A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

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Abstract

A highly efficient and stereoselective approach to the synthesis of biologically important and complex α-glycosyl phosphosaccharides (GPSs) has been disclosed, employing direct gold(I)-catalyzed glycosylation of the weakly nucleophilic phosphoric acid acceptors. The broad substrate scope is demonstrated with more than 45 examples, including glucose (Glc), xylose, glucouronatose, galactose (Gal), mannose (Man), rhamnose (Rha), fucose (Fuc), 2-N3-2-dexoxymannose (ManN3), 2-N3-2-dexoxyglucose (GlcN3), 2-N3-2-dexoxygalactose (GalN3) and unnatural carbohydrates. Moreover, the glycosyl phosphotriester prepared herein was successfully applied to the one-pot synthesis of a GPS from Leishmania donovani, and an effective preparation of a trisaccharide diphosphate of GPS fragments from Hansenula capsulate via iterative elongation strategy is realized.
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A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Article A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides Yugen Zhu, Xiaojuan Zhang, Yutong Yang, Jiahao Ding, Yun Zhao, and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-669845/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 20 Jan, 2022 Read the published version in Nature Communications → Version 1 posted You are reading this latest preprint version Abstract A highly efficient and stereoselective approach to the synthesis of biologically important and complex α-glycosyl phosphosaccharides (GPSs) has been disclosed, employing direct gold(I)-catalyzed glycosylation of the weakly nucleophilic phosphoric acid acceptors. The broad substrate scope is demonstrated with more than 45 examples, including glucose (Glc), xylose, glucouronatose, galactose (Gal), mannose (Man), rhamnose (Rha), fucose (Fuc), 2-N3-2-dexoxymannose (ManN3), 2-N3-2-dexoxyglucose (GlcN3), 2-N3-2-dexoxygalactose (GalN3) and unnatural carbohydrates. Moreover, the glycosyl phosphotriester prepared herein was successfully applied to the one-pot synthesis of a GPS from Leishmania donovani, and an effective preparation of a trisaccharide diphosphate of GPS fragments from Hansenula capsulate via iterative elongation strategy is realized. Inorganic Chemistry General Biochemistry Applied Biochemistry α-glycosyl phosphosaccharides (GPSs) synthesis Full Text Additional Declarations There is NO Competing Interest. Supplementary Files SI1ProcedureandCharacterization.pdf SI-1 Procedure and characterization SI2NMRSpectra.pdf SI-2 NMR spectra Cite Share Download PDF Status: Published Journal Publication published 20 Jan, 2022 Read the published version in Nature Communications → Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. 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