{"id":65786,"date":"2024-06-19T23:59:07","date_gmt":"2024-06-19T15:59:07","guid":{"rendered":"https:\/\/www.science.nus.edu.sg\/?p=65786"},"modified":"2024-06-20T08:57:41","modified_gmt":"2024-06-20T00:57:41","slug":"direct-transformation-of-native-sugars-into-complex-glycosides-using-biomimetic-chemistry","status":"publish","type":"post","link":"https:\/\/www.science.nus.edu.sg\/blog\/2024\/06\/direct-transformation-of-native-sugars-into-complex-glycosides-using-biomimetic-chemistry\/","title":{"rendered":"Boosting the synthesis of stable sugar compounds with a novel nature-inspired approach"},"content":{"rendered":"<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">Researchers from the National University of Singapore (NUS) have developed a new biomimetic concept to convert naturally occurring sugars into diverse classes of stable glycosides and glycoproteins without using protecting-group chemistry. This innovation promises to accelerate carbohydrate synthesis and post-translational protein modification, with potential applications for the pharmaceutical, cosmetic and biotechnology sectors.<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">The research team was led by Associate Professor KOH Ming Joo from the NUS Department of Chemistry, in collaboration with Professor Benjamin G. DAVIS from the Rosalind Franklin Institute and the University of Oxford, United Kingdom. Their research breakthrough was published in the prestigious scientific journal <a href=\"https:\/\/www.nature.com\/articles\/s41586-024-07548-0\"><i>Nature<\/i><\/a> on 19 June 2024.<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">Carbohydrates play indispensable roles in biological processes, and the simple attachment of a glycosyl moiety often adds desirable functions. Due to their importance, considerable efforts have been devoted to synthesising these carbohydrates and their derivatives to better understand their properties and functions, as well as to develop sugar-based drugs, skincare ingredients and other valuable products. In particular, <span style=\"font-style: normal !msorm;\"><i>C<\/i><\/span>-glycosyl compounds have gained prominence as metabolically stable and often more biologically potent mimics of <span style=\"font-style: normal !msorm;\"><i>O<\/i><\/span>-glycosides. <\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">However, the chemical synthesis of <span style=\"font-style: normal !msorm;\"><i>C<\/i><\/span>-glycosyl compounds has traditionally been plagued by the need for multi-step protecting-group strategies and harsh conditions, which generate excessive waste. This is because native sugars contain multiple hydroxyl groups of similar reactivity, making it difficult to selectively react with them without using protecting groups. For many years, the practical inefficiencies of these approaches have limited their use in synthetic glycochemistry and in conditions requiring high biocompatibility. <\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">Prof Koh said, \u201cMany research groups, including ours, have endeavoured tirelessly to conceive a protecting-group-free chemical glycosylation approach that can directly transform native sugars into the desired glycosides by selective functionalisation at the anomeric position. However, this has proven to be extremely challenging.\u201d<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><b><u><span lang=\"EN-GB\">Nature-inspired \u2018cap and glycosylate\u2019 technology<\/span><\/u><\/b><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">Enzymes known as glycosyltransferases are highly proficient in mediating site-selective glycosylations at the anomeric carbon without having to protect the remaining hydroxyl groups. The researchers took a page from nature by designing a biomimetic chemical approach that preferentially activates and substitutes the anomeric hydroxyl group in a native sugar with a nucleophilic thiol <ins cite=\"mailto:Koh%20Ming%20Joo\" datetime=\"2024-06-18T17:15\">(<\/ins>process referred to caping). This generates a temporary thioglycoside intermediate that, under photoinduced conditions, undergoes stereocontrolled desulfurative cross-coupling with a suitable reagent (process referred to as glycosylation). Similar to nature, this &#8216;cap and glycosylate\u2019 strategy converts native sugars into glycosides in a single operation.<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">To demonstrate the broad applicability of this technology, the researchers synthesised densely functionalised <span style=\"font-style: normal !msorm;\"><i>C<\/i><\/span>-glycosyl, <span style=\"font-style: normal !msorm;\"><i>S<\/i><\/span>-glycosyl, <span style=\"font-style: normal !msorm;\"><i>Se<\/i><\/span>-glycosyl and <span style=\"font-style: normal !msorm;\"><i>O<\/i><\/span>-glycosyl compounds. Beyond small-molecule glycosylation, the method can be extended to complex biomolecules. Previously, post-translational chemical glycosylation of proteins by direct anomeric functionalisation of native sugars was challenging and largely unexplored. In the new work, <span style=\"font-style: normal !msorm;\"><i>C<\/i><\/span>-glycosylation of four proteins of different sizes and folds was successfully achieved, underscoring the power of the \u2018cap and glycosylate\u2019 approach.<\/span><\/span><\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" width=\"810\" height=\"448\" src=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_2.jpg\" alt=\"\" class=\"alignnone size-full wp-image-65525\" srcset=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_2.jpg 810w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_2-300x166.jpg 300w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_2-768x425.jpg 768w\" sizes=\"(max-width: 810px) 100vw, 810px\" \/><\/p>\n<p><em><span style=\"font-family: arial, helvetica, sans-serif; font-size: 14px;\"><span lang=\"EN-GB\">Glycosylation reaction setup using a photoreactor of 460<\/span><span lang=\"EN-GB\">&#8211;<\/span><span lang=\"EN-GB\">470 nm wavelength (blue light). Chemical ingredients were typically added into reaction vials, sealed and allowed to vigorously stir at room temperature under 12 W blue light illumination for 24 hours. [Credit: Nature]<\/span><\/span><\/em><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">Prof Davis said, \u201cOur group has spent a number of years exploring the idea of inserting information into biological molecules such as proteins and sugars to alter their function. One of the things that we have found is that carbon-centred radicals are wonderfully useful yet benign reactive intermediates for achieving new chemistries in biological systems. In this research, by generating free glycosyl radicals as intermediates directly from native sugars we are trying to mimic what is happening in biology to make the synthesis of these glycosides and glycoproteins far more efficient. This efficient \u2018harvesting\u2019 of native sugars that can be plugged directly into new glycoconjugates has the potential to open up a number of different avenues including the development of diverse sugar-based therapeutics.\u201d<\/span><\/span><\/p>\n<p><img decoding=\"async\" width=\"536\" height=\"323\" src=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_4.jpg\" alt=\"\" class=\"alignnone size-full wp-image-65785\" srcset=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_4.jpg 536w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2024\/06\/382._Koh_MJ_CHM_20240610_4-300x181.jpg 300w\" sizes=\"(max-width: 536px) 100vw, 536px\" \/><\/p>\n<p><em><span lang=\"EN-GB\" style=\"font-family: arial, helvetica, sans-serif; font-size: 14px;\">Assoc Prof Koh Ming Joo led the research team, in collaboration with the Rosalind Franklin Institute and the University of Oxford, to develop a novel method to synthesise stable sugar compounds which have potential applications for the pharmaceutical, cosmetic and biotechnology sectors.<\/span><\/em><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><span lang=\"EN-GB\">\u201cWe believe that this biomimetic \u2018cap and glycosylate\u2019 technology would pave the way towards modernising carbohydrate and glycoconjugate synthesis without the need for protecting-groups. This would bring enormous benefits in saving costs, time and manpower, empowering researchers to rapidly access saccharides and offering a practical platform to introduce fully unprotected glycosyl groups into biological systems,\u201d added Prof Koh.<\/span><\/span><\/p>\n<p>&nbsp;<\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\"><strong>Reference<\/strong><\/span><\/p>\n<p><span lang=\"EN-GB\" style=\"font-family: arial, helvetica, sans-serif; font-size: 16px;\">Jiang Y; Wei Y; Zhou Q; Sun G; Fu X; Levin N; Zhang Y; Liu, W; Song, N; Mohammed, S; Davis BG*; Koh MJ*, \u201cDirect radical functionalization of native sugars\u201d Nature DOI: <a href=\"https:\/\/www.nature.com\/articles\/s41586-024-07548-0\">10.1038\/s41586-024-07548-0<\/a> Published: 2024.<\/span><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Researchers from the National University of Singapore (NUS) have developed a new biomimetic concept to convert naturally occurring sugars into&#8230;<\/p>\n","protected":false},"author":16,"featured_media":65523,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[11185,13],"tags":[],"class_list":["post-65786","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-carbohydrate-chemistry","category-research-news"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v23.6 (Yoast SEO v23.6) - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Boosting the synthesis of stable sugar compounds with a novel nature-inspired approach - NUS Faculty of Science<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" 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