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Reversible photocontrol of glycosides and glycoconjugates structures is a very attractive approach to modulate, in a spatiotemporal way, the various properties and biological activities of carbohydrates. We have synthesized three new azobenzene-derived glycomacrolactones from thioglycopyranosides. The synthesized cyclic glycoazobenzenes can be reversibly photoisomerized between E and Z isomers with high fatigue resistance. A 1H NMR spectroscopic study shows that E ? Z isomerization of glycomacrocycles induces large conformational change of the macrocyclic structures, without changing sugar 4C1 chair conformation. The Z-glycoazobenzenes can be thermally converted back to the E-isomers. Interestingly, these 16 to 17-membered Z-glycomacrolactones display higher thermal stability than the reported macrocyclic azobenzenes, the half-life varying from 37 to 72 days. The excellent photoswitching property and bistability of the synthesized glycoazobenzenes open a new opportunity for the convergent synthesis of diastereomers of glycomacrocycles. Furthermore, chiroptical properties have been observed for both E and Z glycomacrolactones. The geometry of different isomers of macrocycles has been optimized with DFT calculations. Theoretical CD spectra obtained by TD-DFT suggest that the E and Z glycomacrocycles adopt preferentially (P) helical structure for the azobenzene moiety.
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Reference：
Chiral Catalysts,
Chiral catalysts – SlideShare