Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

Roychoudhury, Rajarshi; Pohl, Nicola L. B.

doi:10.1021/ol500023y

Cited by 16 publications

(7 citation statements)

References 40 publications

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“…[13] In addition, many other automated approaches towards chemical glycosylation were also developed to produce oligosaccharides, [14] such as a HPLC-based automated system, [15] Yoshida’s electrolysis cell-based automated system, and a Fluorous-tag solid phase system. [16] Nevertheless, chemical glycosylations suffer from tedious protection/deprotection manipulations. By comparison, enzymatic reactions are advantageous in both efficiency and specificity.…”

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confidence: 99%

Machine‐Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer

et al. 2018

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For decades, researchers have endeavored to develop a general automation system to synthesize oligosaccharides comparable to the preparation of oligonucleotides and oligopeptides by commercially available machines. Inspired by the success of automated oligosaccharide synthesis through chemical glycosylation, a fully machine-driven automated system is reported here for oligosaccharides synthesis through enzymatic glycosylation in aqueous solution. The designed full automation system is based on the use of a thermosensitive polymer and a commercially available peptide synthesizer. This study represents a proof-of-concept that the enzymatic synthesis of oligosaccharides can be achieved in an automated manner using a commercially available peptide synthesizer.

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Machine‐Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer

et al. 2018

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“…Fluorous solid-phase extraction (FSPE) has been employed to isolate compounds of interest from complex samples in organic chemistry and heterogeneous catalysis for a long time. − It relies on the derivatization of target analytes with compounds bearing highly fluorinated portion (called F-tag) and subsequent separation with the aid of perfluorinated solid phases. The unique ability of fluorinated molecules to recognize other molecules bearing a F-tag is termed “fluorous affinity” or “fluorophilicity”. − Recently, this approach has been extended into many “omics” researches, such as proteomics, − glycomics, − and metabolomics, owning to its better compatibility with mass spectrometry (MS) compared with the classic biotin-tag separation strategy, as the F-tag not only enables the selective enrichment of target analytes but also avoids unexpected dissociation of the MS tag during the MS process.…”

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Fluorous Solid-Phase Extraction Technique Based on Nanographite Fluoride

et al. 2017

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Fluorous solid-phase extraction (FSPE) has been employed to isolate target compounds from complex chemical or biological samples in many research areas. However, the lack of efficient and economical available perfluorinated materials impeded its development. In this study, we present a novel nanographite fluoride-based fluorous solid-phase extraction (GF-FSPE) as a replacement of commercially available cartridge-based FSPE, which showed remarkable selectivity, low LOD, high post enrichment recovery, and large enrichment capacity. To demonstrate the potency of GF-FSPE, it was designed and successfully applied to isolate cysteine-containing peptide subsets from complex protein samples to improve the proteome coverage. Additionally, since graphite fluoride was inexpensive and highly commercialized, this study was expected to promote the popularization of FSPE in both chemical and biological separations as well as encourage the synthesis and broaden the application of highly fluorinated carbon fluoride in material science.

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“…The fluorinated conjugates can easily be released from the solid phase by elution with a fluorophilic solvent or methanol. In the chemical synthesis of oligosaccharides, fluorous tags have been installed at the anomeric position and other positions on the glycosyl acceptors as protecting groups, allowing facile purification of the products by FSPE following glycosylation. Alternatively, fluorous tags have been installed as protecting groups on glycosyl donors to expedite the purification of the products.…”

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confidence: 99%

Water‐Soluble Sulfo‐Fluorous Affinity (SOFA) Tag‐Assisted Enzymatic Synthesis of Oligosaccharides

et al. 2018

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Herein, we report a bifunctional sulfo-fluorous affinity (SOFA) tag-assisted enzymatic synthesis and purification strategy for the facile preparation of bioactive glycans using fluorous solid-phase extraction (FSPE). The incorporation of a sulfonate moiety onto the heavy fluorous tag significantly increases its water solubility, which allows the broad use of the inherently hydrophobic fluorous tag in aqueous buffers. In addition, the SOFA tag contains a photocleavable linker, enabling the easy release of amino-functionalized oligosaccharides by UV irradiation. The SOFA tag was used in the synthesis of both negatively charged and neutral glycans to demonstrate its broad utility as an acceptor toward six different glycosyltransferases, significantly improving the feasibility of the preparation of complex glycans using FSPE. All the reactions were performed in an aqueous buffer, a minimum amount of methanol was used to purify the products, and the SOFA tag was easily recovered after photo-irradiation. Thus, the entire synthetic process is environmentally benign.

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Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

Cited by 16 publications

References 40 publications

Machine‐Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer

Machine‐Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer

Fluorous Solid-Phase Extraction Technique Based on Nanographite Fluoride

Water‐Soluble Sulfo‐Fluorous Affinity (SOFA) Tag‐Assisted Enzymatic Synthesis of Oligosaccharides

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