Total synthesis and structure revision of petrobactin
Total synthesis and structure revision of petrobactin
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DOI：
10.1016/s0040-4020(03)00103-0
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发表时间：
2003-03-10
期刊：
影响因子：
2.1
通讯作者：
Butler, A
中科院分区：
文献类型：
--
作者：
Bergeron, RJ;Huang, GF;Butler, A
本文报道了从海洋细菌Marinophylcarbonoclasticus中分离得到的铁载体petrobactin的全合成和结构鉴定。合成中的关键步骤是N ′-（2，3-二苯甲酰氧基苯甲酰基）N4-苄基亚精胺与柠檬酸1，3-二（对硝基苯基）-2-叔丁酯缩合。合成产物的质子NMR谱与天然产物的质子NMR谱相比，显示该化合物不含2，3-二羟基苯甲酰基部分，相反，分裂模式表明3，4-二羟基苯甲酰基片段。通过类似途径获得3，4-二羟基苯甲酰基类似物;该化合物的质子和碳-13 NMR光谱与天然petrobactin的报告一致。(C)2003爱思唯尔科技有限公司版权所有。
The total synthesis and the revised structural assignment of petrobactin, a siderophore isolated from the marine bacterium Marinobacter hydrocarbonoclasticus, is reported. The key step in the synthesis involved condensation of N'-(2,3-dibenzoyloxybenzoyl)N 4-benzylspermidine with 1,3-di-(p-nitrophenyl)-2-tert-butyI citrate. Proton NMR spectra of the synthesized product compared with those reported for the natural product revealed that the compound did not contain 2,3-dihydroxybenzoyl moieties as published; instead, the splitting pattern suggested 3,4-dihydroxybenzoyl fragments. The 3,4-dihydroxybenzoyl analogue was accessed via a similar route; the proton and carbon-13 NMR spectra of this compound were consistent with those reported for natural petrobactin. (C) 2003 Elsevier Science Ltd. All rights reserved.