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通过电化学多糖基化反应从葡糖胺单体合成环状β-1,6-寡糖。

Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation.

作者信息

Rahman Md Azadur, Endo Hirofumi, Yamamoto Takashi, Okushiba Shoma, Sasaki Norihiko, Nokami Toshiki

机构信息

Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan.

Center for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan.

出版信息

Beilstein J Org Chem. 2024 Jun 26;20:1421-1427. doi: 10.3762/bjoc.20.124. eCollection 2024.

DOI:10.3762/bjoc.20.124
PMID:38952959
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11216080/
Abstract

The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisaccharide were obtained using the monomer with a 2-azido-2-deoxy group.

摘要

以硫代糖苷为单体，通过电化学聚糖基化反应合成环状β-1,6-低聚葡糖胺的保护前体。带有2,3-恶唑烷酮保护基的单体仅得到环状二糖。使用带有2-叠氮基-2-脱氧基团的单体可得到三糖以内的环状寡糖。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/315bf8615f18/Beilstein_J_Org_Chem-20-1421-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/a31453974932/Beilstein_J_Org_Chem-20-1421-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/c73f7097c0c6/Beilstein_J_Org_Chem-20-1421-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/4d6304d9b832/Beilstein_J_Org_Chem-20-1421-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/6e039eaf3207/Beilstein_J_Org_Chem-20-1421-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/315bf8615f18/Beilstein_J_Org_Chem-20-1421-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/a31453974932/Beilstein_J_Org_Chem-20-1421-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/c73f7097c0c6/Beilstein_J_Org_Chem-20-1421-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/4d6304d9b832/Beilstein_J_Org_Chem-20-1421-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/6e039eaf3207/Beilstein_J_Org_Chem-20-1421-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed21/11216080/315bf8615f18/Beilstein_J_Org_Chem-20-1421-g006.jpg

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本文引用的文献

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Promoter-Controlled Synthesis and Conformational Analysis of Cyclic Mannosides up to a 32-mer.启动子控制的环状甘露糖苷（长达32聚体）的合成及构象分析
Angew Chem Int Ed Engl. 2023 Oct 23;62(43):e202307851. doi: 10.1002/anie.202307851. Epub 2023 Jul 20.
2
Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides.通过硫代糖苷的电化学多聚糖基化反应合成几丁质寡糖的保护前体。
Beilstein J Org Chem. 2022 Aug 30;18:1133-1139. doi: 10.3762/bjoc.18.117. eCollection 2022.
3
Synthesis of cyclic α-1,4-oligo--acetylglucosamine 'cyclokasaodorin' a one-pot electrochemical polyglycosylation-isomerization-cyclization process.
循环α-1,4-寡--乙酰氨基葡萄糖“环卡沙多林”的一锅电化学多聚糖化-异构化-环化合成。
Chem Commun (Camb). 2022 Jul 14;58(57):7948-7951. doi: 10.1039/d2cc02287g.
4
Electrochemical Assembly for Synthesis of Middle-Sized Organic Molecules.电化学组装用于合成中尺度有机分子。
Chem Rec. 2021 Sep;21(9):2389-2396. doi: 10.1002/tcr.202100085. Epub 2021 Jun 8.
5
Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides.电化学糖基化作为立体选择性合成环状寡糖的一种辅助工具。
ChemistryOpen. 2019 Jul 3;8(7):869-872. doi: 10.1002/open.201900185. eCollection 2019 Jul.
6
Conformationally supple glucose monomers enable synthesis of the smallest cyclodextrins.构象灵活的葡萄糖单体可用于最小环糊精的合成。
Science. 2019 May 17;364(6441):674-677. doi: 10.1126/science.aaw3053. Epub 2019 Apr 11.
7
Synthesis and Structure of Cyclic Trisaccharide with Expanded Glycosidic Linkages.具有扩展糖苷键的环状三糖的合成与结构。
J Org Chem. 2016 Jun 3;81(11):4616-22. doi: 10.1021/acs.joc.6b00462. Epub 2016 May 24.
8
Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides.通过硫糖苷的电化学迭代组装自动化进行寡糖的溶液相合成。
Org Lett. 2013 Sep 6;15(17):4520-3. doi: 10.1021/ol402034g. Epub 2013 Aug 15.
9
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Beilstein J Org Chem. 2012;8:456-60. doi: 10.3762/bjoc.8.52. Epub 2012 Mar 28.
10
Electrochemistry of conducting polymers--persistent models and new concepts.导电聚合物的电化学——持久模型与新概念
Chem Rev. 2010 Aug 11;110(8):4724-71. doi: 10.1021/cr900226k.