Chemoenzymatic Synthesis of < em > N < /em > -Acetyl Analogues of 9- < em > O < /em > -Acetylated b-Series Gangliosides

Tetrahedron. 2023 Aug 3;142:133522. doi: 10.1016/j.tet.2023.133522. Epub 2023 Jun 15.ABSTRACTThe stable N-acetyl analogues of biologically important 9-O-acetylated b-series gangliosides including 9NAc-GD3, 9NAc-GD2, 9NAc-GD1b, and 9NAc-GT1b were chemoenzymatically synthesized from a GM3 sphingosine. Two chemoenzymatic methods using either 6-azido-6-deoxy-N-acetylmannosamine (ManNAc6N3) as a chemoenzymatic synthon or 6-acetamido-6-deoxy-N-acetylmannosamine (ManNAc6NAc) as an enzymatic precursor for 9-acetamido-9-deoxy-N-acetylneuraminic acid (Neu5Ac9NAc) were developed and compared for the synthesis of 9NAc-GD3. The latter method was found to be more efficient and was used to produce the desired 9-N-acetylated glycosylsphingosines. Furthermore, glycosylsphingosine acylation reaction conditions were improved to obtain target 9-N-acetylated gangliosides in a faster reaction with an easier purification process compared to the previous acylation conditions.PMID:37981995 | PMC:PMC10653377 | DOI:10.1016/j.tet.2023.133522

Source: Tetrahedron - November 20, 2023 Category: Chemistry Authors: Hai Yu Zimin Zheng Libo Zhang Xiaohong Yang Ajit Varki Xi Chen Source Type: research