DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY
DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY
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DOI：
10.7164/antibiotics.43.830
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发表时间：
1990-07-01
影响因子：
3.3
通讯作者：
ZEECK, A
中科院分区：
文献类型：
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作者：
HENKEL, T;ZEECK, A
为了继续我们对安古霉素类抗生素的结构-活性研究，我们通过在l -密糖部分上加入不同醇的区域选择性和非对映选择性的亲核方式制备了萨卡霉素A(1)和B(4)的衍生物。硅基化对1中的4”羟基的可逆保护使得两个l -针叶糖部分衍生化而不环化成桂醛b。在l -针叶糖部分发生变化后，体外细胞毒活性几乎保持不变，而糖元结构的变化导致生物活性完全丧失。
In continuation of our structure-activity investigations on angucycline antibiotics we prepared derivatives of saquayamycins A (1) and B (4) by regio- and diastereoselective nucleophilic addition of different alcohols to the L-aculose moiety. Reversible protection of the 4''-hydroxy group in 1 by silylation allowed a derivatization at both L-aculose moieties without cyclization towards cinerulose B. The in vitro cytotoxic activity remained almost unchanged after variation at the L-aculose moieties whereas a change in the aglycone structure led to a total loss of the biological activity.