SYNTHESIS OF PUTATIVE INTERMEDIATES ON THE MONENSIN BIOSYNTHETIC-PATHWAY AND INCORPORATION EXPERIMENTS WITH THE MONENSIN-PRODUCING ORGANISM

被引：28

作者：

HOLMES, DS ^{[1
]}

SHERRINGHAM, JA ^{[1
]}

DYER, UC ^{[1
]}

RUSSELL, ST ^{[1
]}

ROBINSON, JA ^{[1
]}

机构：

[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO9 5NH,HANTS,ENGLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 02期

关键词：

D O I：

10.1002/hlca.19900730203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As a direct test of the Cane‐Westley hypothesis concerning the mode of assembly of ether rings in the polyether class of ionophore antibiotics, we describe experiments culminating in the synthesis of three putative intermediates on the monensin biosynthetic pathway and incorporation experiments with these materials and the monensin‐producing organism Streptomyces cinnamonensis. The putative intermediates synthesised include the trienes [21‐3H]‐7 and [13‐3H]‐10, and the diene [9‐3H]‐11. The results of the incorporation experiments conducted with whole cell cultures suggest that [13‐3H]‐10 and [21‐3H]‐7 are unable to cross the intact cell membrane of S. cinnamonensis, whereas diene [9‐3H]‐11 can gain entry to the cellular interior, but is then degraded efficiently, most likely by a pathway closely related to β‐oxidation, without being specifically incorporated into the antibiotic. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：239 / 259

页数：21

共 57 条

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