Functionalized Celluloses with Regular Substitution Pattern by Glycosynthase-Catalyzed Polymerization

Codera, Victoria; Edgar, Kevin J.; Faijes, Magda; Planas, Antoni

doi:10.1021/acs.biomac.5b01453

Cited by 22 publications

(15 citation statements)

References 37 publications

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“…A different variant of this enzyme, HiCel7B E197A was recently employed in the synthesis of regularly substituted, functionalized celluloses by Codera et al [ 31 ]. Polymerization of 6′-azido-α-cellobiosyl fluoride by HiCel7B E197A resulted in regularly azido substituted cellulose oligosaccharides with a degree of polymerization (DP) up to 32 in a yield of 88%.…”

Section: Glycoside Syntheses Using Glycosynthase Methodsmentioning

confidence: 99%

Synthesis of Glycosides by Glycosynthases

Hayes

Pietruszka

2017

Molecules

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The many advances in glycoscience have more and more brought to light the crucial role of glycosides and glycoconjugates in biological processes. Their major influence on the functionality and stability of peptides, cell recognition, health and immunity and many other processes throughout biology has increased the demand for simple synthetic methods allowing the defined syntheses of target glycosides. Additional interest in glycoside synthesis has arisen with the prospect of producing sustainable materials from these abundant polymers. Enzymatic synthesis has proven itself to be a promising alternative to the laborious chemical synthesis of glycosides by avoiding the necessity of numerous protecting group strategies. Among the biocatalytic strategies, glycosynthases, genetically engineered glycosidases void of hydrolytic activity, have gained much interest in recent years, enabling not only the selective synthesis of small glycosides and glycoconjugates, but also the production of highly functionalized polysaccharides. This review provides a detailed overview over the glycosylation possibilities of the variety of glycosynthases produced until now, focusing on the transfer of the most common glucosyl-, galactosyl-, xylosyl-, mannosyl-, fucosyl-residues and of whole glycan blocks by the different glycosynthase enzyme variants.

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Section: Glycoside Syntheses Using Glycosynthase Methodsmentioning

confidence: 99%

Synthesis of Glycosides by Glycosynthases

Hayes

Pietruszka

2017

Molecules

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“…Such alternating 6-azido-6-deoxycelluloses can be acetylated then subsequently reduced to amines. Conversely, alternating 6-azido-6-deoxycelluloses can undergo copper(I)-catalysed azide-alkyne cycloaddition (CuAAc - click chemistry) with Alexa Fluor 488 Alkyne to form conjugated alternating 6-azido-6-deoxycellulose [ 77 ].…”

Section: Glycoside Hydrolasesmentioning

confidence: 99%

Recent advances in enzymatic synthesis of β-glucan and cellulose

Andrade

Field

et al. 2021

Carbohydrate Research

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Bottom-up synthesis of β-glucans such as callose, fungal β-(1,3)(1,6)-glucan and cellulose, can create the defined compounds that are needed to perform fundamental studies on glucan properties and develop applications. With the importance of β-glucans and cellulose in high-profile fields such as nutrition, renewables-based biotechnology and materials science, the enzymatic synthesis of such relevant carbohydrates and their derivatives has attracted much attention. Here we review recent developments in enzymatic synthesis of β-glucans and cellulose, with a focus on progress made over the last five years. We cover the different types of biocatalysts employed, their incorporation in cascades, the exploitation of enzyme promiscuity and their engineering, and reaction conditions affecting the production as well as in situ self-assembly of (non)functionalised glucans. The recent achievements in the application of glycosyl transferases and β-1,4- and β-1,3-glucan phosphorylases demonstrate the high potential and versatility of these biocatalysts in glucan synthesis in both industrial and academic contexts.

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“…Cellulose–xylan [ 80 ] and cellulose–chitin [ 81 ] hybrids were also obtained upon enzymatic polymerization of the respective dimers. An amino or azido functionality in the C-6 position allows for further modifications, for example by click-chemistry [ 82 ]. These results show that enzymatic methods can be powerful approaches also to create unnatural polysaccharide materials.…”

Section: Reviewmentioning

confidence: 99%

Progress and challenges in the synthesis of sequence controlled polysaccharides

Fittolani¹,

Tyrikos‐Ergas²,

Vargová³

et al. 2021

Beilstein J. Org. Chem.

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The sequence, length and substitution of a polysaccharide influence its physical and biological properties. Thus, sequence controlled polysaccharides are important targets to establish structure–properties correlations. Polymerization techniques and enzymatic methods have been optimized to obtain samples with well-defined substitution patterns and narrow molecular weight distribution. Chemical synthesis has granted access to polysaccharides with full control over the length. Here, we review the progress towards the synthesis of well-defined polysaccharides. For each class of polysaccharides, we discuss the available synthetic approaches and their current limitations.

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Functionalized Celluloses with Regular Substitution Pattern by Glycosynthase-Catalyzed Polymerization

Cited by 22 publications

References 37 publications

Synthesis of Glycosides by Glycosynthases

Synthesis of Glycosides by Glycosynthases

Recent advances in enzymatic synthesis of β-glucan and cellulose

Progress and challenges in the synthesis of sequence controlled polysaccharides

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