Chemical modification of the C-6 substituent in the carbohydrate moiety of N-acetylmuramoyl-l-alanyl-d-isoglutamine (MDP), and the immunoadjuvant activity

✍ Scribed by Hiroyuki Okumura; Yasuo Tokushima; Ikuo Saiki; Ichiro Azuma; Makoto Kiso; Akira Hasegawa

• Book ID: 102992249
• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 687 KB
• Volume: 122
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88409-2

✦ Synopsis

N-Acetyl-6-0-mesyl-, -6-O-methyl-, and -4,6-di-O-methyl-muramoyl-Lalanyl-D-isoglutamine and N-acetyl-6-chloro-, -6-bromo-, and -6-azido-6deoxymuramoyl-L-alanyl-D-isoglutamine were synthesized from benzyl 2acetamido-2-deoxy-3-0-[D-l-(methoxycarbonyl)ethyl]-a-D-glucopyranoside and its 6-0-mesyl derivative.

The immunoadjuvant activity of the products was examined, in order to clarify the structural requirements for the activity of the carbohydrate moiety in N-acetylmuramoyI-L-alanyl-D-isoglutamine.