A traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends

Wilsdorf, Michael; Schmidt, Deborah; Bartetzko, Max Peter; Dallabernardina, Pietro; Schuhmacher, Frank; Seeberger, Peter H.; Pfrengle, Fabian

doi:10.1039/c6cc04954k

Cited by 18 publications

(21 citation statements)

References 24 publications

(5 reference statements)

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“…More likely, the presence of the aminopentyl linker at the reducing end of the oligosaccharides produced by automated glycan assembly influences the way the enzymes deal with these substrates relative to the way they deal with oligosaccharides harboring a free reducing end. The potential influence that such a linker present at the reducing end of a synthetic substrate exerts on the catalytic activity of an enzyme could be reduced in the future, thanks to the development of photo‐cleavable linkers leading to oligosaccharides with free reducing ends . Alternatively, we also suspect that AJA GH5_2‐1 could perform some transglycosylation using the xylotetraose.…”

Section: Discussionmentioning

confidence: 99%

Analyzing the Substrate Specificity of a Class of Long‐Horned‐Beetle‐Derived Xylanases by Using Synthetic Arabinoxylan Oligo‐ and Polysaccharides

2020

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thetic arabinoxylan oligo-and polysaccharides. We demonstrate that AJAGH5_2-1 processes arabinoxylanpolysaccharides in am anner distinct from classical xylanase families such as GH10 and GH11. AJAGH5_2-1i sa ctiveo nl ong oligosaccharides andc leaves at the non-reducing end of as ubstituted xylose residue (position + 1) only if:1 )three xylose residues are present upstream and downstream of the cleavage site, and 2) xylose residues at positions À1, À2, + 2a nd + 3a re not substituted.

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Section: Discussionmentioning

confidence: 99%

Analyzing the Substrate Specificity of a Class of Long‐Horned‐Beetle‐Derived Xylanases by Using Synthetic Arabinoxylan Oligo‐ and Polysaccharides

2020

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“…41,42 Traceless linker 4 , a modified version of linker 3 , was developed to obtain glycans with a free reducing end. 43 The use of chemo-orthogonal methods for cleavage from the solid support produces fully protected oligosaccharides that are easier to purify using NP-HPLC conditions than the partially protected glycans obtained after cleavage of a base-labile linker. Semiprotected glycans greatly vary in terms of solubility and polarity such that finding appropriate conditions for chromatographic separation is time-consuming and difficult to generalize.…”

Section: Aga Approachmentioning

confidence: 99%

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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“…The synthesis of these oligosaccharides required the development of an ew photolabile linker, 16,w ith ab enzylic moiety between the glycan and photolabile moiety (Scheme5). [24] The incorporation of ab enzylic moiety in the linker enabled the tracelessr emoval of the linker in the hydrogenolysis step performed during the final deprotection procedures. After light induced cleavageo ft he glycan from the solid support, followed by global deprotection,n ine plant cellwall oligosaccharides with free reducing ends were obtained.…”

Section: Aga Of Plant Cell-wall Oligosaccharidesmentioning

confidence: 99%

“…Having established reliable AGA procedures for a variety of plant cell wall–related oligosaccharides equipped with an aminoalkyl linker at the reducing end, we have also used the same building blocks to access oligosaccharides with free reducing ends. The synthesis of these oligosaccharides required the development of a new photolabile linker, 16 , with a benzylic moiety between the glycan and photolabile moiety (Scheme ) . The incorporation of a benzylic moiety in the linker enabled the traceless removal of the linker in the hydrogenolysis step performed during the final deprotection procedures.…”

Section: Introductionmentioning

confidence: 99%

Automated Glycan Assembly of Plant Oligosaccharides and Their Application in Cell‐Wall Biology

Bartetzko

Pfrengle

2019

ChemBioChem

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The plant cell wall provides the richest available resource of fermentable carbohydrates and biobased materials. The main component of plant cell walls is cellulose, which is the most abundant biomolecule on earth. Apart from cellulose, which is constructed from relatively simple β‐1,4‐glucan chains, plant cell walls also contain structurally more complex heteropolysaccharides (hemicellulose and pectin), as well as lignin and cell‐wall proteins. A detailed understanding of the molecular structures, functions, and biosyntheses of cell‐wall components is required to further promote their industrial use. Plant cell‐wall research is, to a large degree, hampered by a lsack of available well‐defined oligosaccharide samples that represent the structural features of cell‐wall glycans. One technique to access these oligosaccharides is automated glycan assembly; a technique in which monosaccharide building blocks are, similarly to automated peptide and oligonucleotide chemistry, successively added to a linker‐functionalized resin in a fully automated manner. Herein, recent research into the automated glycan assembly of different classes of cell‐wall glycans used as molecular tools for cell‐wall biology is discussed. More than 60 synthetic oligosaccharides were prepared and printed as microarrays for screening monoclonal antibodies that recognize plant cell‐wall polysaccharides. The synthesized oligosaccharides have also been used to investigate glycosyltransferases and glycoside hydrolases, which are involved in synthesis and degradation of plant cell walls, as well as for the analysis of cell‐wall‐remodeling enzymes.

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A traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends

Cited by 18 publications

References 24 publications

Analyzing the Substrate Specificity of a Class of Long‐Horned‐Beetle‐Derived Xylanases by Using Synthetic Arabinoxylan Oligo‐ and Polysaccharides

Analyzing the Substrate Specificity of a Class of Long‐Horned‐Beetle‐Derived Xylanases by Using Synthetic Arabinoxylan Oligo‐ and Polysaccharides

Automated Glycan Assembly: A Perspective

Automated Glycan Assembly of Plant Oligosaccharides and Their Application in Cell‐Wall Biology

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