Synthesis of branched and linear 1,4-linked galactan oligosaccharides

Andersen, Mathias Christian Franch; Boos, Irene; Kinnaert, Christine; Awan, Shahid I.; Pedersen, Henriette L.; Kračun, Stjepan Krešimir; Lanz, Gyrithe; Rydahl, Maja Gro; Kjaerulff, Louise; Håkansson, Maria; Kimbung, Raymond; Logan, D.T.; Gotfredsen, Charlotte Held; Willats, William G. T.; Clausen, Mads Hartvig

doi:10.1039/c7ob03035e

“…The main challenge of type I galactans is the low reactivity of the axial hydroxy group at C-4 of the Gal residues. Type I galactans up to 7mer (121a-c) have been prepared employing C-2 O-Piv or O-Ac PG and either n-pentenyl or thioglycoside LG (Figure 10) [331][332][333]. Steric bulk around the unreactive C-4 OH was minimized by using Bn or allyl (All) ethers at C-3 and C-6 positions [331].…”

Section: β-Galactansmentioning

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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A Glycan Array‐Based Assay for the Identification and Characterization of Plant Glycosyltransferases

Ruprecht

¹

,

Bartetzko

²

,

Senf

³

et al. 2020

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Growing plants with modified cell wall compositions is a promising strategy to improve resistance to pathogens, increase biomass digestibility, and tune other important properties. In order to alter biomass architecture, a detailed knowledge of cell wall structure and biosynthesis is a prerequisite. We report here a glycan array‐based assay for the high‐throughput identification and characterization of plant cell wall biosynthetic glycosyltransferases (GTs). We demonstrate that different heterologously expressed galactosyl‐, fucosyl‐, and xylosyltransferases can transfer azido‐functionalized sugar nucleotide donors to selected synthetic plant cell wall oligosaccharides on the array and that the transferred monosaccharides can be visualized “on chip” by a 1,3‐dipolar cycloaddition reaction with an alkynyl‐modified dye. The opportunity to simultaneously screen thousands of combinations of putative GTs, nucleotide sugar donors, and oligosaccharide acceptors will dramatically accelerate plant cell wall biosynthesis research.

show abstract

A Glycan Array‐Based Assay for the Identification and Characterization of Plant Glycosyltransferases

Ruprecht

¹

,

Bartetzko

²

,

Senf

³

et al. 2020

Self Cite

View full text Add to dashboard Cite

Growing plants with modified cell wall compositions is a promising strategy to improve resistance to pathogens, increase biomass digestibility, and tune other important properties. In order to alter biomass architecture, a detailed knowledge of cell wall structure and biosynthesis is a prerequisite. We report here a glycan array‐based assay for the high‐throughput identification and characterization of plant cell wall biosynthetic glycosyltransferases (GTs). We demonstrate that different heterologously expressed galactosyl‐, fucosyl‐, and xylosyltransferases can transfer azido‐functionalized sugar nucleotide donors to selected synthetic plant cell wall oligosaccharides on the array and that the transferred monosaccharides can be visualized “on chip” by a 1,3‐dipolar cycloaddition reaction with an alkynyl‐modified dye. The opportunity to simultaneously screen thousands of combinations of putative GTs, nucleotide sugar donors, and oligosaccharide acceptors will dramatically accelerate plant cell wall biosynthesis research.

show abstract

Synthesis of branched and linear 1,4-linked galactan oligosaccharides

Cited by 5 publications

References 43 publications

Progress and challenges in the synthesis of sequence controlled polysaccharides

Progress and challenges in the synthesis of sequence controlled polysaccharides

A Glycan Array‐Based Assay for the Identification and Characterization of Plant Glycosyltransferases

A Glycan Array‐Based Assay for the Identification and Characterization of Plant Glycosyltransferases

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