title: Synthesis of a suite of click-compatible sugar analogs for probing carbohydrate metabolism.
abstract: Metabolic labeling based on the click chemistry between alkynyl and azido groups offers a powerful tool to study the function of carbohydrates in living systems, including plants. Herein, we describe the chemical synthesis of six alkynyl-modified sugars designed as analogs to D-glucose, D-mannose, L-rhamnose and sucrose present in plant cell walls. Among these new alkynyl probes, four of them are the 6-deoxy-alkynyl analogs of the corresponding sugars and do not possess any 6-OH groups. The other two are based on a new structural design, in which an ethynyl group is incorporated at the C-6 position of the sugar and the 6-OH group remains. The synthetic routes for both types of probes share common aldehyde intermediates, which are derived from the corresponding 6-OH precursor with other hydroxy groups protected. The overall synthesis sequence of these probes is efficient, concise, and scalable.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA; Center for Lignocellulose Structure and Formation, The Pennsylvania State University, University Park, PA 16802, USA.
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.affiliation: Department of Biology, The Pennsylvania State University, University Park, PA 16802, USA; Center for Lignocellulose Structure and Formation, The Pennsylvania State University, University Park, PA 16802, USA.
authors.forename: Daniel D
authors.initials: DD
authors.lastname: McClosky
authors.affiliation: Department of Biology, The Pennsylvania State University, University Park, PA 16802, USA; Center for Lignocellulose Structure and Formation, The Pennsylvania State University, University Park, PA 16802, USA. Electronic address: cta3@psu.edu.
authors.forename: Charles T
authors.initials: CT
authors.lastname: Anderson
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA; Center for Lignocellulose Structure and Formation, The Pennsylvania State University, University Park, PA 16802, USA; State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China. Electronic address: guc11@psu.edu.
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D050260:Carbohydrate Metabolism; D057930:Click Chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives*; D005947:Glucose / Q000031:analogs & derivatives; D008358:Mannose / Q000031:analogs & derivatives; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012210:Rhamnose / Q000031:analogs & derivatives; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D009005:Monosaccharides; D013395:Sucrose; D003847:Deoxyglucose; D005947:Glucose; D008358:Mannose; D012210:Rhamnose
keywords: Carbohydrate metabolism; Click chemistry; Labeling probe