DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY

被引:17
作者
HENKEL, T [1 ]
ZEECK, A [1 ]
机构
[1] UNIV GOTTINGEN,INST ORGAN CHEM,TAMMANNSTR 2,W-3400 GOTTINGEN,GERMANY
关键词
D O I
10.7164/antibiotics.43.830
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
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. © 1990, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.
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页码:830 / 837
页数:8
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