Recent advances in photoinduced glycosylation: oligosaccharides, glycoconjugates and their synthetic applications

Abstract

Carbohydrates have been demonstrated to perform imperative act in biological processes. This review highlights recent uses of photoinduced glycosylation in carbohydrate chemistry for the synthesis of oligosaccharides, thiosugars, glycoconjugates and glycoprotein.

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

“…We also included commercially available eosin Y ( C ) in our studies of this ArOH‐type photoacid catalysis. We herein describe these studies, which led to the development of a direct, visible‐light‐induced photoactivation method for the catalytic stereoselective conversion of glycals into 2‐deoxyglycosides.…”

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

“…The two acetonide protecting groups were removed under acidic condition using Dowex H + resin in aqueous THF to obtain C- In the 1 H-NMR (500 MHz, CDCl 3 ) spectrum of 5, the anomeric proton appeared as a doublet at 4.52 ppm with a coupling constant of 9.0 Hz, confirming the β-linkage. The formation of the compound was further confirmed by 1 H-1 H COSY, 13 C-NMR and ESI-MS HRMS spectral data. The methodology of synthesising 1,3-difunctionalized glycoconjugates was further extended to the preparation of other glycoconjugates, such as the α-linked C-3 O-propargylated glycolipid.…”

“…8,9 The presence of a multiple number of chiral centres and the different relative orientation of the hydroxyl groups with respect to each other make carbohydrates a source of chiral backbones that can easily be diversely functionalized with the help of selective protection and deprotection methods. [10][11][12][13] Carbohydrates are frequently used for the synthesis of various structurally diverse biomolecules, such as multivalent compounds and glycoamino acid mimics. Compared to monofunctionalized glycoconjugates, multifunctionalized glycoconjugates with different functional groups in the same sugar moiety have a better binding affinity with various bacteria, virus or lectins.…”

Recent Developments in Stereoselective Chemical Glycosylation

“…Chemists have long utilized ultraviolet (UV) light irradiation to perform glycosylation. The light energy either cleaves the aglycone directly to activate the donor, or is harvested by a photosensitizer for further activation …”