ArticleInternational journal of molecular sciences2021
Indolyl Septanoside Synthesis for In Vivo Screening of Bacterial Septanoside Hydrolases.
Article in International journal of molecular sciences, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 5 citations in OpenAlex.
- Unnatural C6-Substituted d-Galactosides as Attenuated Substrates of Glycosyl Hydrolases.Chembiochem : a European journal of chemical biology · 2026Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- Does size matter? - Comparing pyranoses with septanoses as ligands of the bacterial lectin FimH.European journal of medicinal chemistry · 2024Article
- Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.Journal of the American Chemical Society · 2023Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
Abstract
Building-up and breaking-down of carbohydrates are processes common to all forms of life. Glycoside hydrolases are a broad class of enzymes that play a central role in the cleavage of glycosidic bonds, which is fundamental to carbohydrate degradation. The large majority of substrates are five- and six-membered ring glycosides. Our interest in seven-membered ring septanose sugars has inspired the development of a way to search for septanoside hydrolase activity. Described here is a strategy for the discovery of septanoside hydrolases that uses synthetic indolyl septanosides as chromogenic substrates. Access to these tool compounds was enabled by a route where septanosyl halides act as glycosyl donors for the synthesis of the indolyl septanosides. The screening strategy leverages the known dimerization of 3-hydroxy-indoles to make colored dyes, as occurs when the β-galactosidase substrate X-Gal is hydrolyzed. Because screens in bacterial cells would enable searches in organisms that utilize heptoses or from metagenomics libraries, we also demonstrate that septanosides are capable of entering
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Registered trials
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