Synthesis of N-acetyl-4,8-dideoxyneuraminic acid-containing ganglioside GM3

✍ Scribed by Masahiro Yoshida; Hideharu Ishida; Makoto Kiso; Akira Hasegawa

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 476 KB
• Volume: 280
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00327-4

✦ Synopsis

Ganglioside GM 3, as well as other gangliosides, offers a variety of modifications in its sialic acid and ceramide moieties GM 3 exhibits various types of important biological activities such as an influenza A virus receptor [2,3], an inducer [4] of monocytic differentiation of human myeloid, an enhancer or inhibitor of protein kinase activity [5],

an immunosuppressant [6,7], and a substrate for Trypanosoma cruzi trans-sialidase [8].

In view of these facts, it is of interest to clarify the functions of GM 3 at the molecular level. Previously [9], we have synthesized GM3, analogues containing a variety of lipophilic parts in place of ceramide, as well as analogues with modified sialic acids, in order to elucidate the role of the ceramide and sialic acid parts in the function of GM 3. In continuing to investigate the structure-activity relationships of gangliosides, we describe herein the synthesis of N-acetyl-4,8-dideoxyneuraminic acid-containing GM 3.