Glycoprotein Synthesis: From Glycobiological Tools to Tailor-made Catalysts

Davis, Benjamin G.; Jones, J. Bryan

doi:10.1055/s-1999-2865

Cited by 19 publications

(11 citation statements)

References 104 publications

(128 reference statements)

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“…Among protein conjugates involved in a variety of inter‐cell communication events, glycoproteins are of special importance 15. The type and the position of carbohydrate moieties determine protein folding, receptor binding, intercellular transport, microbial virulence and host immune responses.…”

Section: Introductionmentioning

confidence: 99%

Tracing glycoprotein structures: electrospray ionization tandem mass spectrometric analysis of sugar–peptide adducts

et al. 2002

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Owing to the diversity of carbohydrate structures and their significance for the function of many biopolymers, structural analysis of various carbohydrate-related compounds is of great importance. Electrospray ionization tandem mass spectrometry (ESI-MS/MS) was used to establish the fragmentation behaviour of a range of sugar-peptide adducts as model compounds of widespread glycoprotein structures. The compounds used in this study were chosen to provide correlation of distinct fragment ions with specific structural differences, namely position and type of carbohydrate-peptide bond and structure of the sugar moiety. All compounds show N- and C-terminal sequence ions along with losses of up to three water molecules. Fructose-related Amadori compounds exhibit M + 78 modified N-terminal peptide fragment ions. Fragmentation of glucose-peptide esters is characterized by the sugar ring fragmentation. Additionally, under the ESI-MS conditions applied, the esters studied undergo intramolecular reaction giving cyclic sugar-peptide structures that can be traced by the presence of N-terminal peptide M + 42 adducts. Detailed analysis of cyclic fructose-related compound comprising structural features of both studied groups revealed a rich fragmentation pattern derived from amino acid residues and water molecules losses from [M - 2H(2)O + H](+) ion. Also, some interesting differences were found with respect to the nature of carbohydrate moieties.

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Section: Introductionmentioning

confidence: 99%

Tracing glycoprotein structures: electrospray ionization tandem mass spectrometric analysis of sugar–peptide adducts

et al. 2002

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“…To address this need for homogeneous glycoproteins, we have been working to develop new methods for the synthesis of glycopeptide mimetics. , Ideally, the designed analogues should be more easily generated than the corresponding native structures yet possess the desired biological activity. Mindful of the importance of the core GalNAc(α1- O )Ser/Thr for establishing proper organization of the glycopeptide backbone, we sought to preserve this structural element.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Elaboration of O-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAc

Marcaurelle

Bertozzi

2001

J. Am. Chem. Soc.

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A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was incorporated into a peptide by fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Higher order oligosaccharides were readily generated by alkylation of the corresponding 3-thioGalNAc with N-bromoacetamido sugars. The rapid assembly of "core 1"and "core 3" O-linked glycopeptide mimetics was accomplished in this fashion.

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“…Benzyl ether (2) and fluorinated benzyl ethers (3)(4)(5)(6)(7) were synthesized by the reaction of methyl-α-Dmannopyronoside (1) with various benzyl bromides using Williamson ether synthesis method. The spectral analysis showed that the methylene carbons of the fluorinated benzyl ethers showed a significant shift to a high field region compared to the methylene carbons of non-fluorinated benzyl ether in the 13 C NMR spectra.…”

Section: Discussionmentioning

confidence: 99%

“…Oligosaccharides have exhibited important role in cell-cell interactions, which has had several positive implications. [1][2][3][4][5] The key reaction involved in the synthesis of oligosaccharides is a bond formation between the anomeric center of a saccharide and a hydroxyl group from another sugar molecule. In order to synthesize oligosaccharides from monosaccharide units, the hydroxyl groups present in the monosaccharides have to be protected by the suitable protecting groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Fluorinated Benzyl Ethers as Alternate Protecting Groups for Enhanced NMR Resolution in Oligosaccharide Synthesis

Khoabane

Grayson

Kenwright

et al. 2022

Fine Chemical Engineering

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Oligosaccharides have been playing an important role in biological systems. Synthesis of oligosaccharides requires the protection from hydroxyl groups present in the corresponding monosaccharide units. The existing methods of protection have drawbacks, including formation of anomeric mixtures, change in hydrophilicity or lipophilicity and solubility of the products, participation of the protecting groups in the reactions of the core of monosaccharide units, problems associated with chemoselectivity, regioselectivity and overall stereochemical outcomes of reactions. Additionally, there has been a spectral overlap of these protecting groups with carbohydrate core, which yielded more complex spectra. Therefore, the identification and synthesis of suitable alternative protecting groups have received attention in the oligosaccharide synthesis. The objective of the present study was to synthesize various fluorinated benzyl ethers of methyl-α-D-mannopyronoside and to evaluate these ethers as the alternative protecting groups for enhancing NMR resolution in the oligosaccharide synthesis. Various fluorinated benzyl ethers of methyl-α-D-mannopyronoside were prepared through the reaction of methyl-α-D-mannopyronoside with various fluorinated benzyl bromides by using Williamson ether synthesis method. Spectral analysis of these fluorinated benzyl ethers showed that the peaks of methylene carbons shifted to a value of 10-20 parts per million (ppm) to a high field region in the 13C NMR, compared to the non-fluorinated benzyl ether. As a result, the spectral complexity decreased and enhanced the spectral resolution. In this study, we concluded that fluorinated benzyl ethers could be a suitable alternative to the non-fluorinated benzyl ethers to protect the hydroxyl groups of monosaccharides in the synthesis of oligosaccharides.

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Glycoprotein Synthesis: From Glycobiological Tools to Tailor-made Catalysts

Cited by 19 publications

References 104 publications

Tracing glycoprotein structures: electrospray ionization tandem mass spectrometric analysis of sugar–peptide adducts

Tracing glycoprotein structures: electrospray ionization tandem mass spectrometric analysis of sugar–peptide adducts

Chemoselective Elaboration of O-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAc

Synthesis and Evaluation of Fluorinated Benzyl Ethers as Alternate Protecting Groups for Enhanced NMR Resolution in Oligosaccharide Synthesis

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