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  • Title: Chemical modification of the C-6 substituent in the carbohydrate moiety of N-acetylmuramoyl-L-alanyl-D-isoglutamine (MDP), and the immunoadjuvant activity.
    Author: Okumura H, Tokushima Y, Saiki I, Azuma I, Kiso M, Hasegawa A.
    Journal: Carbohydr Res; 1983 Oct 14; 122(1):87-98. PubMed ID: 6652634.
    Abstract:
    N-Acetyl-6-O-mesyl-, -6-O-methyl-, and -4,6-di-O-methyl-muramoyl-L-alanyl-D-isoglutamine and N-acetyl-6-chloro-, -6-bromo-, and -6-azido-6-deoxymuramoyl-L-alanyl-D-isoglutamine were synthesized from benzyl 2-acetamido-2-deoxy-3-O-[D-1-(methoxycarbonyl) ethyl]-alpha-D-glucopyranoside and its 6-O-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-acetylmuramoyl-L-alanyl-D-isoglutamine.
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