Synthesis of Lacto‐ and Neolacto‐series Ganglioside Analogs Containing N‐Glycolylneuraminic Acid: Probes for Investigation of Specific Receptor Structures Recognized by Influenza A Viruses

Abstract

Sialic acids are essential components of host‐cell surface receptors for infection of influenza virus. To investigate the specific receptor structures recognized by various influenza A viruses, a series of lacto‐ and neolacto‐series ganglioside analogs containing N‐glycolylneuraminic acid (Neu5Gc) have been synthesized. The pentasaccharide structures of Neu5Gc‐α‐(2→3)/(2→6)‐lactotetraose (IV³⁽⁶⁾Neu5GcLcOse) and Neu5Gc‐α‐(2→3)/(2→6)‐neolactotetraose (IV³⁽⁶⁾Neu5GcnLcOse) were constructed by glycosylation of the suitably protected trisaccharide acceptors (2A and 2B) with the Neu5Gc‐α‐(2→3)/(2→6)‐Gal trichloroacetimidate donors (1 and 21), respectively. Transformation of the 2‐(trimethylsilyl)ethyl group at the reducing end in 4, 11, 23, and 30 into the trichloroacetimidate group gave a series of Neu5Gc‐α‐(2→3)/(2→6)‐lacto‐ and neolactotetraose donors (7, 13, 26, and 33), which were coupled with 2‐(tetradecyl)hexadecanol (8), to give the corresponding glycolipids (9, 14, 27, and 34). Finally, the complete removal of the O‐acyl groups and saponification of the methyl ester group gave the desired ganglioside analogs (10, 15, 28, and 35).

^#Synthetic studies on sialoglycoconjugates, Part 129. For Part 128, see Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res., 2003, 338, 503–514.

Keywords:

• Sialic acid
• Ganglioside
• Influenza
• Glycosylation
• Carbohydrate

Acknowledgment

This work was supported in part by a Grant‐in‐Aid (No. 12306007) for Scientific Research from Japan Society for the Promotion of Science.

Notes

^#Synthetic studies on sialoglycoconjugates, Part 129. For Part 128, see Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res., 2003, 338, 503–514.