On the Splitting of the Side Chain from Tyrosine by the Action of Aldehydes

Akabori, Shirô; Ohno, Ko

doi:10.2183/pjab1945.26.6_39

Cited by 3 publications

(5 citation statements)

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“…The first enzymatic isomerization of monosaccharides was performed in 1952, where studies were conducted to corroborate the enzymatic interconversion of erythrose to erythrulose in the presence of a rabbit muscle. − In 1953, Hochster and Watson found a specific enzyme called xylose isomerase in Pseudomoaas hydrophil , which can catalyze the interconversion of the C5 sugars d -xylose to d -xylulose . Moreover, these authors have also reported that an enzyme called xylose isomerase was unable to isomerize aldoses other than xylose.…”

Section: Biocatalytic Processesmentioning

confidence: 99%

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

et al. 2017

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The well-known interconversion of aldoses to their corresponding ketoses was discovered more than a century ago, but has recently attracted renewed attention due to alternative application areas. Since the pioneering discovery, much work has been directed toward improving the process of isomerization of aldoses in terms of yields, catalysts, solvents, catalytic systems, etc., by both enzymatic and chemo-catalytic approaches. Among aldose–ketose interconversion reactions, fructose production by glucose isomerization to make high-fructose corn syrup (HFCS) is an industrially important and large biocatalytic process today, and a large number of studies have been reported on the process development. In parallel, also alternative chemo-catalytic systems have emerged, as enzymatic conversion has drawbacks, though they are typically more selective and produce fructose under mild reaction conditions. Isomerization of glucose is also a central reaction for making renewable platform chemicals, such as lactic acid, 5-hydroxymethylfurfural (HMF), and levulinic acid. In these other applications, thermally stable catalysts are required, thus making use of enzymatic catalysis inadequate, since enzymes generally possess a limited temperature operating window, typically less than 80 °C. From this viewpoint, the chemo-catalystsespecially solid heterogeneous catalystsare playing a key role for the development of not only making HFCS, but also making chemicals and fuels from glucose via the isomerized product/intermediate fructose. This review focuses on how both enzyme- and chemo-catalysts are being useful for the isomerization of glucose to fructose. Specifically, development of Lewis acid-containing zeolites for glucose isomerization is reviewed in detail, including mechanism, isotopic labeling, and computational studies.

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Section: Biocatalytic Processesmentioning

confidence: 99%

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

et al. 2017

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“…Dupuis and Benezra suggested that a conjugate is formed by a Michael addition (1,4-addition) of cinnamaldehyde to the free amino groups in lysine residues . It is also well-known that phenols condense readily with aldehydes at their ortho- and para-positions, forming resinous materials. , This kind of reaction could also take place between tyrosine residues and cinnamaldehyde. Another possible cross-linking reaction is believed to occur at acidic pH levels, below pH 2–3, because some methylene cross-linking may occur between pairs of amide groups, leading to a doubling of the MW in gliadins…”

Section: Introductionmentioning

confidence: 99%

Biochemical Properties of Bioplastics Made from Wheat Gliadins Cross-Linked with Cinnamaldehyde

Balaguer

Gómez-Estaca

Gavara

et al. 2011

J. Agric. Food Chem.

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The aim of this work has been to study the modification of gliadin films with cinnamaldehyde as a potential cross-linker agent. The molecular weight profile and cross-linking density showed that cinnamaldehyde increased reticulation in the resulting films. The participation of free amino groups of the protein in the newly created entanglements could be a possible mechanism of connection between the polypeptidic chains. The combination of a Schiff base and a Michael addition is a feasible approach to understanding this mechanism. The protein solubility in different media pointed to lower participation by both noncovalent and disulfide bonds in stabilizing the structure of the cross-linked films. The new covalent bonds formed by the cinnamaldehyde treatment hampered water absorption and weight loss, leading to more water-resistant matrices which had not disintegrated after 5 months. The properties of this novel bioplastic could be modified to suit the intended application by using cinnamaldehyde, a naturally occurring compound.

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“…Figure shows possible reaction mechanisms for covalent cross-linking of cinnamaldehyde with protein. Basically, cinnamaldehyde possesses two electrophilic groups that could react directly with proteins via two different mechanisms, i.e., Schiff base formation to free amino groups of protein or Michael addition to nucleophilic groups, i.e., thiol groups of cysteine residues and amino groups of lysine residues. − Also, aldehyde groups of cinnamaldehyde can react with phenol groups of tyrosine residues readily that resulted in cross-linking . Considering one of the ideal applications of KP resin in fiber-reinforced composites, a sheet made with 5% sorbitol was selected as the control for noncross-linked specimens as the optimum amount of plasticizer due to its highest tensile strength and modulus with moderate fracture strain.…”

Section: Resultsmentioning

confidence: 99%

“…Possible reaction mechanisms involved in covalent cross-linking of karanja protein by cinnamaldehyde via (a) Schiff base formation between cinnamaldehyde and primary amine, (b) nucleophilic attack on the β-unsaturated carbon via a 1,4-Michael addition reaction, and (c) phenol groups of tyrosine residues with cinnamaldehyde − …”

Section: Resultsmentioning

confidence: 99%

“…49−51 Also, aldehyde groups of cinnamaldehyde can react with phenol groups of tyrosine residues readily that resulted in crosslinking. 52 Considering one of the ideal applications of KP resin in fiber-reinforced composites, a sheet made with 5% sorbitol was selected as the control for noncross-linked specimens as the optimum amount of plasticizer due to its highest tensile strength and modulus with moderate fracture strain. The crosslinker has been varied between 0% and 16% (on dry protein wt) in 5% sorbitol-plasticized KP sheets.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Green Resin from Forestry Waste Residue “Karanja (Pongamia pinnata) Seed Cake” for Biobased Composite Structures

Rahman

Netravali

2014

ACS Sustainable Chem. Eng.

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A nonedible protein was extracted from defatted karanja (Pongamia pinnata) seedcake, so far considered as forestry waste residue after oil extraction. High average molecular weight and availability of reactive amino groups of karanja protein (KP), which can be cross-linked, provide the basis to form strong polymeric material. Green thermoset resin was developed from KP using a natural α,β-unsaturated aldehyde "cinnamaldehyde". In addition, a natural plasticizer (sorbitol) was used to reduce the brittleness of the resin. Mechanical and physical properties were characterized by solution casting resin films. The cross-linking and plasticizer content were optimized to get the best overall performance. A combination of 5% plasticizer content and 12% cross-linking resulted in best mechanical properties. The modified KP resin provides a green, sustainable, and biobased alternative to not only the petroleum-based resins but also to the edible protein-based resins such as soy protein. The KP resin would be inexpensive and useful to fabricate biobased green composite structures.

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On the Splitting of the Side Chain from Tyrosine by the Action of Aldehydes

Cited by 3 publications

References 0 publications

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

Biochemical Properties of Bioplastics Made from Wheat Gliadins Cross-Linked with Cinnamaldehyde

Green Resin from Forestry Waste Residue “Karanja (Pongamia pinnata) Seed Cake” for Biobased Composite Structures

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