Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, thr...

Full description

Bibliographic Details
Main Authors: Yuta Isoda, Norihiko Sasaki, Kei Kitamura, Shuji Takahashi, Sujit Manmode, Naoko Takeda-Okuda, Jun-ichi Tamura, Toshiki Nokami, Toshiyuki Itoh
Format: Article
Language:English
Published: Beilstein-Institut 2017-05-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
automated synthesis
electrochemical oxidation
glycosylation
glucosamine
total synthesis
Online Access:https://doi.org/10.3762/bjoc.13.93
id doaj-c6589f25bada4ab08a330b2166548f59
record_format Article
spelling doaj-c6589f25bada4ab08a330b2166548f592021-02-02T01:36:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-05-0113191992410.3762/bjoc.13.931860-5397-13-93Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building blockYuta Isoda0Norihiko Sasaki1Kei Kitamura2Shuji Takahashi3Sujit Manmode4Naoko Takeda-Okuda5Jun-ichi Tamura6Toshiki Nokami7Toshiyuki Itoh8Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Regional Environment, Faculty of Regional Sciences, Tottori University, 4-101 Koyama-minami, Tottori 680-8551, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanDepartment of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanThe total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.https://doi.org/10.3762/bjoc.13.93automated synthesiselectrochemical oxidationglycosylationglucosaminetotal synthesis
collection DOAJ
language English
format Article
sources DOAJ
author Yuta Isoda
Norihiko Sasaki
Kei Kitamura
Shuji Takahashi
Sujit Manmode
Naoko Takeda-Okuda
Jun-ichi Tamura
Toshiki Nokami
Toshiyuki Itoh
spellingShingle Yuta Isoda
Norihiko Sasaki
Kei Kitamura
Shuji Takahashi
Sujit Manmode
Naoko Takeda-Okuda
Jun-ichi Tamura
Toshiki Nokami
Toshiyuki Itoh
Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
Beilstein Journal of Organic Chemistry
automated synthesis
electrochemical oxidation
glycosylation
glucosamine
total synthesis
author_facet Yuta Isoda
Norihiko Sasaki
Kei Kitamura
Shuji Takahashi
Sujit Manmode
Naoko Takeda-Okuda
Jun-ichi Tamura
Toshiki Nokami
Toshiyuki Itoh
author_sort Yuta Isoda
title Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
title_short Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
title_full Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
title_fullStr Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
title_full_unstemmed Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
title_sort total synthesis of tmg-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2017-05-01
description The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.
topic automated synthesis
electrochemical oxidation
glycosylation
glucosamine
total synthesis
url https://doi.org/10.3762/bjoc.13.93
work_keys_str_mv AT yutaisoda totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT norihikosasaki totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT keikitamura totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT shujitakahashi totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT sujitmanmode totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT naokotakedaokuda totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT junichitamura totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT toshikinokami totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
AT toshiyukiitoh totalsynthesisoftmgchitotriomycinbasedonanautomatedelectrochemicalassemblyofadisaccharidebuildingblock
_version_ 1724311535457665024

Similar Items