Reactivity‐Based One‐Pot Synthesis of the Tumor‐Associated Antigen N3 Minor Octasaccharide for the Development of a Photocleavable DIOS‐MS Sugar Array

Lee, Jinq‐Chyi; Wu, Chung‐Yi; Apon, Junefredo V.; Siuzdak, Gary; Wong, Chi‐Huey

doi:10.1002/anie.200504067

Cited by 62 publications

(28 citation statements)

References 31 publications

(14 reference statements)

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“…32 Parts B and C of Figure 3 showed that these glycan arrays had retained their sugar-protein binding patterns 35 when VK-9 (a mouse anti-Globo H monoclonal antibody) and anti-SSEA-3 monoclonal antibody were used for binding studies, respectively.…”

Section: Resultsmentioning

confidence: 99%

Glycan Array on Aluminum Oxide-Coated Glass Slides through Phosphonate Chemistry

et al. 2010

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A new type of glycan array covalently or noncovalently attached to aluminum oxide-coated glass (ACG) slides has been developed for studies of enzymatic reactions and protein binding. To prepare the noncovalent array, glycans with a polyfluorinated hydrocarbon (-C(8)F(17)) tail are spotted robotically onto the ACG slide surface containing a layer of polyfluorinated hydrocarbon terminated with phosphonate. After incubation and washing, the noncovalent array can be characterized by MS-TOF via ionization/desorption at a low laser energy without addition of matrix. A representative cellotetraose array was developed to study the activity and specificity of different cellulases and to differentiate the exo- and endoglucanase activities. To prepare the covalent array, glycans with a phosphonic acid tail were synthesized and spotted robotically onto the ACG slide surface. After incubation, the slides can be used directly for quantitative protein binding analysis. Compared to the preparation of glycan arrays on glass slides and other surfaces, this method of arraying using phosphonic acid reacting with ACG is more direct, convenient, and effective and represents a new platform for the high-throughput analysis of protein-glycan interactions.

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Section: Resultsmentioning

confidence: 99%

Glycan Array on Aluminum Oxide-Coated Glass Slides through Phosphonate Chemistry

et al. 2010

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“…In the programmable reactivity based chemoselective glycosylation, RRVs methanol were utilized as a quantitative measure to guide building block selection 2, 5, 6, 10, 11, 14, 15. However, in some cases, glycosylation yields were lower than those indicated based on RRV methanol differentials,11, 40 which could be due to the decrease of chemoselectivity resulting from glycosylating a less reactive carbohydrate acceptor.…”

Section: Resultsmentioning

confidence: 99%

Thio-arylglycosides with various aglyconpara-substituents: a probe for studying chemical glycosylation reactions

Huang

et al. 2009

Org. Biomol. Chem.

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Summary Three series of thioglycosyl donors differing only in their respective aglycon substituents within each series have been prepared as representatives of typical glycosyl donors. The relative anomeric reactivities of these donors were quantified under competitive glycosylation conditions with various reaction time, promoters, solvents and acceptors. Over three orders of magnitude reactivity difference were generated by simple transformation of the para-substituent on the aglycon with methanol as the acceptor, while chemoselectivities became lower with carbohydrate acceptors. Excellent linear correlations were attained between relative reactivity values of donors and σp values of the substituents in the Hammett plots. This indicates that the glycosylation mechanism remains the same over a wide range of reactivities and glycosylation conditions. The negative slopes of the Hammett plots suggested that electron donating substituents expedite the reactions and the magnitudes of slopes can be rationalized by neighboring group participation as well as electronic properties of the glycon protective groups. Within the same series of donors, less nucleophilic acceptors gave smaller slopes in their Hammett plots. This is consistent with the notion that acceptor nucleophilic attack onto the reactive intermediate is part of the rate limiting step of the glycosylation reaction. Excellent linear Hammett correlations were obtained between relative reactivity values of three series of donors differing only in their aglycon substituents and σp values of the substituents.

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“…As such an extension to methanol/ water mixtures may be rather general, this will simplify the synthesis of a wide variety of oligosaccharides that are of interest to be attached onto solid substrates for sensing or diagnostics purposes, as in carbohydrate arrays. 65,66 A full ab initio assignment was made of all 1 H and 13 C chemical shifts in the 900 MHz NMR spectra of the synthesized compounds GM3, GM2 and GM1 derivatives 8, 11 and 14. This approach will also allow for the full assignment of the sugar moieties of other (naturally occurring) glycolipids.…”

Section: Resultsmentioning

confidence: 99%

GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis

Pukin

Weijers

Lagen

et al. 2008

Carbohydrate Research

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Abstract-Undec-10-enyl, undec-10-ynyl and 11-azidoundecyl glycoside analogues corresponding to the oligosaccharides of human gangliosides GM3, GM2 and GM1 were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. Due to poor water solubility of the substrates, the reactions were carried out in methanol-water media, which for the first time were shown to be compatible with the C. jejuni a-(2?3)-sialyltransferase (CST-06) and b-(1?4)-N-acetylgalactosaminyltransferase (CJL-30). Bioequivalence of our synthetic analogues and natural gangliosides was examined by binding to Vibrio cholerae toxin and to the B subunit of Escherichia coli heat-labile enterotoxin. This bioequivalence was confirmed by binding mouse and human monoclonal antibodies to GM1 and acute phase sera containing IgM and IgG antibodies to GM1 from patients with the immune-mediated polyneuropathy Guillain-Barré syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with 13 C-1 H correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all 1 H and 13 C chemical shifts is presented.

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Reactivity‐Based One‐Pot Synthesis of the Tumor‐Associated Antigen N3 Minor Octasaccharide for the Development of a Photocleavable DIOS‐MS Sugar Array

Cited by 62 publications

References 31 publications

Glycan Array on Aluminum Oxide-Coated Glass Slides through Phosphonate Chemistry

Glycan Array on Aluminum Oxide-Coated Glass Slides through Phosphonate Chemistry

Thio-arylglycosides with various aglyconpara-substituents: a probe for studying chemical glycosylation reactions

GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis

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