Enzymatic production of all fourteen partially acetylated chitosan tetramers using different chitin deacetylases acting in forward or reverse mode

Hembach, Lea; Cord‐Landwehr, Stefan; Moerschbacher, Bruno M.

doi:10.1038/s41598-017-17950-6

Cited by 67 publications

(62 citation statements)

References 44 publications

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“…Chitosan is produced from chitin either by alkaline deacetylation, which involves boiling (100 °C) chitin in concentrated alkali for several hours (Alishahi & Aïder, ) or by chitin deacetylases (Hembach, Cord‐Landwehr, & Moerschbacher, ). In nature, chitin exists as a linear structured polysaccharide of N‐ acetyl‐ d ‐glucosamine, which has three polymorphic forms, known as α‐, β‐, and γ‐chitin, based on different microfibril orientations (Lodhi et al., ; Tharanathan, ).…”

Section: Chitosan and Chitooligosaccharidementioning

confidence: 99%

Natural Preservatives for Extending the Shelf‐Life of Seafood: A Revisit

Olatunde

Benjakul

2018

Comp Rev Food Sci Food Safe

182

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Consumer demand for minimally processed seafood that retains its sensory and nutritional properties after handling and storage is increasing. Nevertheless, quality loss in seafood occurs immediately after death, during processing and storage, and is associated with enzymatic, microbiological, and chemical reactions. To maintain the quality, several synthetic additives (preservatives) are promising for preventing the changes in texture and color, development of unpleasant flavor and rancid odor, and loss of nutrients of seafood during storage at low temperature. However, the use of these preservatives has been linked to potential health hazards. In this regard, natural preservatives with excellent antioxidant and antimicrobial properties have been extensively searched and implemented as safe alternatives in seafood processing, with the sole purpose of extending shelf‐life. Natural preservatives commonly used include plants extracts, chitosan and chitooligosaccharide, bacteriocins, bioactive peptides, and essential oils, among others. This review provides updated information about the production, mode of action, applications, and limitations of these natural preservatives in seafood preservation.

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Section: Chitosan and Chitooligosaccharidementioning

confidence: 99%

Natural Preservatives for Extending the Shelf‐Life of Seafood: A Revisit

Olatunde

Benjakul

2018

Comp Rev Food Sci Food Safe

182

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“…These enzymes can be used for the production of the fully defined paCOS required for advancing our understanding of molecular structure-function relationships and cellular modes of action of biologically active, partially acetylated chitosans. The portfolio of defined paCOS that can be produced using CDAs has been drastically increased with the realisation that these enzymes can also be used to catalyse the reverse reaction, i.e., the N -acetylation of fully de-acetylated glucosamine oligomers (Dn) in the presence of excess amounts of acetate, while mainly retaining their regio-selectivity [ 33 , 34 ].…”

Section: Regio-selective Chitin De- N -Acteylasmentioning

confidence: 99%

“…The third, ω-mono-de-acetylated paCOS, AAD, is more difficult to produce as no CDA with regio-selectivity for the GlcNAc unit at the reducing end has been described so far. However, if NodB and VcCDA are used in reverse on the fully deacetylated glucosamine trimer D3 in the presence of excess amounts of acetate, they retain their regio-selectivity, so that their combined use will yield AAD [ 34 ].…”

Section: Preparation Of Pacos Trimersmentioning

confidence: 99%

“…Similarly, there are three different mono-acetylated paCOS (A1D2) which can be produced in mirror routes to the ones described above. Reverse α-action of NodB on D3 will yield ADD, while reverse β-action of VcCDA will yield DAD [ 34 ]. The third, ω-mono-acetylated trimer, DDA, can be produced by the joint forward activity of the two enzymes on the fully acetylated trimer A3 [ 34 ].…”

Section: Preparation Of Pacos Trimersmentioning

confidence: 99%

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Preparation of Defined Chitosan Oligosaccharides Using Chitin Deacetylases

Bonin

Sreekumar

Cord‐Landwehr

et al. 2020

IJMS

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During the past decade, detailed studies using well-defined ‘second generation’ chitosans have amply proved that both their material properties and their biological activities are dependent on their molecular structure, in particular on their degree of polymerisation (DP) and their fraction of acetylation (FA). Recent evidence suggests that the pattern of acetylation (PA), i.e., the sequence of acetylated and non-acetylated residues along the linear polymer, is equally important, but chitosan polymers with defined, non-random PA are not yet available. One way in which the PA will influence the bioactivities of chitosan polymers is their enzymatic degradation by sequence-dependent chitosan hydrolases present in the target tissues. The PA of the polymer substrates in conjunction with the subsite preferences of the hydrolases determine the type of oligomeric products and the kinetics of their production and further degradation. Thus, the bioactivities of chitosan polymers will at least in part be carried by the chitosan oligomers produced from them, possibly through their interaction with pattern recognition receptors in target cells. In contrast to polymers, partially acetylated chitosan oligosaccharides (paCOS) can be fully characterised concerning their DP, FA, and PA, and chitin deacetylases (CDAs) with different and known regio-selectivities are currently emerging as efficient tools to produce fully defined paCOS in quantities sufficient to probe their bioactivities. In this review, we describe the current state of the art on how CDAs can be used in forward and reverse mode to produce all of the possible paCOS dimers, trimers, and tetramers, most of the pentamers and many of the hexamers. In addition, we describe the biotechnological production of the required fully acetylated and fully deacetylated oligomer substrates, as well as the purification and characterisation of the paCOS products.

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“…To overcome these drawbacks in the preparation of chitosan, an innovative enzymatic method that exploits chitin deacetylases has been explored: enzymatic chitin. Hembach et al with their research conducted in 2017, have chosen fungal, viral and bacterial chitin deacetylases, producing 14 possible partially acetylated chitosan tetramers with a defined degree of acetylation and pattern of acetylation, also presenting a purification method[158].…”

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confidence: 99%

Chitin and Chitosans: Characteristics, Eco-Friendly Processes and Applications in Cosmetic Science

Casadidio

Peregrina

Gigliobianco

et al. 2019

Preprint

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Huge amounts of chitin and chitosans can be found in the biosphere as important constituent of the exoskeleton of many organisms, as well as waste by worldwide seafood companies. Nowadays, politicians, environmentalists, and industrialists encouraged the use of these marine polysaccharides as renewable source, particularly when developed by alternative eco-friendly processes, especially in the production of regular cosmetics. The aim of this review is to outline the physicochemical and biological properties and the different bioextraction methods of chitin and chitosans sources, focusing on enzymatic deproteinization, bacteria fermentation, and enzymatic deacetylation methods. Thanks to their biodegradability, non-toxicity, biocompatibility, and bioactivity, the application of these marine polymers is widely used in the contemporary manufacturing of biomedical and pharmaceutical products. In the end, advanced cosmetic products based on chitin and chitosans are presented, analyzing different therapeutic aspects about skin, hair, nail, and oral care. The innovative formulations described can be considered as excellent solutions regarding problems in the various body anatomical sectors.

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Enzymatic production of all fourteen partially acetylated chitosan tetramers using different chitin deacetylases acting in forward or reverse mode

Cited by 67 publications

References 44 publications

Natural Preservatives for Extending the Shelf‐Life of Seafood: A Revisit

Natural Preservatives for Extending the Shelf‐Life of Seafood: A Revisit

Preparation of Defined Chitosan Oligosaccharides Using Chitin Deacetylases

Chitin and Chitosans: Characteristics, Eco-Friendly Processes and Applications in Cosmetic Science

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