Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate

A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthe...

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Autores principales: Nagata, Sakuto, Tomida, Hirotaka, Iwai-Hirose, Haruka, Tanaka, Hide-Nori, Ando, Hiromune, Imamura, Akihiro, Ishida, Hideharu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071174/
https://www.ncbi.nlm.nih.gov/pubmed/35530445
http://dx.doi.org/10.1039/c9ra05797h
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author Nagata, Sakuto
Tomida, Hirotaka
Iwai-Hirose, Haruka
Tanaka, Hide-Nori
Ando, Hiromune
Imamura, Akihiro
Ishida, Hideharu
author_facet Nagata, Sakuto
Tomida, Hirotaka
Iwai-Hirose, Haruka
Tanaka, Hide-Nori
Ando, Hiromune
Imamura, Akihiro
Ishida, Hideharu
author_sort Nagata, Sakuto
collection PubMed
description A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase.
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spelling pubmed-90711742022-05-06 Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate Nagata, Sakuto Tomida, Hirotaka Iwai-Hirose, Haruka Tanaka, Hide-Nori Ando, Hiromune Imamura, Akihiro Ishida, Hideharu RSC Adv Chemistry A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase. The Royal Society of Chemistry 2019-09-09 /pmc/articles/PMC9071174/ /pubmed/35530445 http://dx.doi.org/10.1039/c9ra05797h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Nagata, Sakuto
Tomida, Hirotaka
Iwai-Hirose, Haruka
Tanaka, Hide-Nori
Ando, Hiromune
Imamura, Akihiro
Ishida, Hideharu
Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title_full Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title_fullStr Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title_full_unstemmed Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title_short Synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
title_sort synthesis of a 1,2-cis-indoxyl galactoside as a chromogenic glycosidase substrate
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071174/
https://www.ncbi.nlm.nih.gov/pubmed/35530445
http://dx.doi.org/10.1039/c9ra05797h
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