AMINOGLYCOSIDE ANTIBIOTICS - STUDIES DIRECTED TOWARD SELECTIVE MODIFICATION OF HYDROXYL-GROUPS - SYNTHESIS OF 3'-EPIPAROMAMINE AND 3'-EPINEAMINE
AMINOGLYCOSIDE ANTIBIOTICS - STUDIES DIRECTED TOWARD SELECTIVE MODIFICATION OF HYDROXYL-GROUPS - SYNTHESIS OF 3'-EPIPAROMAMINE AND 3'-EPINEAMINE
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DOI：
10.1139/v78-245
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发表时间：
1978-01-01
影响因子：
1.1
通讯作者：
NAKAGAWA, T
中科院分区：
文献类型：
--
作者：
HANESSIAN, S;MASSE, R;NAKAGAWA, T
基于某些细菌菌株可以产生能够磷酸化一系列氨基糖苷类抗生素的3''-羟基的酶的知识，以巴罗明为原料，通过一系列高产率步骤制备了假二糖3''-表帕罗明。选择性卤化和随后的胺化反应的应用使得3''-表帕罗明有效转化为3''-表帕罗胺。这两种化合物不是失活酶的底物，但与母体化合物巴洛马明和新胺相比，它们也是弱得多的抗生素。还报道了 2-氨基-2-脱氧-D-葡萄糖系列的模型合成研究。
Based on the knowledge that certain bacterial strains can produce enzymes that are capable of phosphorylating the 3''-hydroxyl group of a series of aminoglycoside antibiotics, the pseudodisaccharide 3''-epiparomamine was prepared through a series of high yielding steps, starting from paromamine. Application of selective halogenation and subsequent amination reactions allowed the efficient transformation of 3''-epiparomamine to 3''-epineamine. The 2 compounds were not substrates for the inactivating enzymes, but they were also much weaker antibiotics compared to the parent compounds paromamine and neamine. Model synthetic studies in the 2-amino-2-deoxy-D-glucose series are also reported.