Fig. 3: Chemoenzymatic syntheses of O-acetylated sialosides. | Nature Chemistry

Fig. 3: Chemoenzymatic syntheses of O-acetylated sialosides.

From: Synthetic O-acetylated sialosides facilitate functional receptor identification for human respiratory viruses

Fig. 3

a, Chemical synthesis of 1a. See Supplementary Fig. 4 for details on the regioselective C-8-to-C-9 acetyl ester migration performed on deprotected oligosaccharides in DMSO. b, Modifications of 1a and 2a using HE-catalysed O-acetyl removal and base-mediated O-acetyl migration. Enzymatic reactions went to full conversion. Representative yields in parentheses were determined post-HPLC purification. 7-O-acetyl remained stable (for sialoforms 1b, 2b, 1d, 2d, 1f and 2f) during the course of reaction and purification. See Supplementary Figs. 5–8 and Supplementary Table 2 for the structural confirmation. c, Chemical synthesis and enzymatic modification of 3a using HEs. MHV-S HE removed 4-O-acetyl groups of both the non-reducing and reducing end Neu5Ac residues. Lc, 6-aminocaproic acid linker; NBI, 5-norbornene-2,3-dicarboxylic acid imido; Su, succinimido.

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