glutamic acid was for the first time hydrogenated to the aminodiol in high yield. By minimizing partial reduction and consecutive hydrogenolysis, and by suppressing the competitive cyclization to pyroglutamic acid (and derivatives thereof), glutamidiol was obtained in 77% yield at 70 bar H2 and 80 °C. High yields (typically > 80%) and selectivities were also achieved for most other natural amino acids, except for the S-containing amino acids 2 cysteine and methionine, which act as catalyst poisons. This limitation was overcome by applying a simple oxidation step with performic acid prior to the hydrogenation. The system was applied successfully to a mixture of amino acids obtained by hydrolysis of pre-oxidized bovine serum albumin. Amino alcohols were produced with high overall conversion (> 90%) and selectivity (88%) without the need for an intermediate, expensive and difficult separation step. The reaction proceeds with very high atom economies for both carbon and nitrogen, and generates only water as a by-product.

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Simultaneous and selective decarboxylation of l-serine and deamination of l-phenylalanine in an amino acid mixture—a means of separating amino acids for synthesizing biobased chemicals

Cited by 14 publications

References 29 publications

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities

Nitrogen‐Neutral Amino Acids Refinery: Deamination of Amino Acids for Bio‐Alcohol and Ammonia Production

Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates

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