天然多环内酰胺和多环衍生物产生的跨环周环反应:优化生物成因挑战化学合成

IF 10.6 1区 化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY
Rosana Alvarez , Angel R. de Lera
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引用次数: 6

摘要

涵盖时间为1992年至2020-11-20年底。遗传编码的多基因大内酰胺是由Nature利用杂化聚酮合成酶/非核糖体肽合成酶(pks /NRPSs)装配线构建的,是从细菌中分离出来的大量天然产物的一部分。这些微生物中隐秘(即沉默)基因簇的激活最近允许产生并最终分离出该家族的其他成员。由于两个不饱和的片段被短的饱和链分开,一级环内酰胺被认为可以进行跨环反应和进一步的重排,从而产生结构多样的多环(天然)产物和氧化衍生物。这篇综述将涵盖科学家所面临的挑战,从生产微生物的培养物中分离这些不稳定化合物,它们的结构特征,生物活性,优化的生物遗传途径,以及由多聚片段的周环反应衍生的天然大内酰胺的初级结构的骨架重排。本文还将报道合成化学家模仿大自然成功生成这些天然产物并对其结构进行确认的努力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Natural polyenic macrolactams and polycyclic derivatives generated by transannular pericyclic reactions: optimized biogenesis challenging chemical synthesis

Natural polyenic macrolactams and polycyclic derivatives generated by transannular pericyclic reactions: optimized biogenesis challenging chemical synthesis

Covering from 1992 to the end of 2020-11-20.

Genetically-encoded polyenic macrolactams, which are constructed by Nature using hybrid polyketide synthase/nonribosomal peptide synthase (PKSs/NRPSs) assembly lines, are part of the large collection of natural products isolated from bacteria. Activation of cryptic (i.e., silent) gene clusters in these microorganisms has more recently allowed to generate and eventually isolate additional members of the family. Having two unsaturated fragments separated by short saturated chains, the primary macrolactam is posited to undergo transannular reactions and further rearrangements thus leading to the generation of a structurally diverse collection of polycyclic (natural) products and oxidized derivatives. The review will cover the challenges that scientists face on the isolation of these unstable compounds from the cultures of the producing microorganisms, their structural characterization, biological activities, optimized biogenetic routes, as well as the skeletal rearrangements of the primary structures of the natural macrolactams derived from pericyclic reactions of the polyenic fragments. The efforts of the synthetic chemists to emulate Nature on the successful generation and structural confirmation of these natural products will also be reported.

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来源期刊
Natural Product Reports
Natural Product Reports 化学-生化与分子生物学
CiteScore
21.20
自引率
3.40%
发文量
127
审稿时长
1.7 months
期刊介绍: Natural Product Reports (NPR) serves as a pivotal critical review journal propelling advancements in all facets of natural products research, encompassing isolation, structural and stereochemical determination, biosynthesis, biological activity, and synthesis. With a broad scope, NPR extends its influence into the wider bioinorganic, bioorganic, and chemical biology communities. Covering areas such as enzymology, nucleic acids, genetics, chemical ecology, carbohydrates, primary and secondary metabolism, and analytical techniques, the journal provides insightful articles focusing on key developments shaping the field, rather than offering exhaustive overviews of all results. NPR encourages authors to infuse their perspectives on developments, trends, and future directions, fostering a dynamic exchange of ideas within the natural products research community.
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