Click Reaction in Carbohydrate Chemistry: Recent Developments and Future Perspective+

The Identification of Perillyl Alcohol Glycosides with Improved Antiproliferative Activity

“…The scope of sugars selected for this study included representative pentoses ( d/l -arabinose, PG3 / PG28 ; l -ribose, PG17 ; d -xylose, PG22 ), hexoses ( d/l -glucose, PG1 / PG6 ; 3- O -methyl- d -glucose, PG4 ; l -rhamnose, PG32 ), azidosugars (6-deoxy-6-azido- d -glucose, PG2 ; 3-deoxy-3-azido- d -glucose, PG8 ; 4-deoxy-4-azido- d -glucose, PG9 ; 2-deoxy-2-azido- d -glucose, PG13 ; 4,6-deoxy-4,6-diazido- d -glucose, PG20 , 4-deoxy-4-azido- l -glucose, PG24 ; 4-deoxy-4-azido- d -xylose, PG34 ), fluorosugars (3-deoxy-3-fluoro- d -glucose, PG18 ; 4-deoxy-4-fluoro- d -glucose, PG21 ; 2-deoxy-2-fluoro- d -glucose, PG29 ; 2-deoxy-2-fluoro- d -mannose, PG30 ) N -acyl sugars ( N -acetyl- d -galactosamine, PG5 ; N -acetylmuramic acid, PG12 ; streptozocin, PG16 ; 3- N -decanoyl- d -glucosamine, PG23 ; 6- N -decanoyl- d -glucos amine, PG26 ; 3- N -allyloxylcarbonyl- d -glucosamine, PG27 ; 2- N -allyloxylcarbonyl- d -glucosamine, PG31 ; 6- N -allyloxylcarbonyl- d -glucosamine, PG33 ), an acid-bearing sugar ( d -glucuronic acid, PG25 ), and a dissacharide ( d -cellobiose, PG14 ) with a bias toward glucosides and acyl glucosides based upon the previously reported active glycosides ( 1a and 3a ). The inclusion of azidosugars served as a starting point for subsequent divergence via chemoselective modification [via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition] 35,36 or selective reduction to afford the corresponding aminosugar conjugates (Scheme 2). 30,32,37−39 A library of 34 distinct neoglycosides ( PG1 – PG34 ) were synthesized (Figure S1 and Table S1 in Supporting Information) in good to excellent yields (23–82%), with the β-anomer as predominate product in most cases, consistent with previous studies.…”

Click Inspired Synthesis of 1,2,3‐Triazole‐linked 1,3,4‐Oxadiazole Glycoconjugates

“…1,3,4‐Oxadiazoles linked to sugar skeleton such as a glucofuranose, glucopyranose, xylopyranose, psicopyranose, thioglycosides and fructopyranose are documented in literature, and many of these derivatives have showed potential antibacterial, anticancer, antitumor, and antidiabetic activity . Considering the aforementioned facts and our previous experience on click‐mediated development of glycoconjugates of diverse application , we intend to conjugate the orthogonally protected saccharide residue with biologically privileged 1,3,4‐oxadiazole framework using Cu(I)‐catalyzed click reaction to obtain glycohybrids, which may exhibit the medicinal properties of both the parent components. Herein, we report a straightforward synthesis of 1,2,3‐triazole linked 1,3,4‐oxadiazole‐sugar derivatives by click reaction of an azide armed 1,3,4‐oxadiazole entity with diverse set of terminal glycosyl alkynes under mild reaction condition.…”

Fluorogenic dual click derived bis-glycoconjugated triazolocoumarins for selective recognition of Cu(II) ion

“…20 In particular, the carbohydrate based chemosensors have attracted considerable interest as sugars are abundant and low cost starting materials with structural and configurational diversity. 13 In literature, very few sugar-based fluorescent probes have been reported for selective detection of metal ions. 21-27 Therefore, in continuation of our ongoing research on the development of glycoconjugates for diverse applications, 28-32 we envisaged to design a chemosensor by incorporating triazolocoumarin skeletons to the sugar molecules via fluorogenic dual click reaction.…”