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N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的碳水化合物类似物(位置、构型和旋光)的合成及其免疫佐剂活性。

Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.

作者信息

Hasegawa A, Kaneda Y, Goh Y, Nishibori K, Kiso M, Azuma I

出版信息

Carbohydr Res. 1981 Aug 1;94(2):143-63. doi: 10.1016/s0008-6215(00)80713-2.

Abstract

2-Acetamido-2-deoxy-4- and -6-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose, 2-acetamido-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-allopyranose, -D-gulopyranose, -D-galactopyranose, -D-mannopyranose, and -L-idopyranose, and 3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.

摘要

合成了2-乙酰氨基-2-脱氧-4-和-6-O-(D-2-丙酰基-L-丙氨酰-D-异谷氨酰胺)-D-吡喃葡萄糖、2-乙酰氨基-2-脱氧-3-O-(D-2-丙酰基-L-丙氨酰-D-异谷氨酰胺)-D-阿洛吡喃糖、-D-古洛吡喃糖、-D-半乳吡喃糖、-D-甘露吡喃糖和-L-艾杜吡喃糖,以及3-O-(D-2-丙酰基-L-丙氨酰-D-异谷氨酰胺)-D-和-L-吡喃葡萄糖,以阐明N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺中碳水化合物部分免疫佐剂活性的结构要求。在豚鼠中检测了N-乙酰胞壁酰二肽类似物的免疫佐剂活性。

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