Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly

Bartetzko, Max Peter; Schuhmacher, Frank; Seeberger, Peter H.; Pfrengle, Fabian

doi:10.1021/acs.joc.6b02745

Cited by 19 publications

(14 citation statements)

References 31 publications

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“…47 A more time-consuming capping method that incorporates benzoate esters offers an alternative when acetyl caps are not suitable due to acetyl cleavage or migration in subsequent steps. 48,49…”

Section: Aga Approachmentioning

confidence: 99%

“…Synthetic glycans are useful tools for active site mapping and to determine the substrate specificity of enzymes such as hydrolases and transglycosylases. Arabinoxylans, arabinogalactans and mixed-linkage glucans obtained through AGA were applied for determining the substrate specificity of xylan-deconstructing enzymes, 30 endogalactanases 49 and lichenase. 31 To this end, tailor-made carbohydrates with specific substitution patterns were used as enzyme substrates and time-course experiments and HPLC analysis of digestion products were performed.…”

Section: Applications Of Glycans Obtained By Agamentioning

confidence: 99%

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Automated Glycan Assembly: A Perspective

2019

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The intrinsic complexity of carbohydrate structures has hampered access to pure glycans and hence impeded progress in the glycosciences. Automated Glycan Assembly (AGA) has facilitated the procurement of synthetic glycans, to be used in diagnostics, vaccine development, enzyme characterization and structure–function relationship studies. A general approach for obtaining complex glycans from mammalian, bacterial, fungal and plant classes provides molecular tools for glycobiology research. Recent advances in AGA technology pave the way for the production of novel carbohydrate materials. This perspective describes the state-of-the art of AGA and aspects of the technology where additional improvements are needed.

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Section: Aga Approachmentioning

confidence: 99%

Section: Applications Of Glycans Obtained By Agamentioning

confidence: 99%

Automated Glycan Assembly: A Perspective

2019

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“…Type I is present in pectic polysaccharide as a decoration of the main backbone and characterized by β -(1,4) linkages connecting Gal units for the linear chain, and the branching is achieved by α -(1,3) bonds between arabinofuranosides and galactosides. 561 Type II, on the other hand, is present as a highly branched polysaccharide attached to a hydroxyproline-rich peptide structure. The linear backbone of the glycan is based on β -(1,3) linkages, while the branching occurs through β -(1,6) bonds.…”

Section: Automated Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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“…Pfrengle and co-workers produced a set of type I AGs and determined the substrate specificities of three β-(1→4)-endogalactanases. 181 The galactans and type I AGs that have so far been synthesized are presented in Table 17. 183 Andersen et al 179 Lichtenthaler et al 183 Andersen et al 179 Bartetzko et al 181…”

Section: Type I Ags and Galactansmentioning

confidence: 99%

Chemical Synthesis of Oligosaccharides Related to the Cell Walls of Plants and Algae

et al. 2017

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Plant cell walls are composed of an intricate network of polysaccharides and proteins that varies during the developmental stages of the cell. This makes it very challenging to address the functions of individual wall components in cells, especially for highly complex glycans. Fortunately, structurally defined oligosaccharides can be used as models for the glycans, to study processes such as cell wall biosynthesis, polysaccharide deposition, protein-carbohydrate interactions, and cell-cell adhesion. Synthetic chemists have focused on preparing such model compounds, as they can be produced in good quantities and with high purity. This Review contains an overview of those plant and algal polysaccharides that have been elucidated to date. The majority of the content is devoted to detailed summaries of the chemical syntheses of oligosaccharide fragments of cellulose, hemicellulose, pectin, and arabinogalactans, as well as glycans unique to algae. Representative synthetic routes within each class are discussed in detail, and the progress in carbohydrate chemistry over recent decades is highlighted.

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Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly

Cited by 19 publications

References 31 publications

Automated Glycan Assembly: A Perspective

Automated Glycan Assembly: A Perspective

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Chemical Synthesis of Oligosaccharides Related to the Cell Walls of Plants and Algae

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