Abe Y, Nakagawa S, Naito T, Kawaguchi H
J Antibiot (Tokyo). 1981 Nov;34(11):1434-46. doi: 10.7164/antibiotics.34.1434.
6-O-(3-Amino-3-deoxy-alpha-d-glucopyranosyl)apramycin (17) was prepared by glycosidation of a suitably blocked 5,6-dihydroxy derivative (11) of apramycin with a blocked 3-aminoglucosyl chloride (15). Ribosylation of the 5-hydroxy-6-O-tetrahydropyranyl (THP) derivative (19) of apramycin gave 5-O-(beta-d-ribofuranosyl)apramycin (24) along with the 6 alpha (25) and 6 beta (26) isomers. Similar reaction with the 6-hydroxy-5-O-THP derivative (20) or 11 gave only 25 and 26, but not 24. 17 was at least as active as apramycin against most Gram-positive and Gram-negative bacteria tested and more active than apramycin against most Gram-positive and Gram-negative bacteria tested and more active than apramycin against strains producing aminoglycoside-modifying enzymes. Strains of Pseudomonas aeruginosa were generally less sensitive to 17 than to apramycin. 24 was the most active of the three ribofuranosyl derivatives prepared though it was less active than 17.
6 - O -（3 - 氨基 - 3 - 脱氧 - α - D - 吡喃葡萄糖基）阿普拉霉素（17）是通过将阿普拉霉素的适当封闭的5,6 - 二羟基衍生物（11）与封闭的3 - 氨基葡萄糖基氯（15）进行糖苷化反应制备而成。阿普拉霉素的5 - 羟基 - 6 - O - 四氢吡喃基（THP）衍生物（19）的核糖基化反应生成了5 - O -（β - D - 呋喃核糖基）阿普拉霉素（24）以及6α（25）和6β（26）异构体。与6 - 羟基 - 5 - O - THP衍生物（20）或11进行类似反应时，只生成了25和26，而没有生成24。17对大多数测试的革兰氏阳性和革兰氏阴性细菌的活性至少与阿普拉霉素相当，并且对大多数测试的革兰氏阳性和革兰氏阴性细菌的活性比阿普拉霉素更高，对产生氨基糖苷修饰酶的菌株的活性也比阿普拉霉素更高。铜绿假单胞菌菌株对17的敏感性通常低于对阿普拉霉素的敏感性。24是所制备的三种呋喃核糖基衍生物中活性最高的，尽管其活性低于17。
