Biosynthesis of pyrroloindoline-containing natural products

Sun, Chenghai; Tian, Wenya; Lin, Zhi; Qu, Xudong

doi:10.1039/d2np00030j

Cited by 40 publications

(30 citation statements)

References 262 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… 21 ; Sun et al. 22 ). From our point of view, the controllable diverse dimerization could even be regarded as “yardsticks” to measure progress in the art and science of controlling chemoselectivity, which nature has practiced deftly for billions of years but man has yet to master (Shenvi et al.…”

Section: Before You Beginmentioning

confidence: 99%

A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs

Bai

Jiang

2023

STAR Protocols

View full text Add to dashboard Cite

Section: Before You Beginmentioning

confidence: 99%

A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs

Bai

Jiang

2023

STAR Protocols

View full text Add to dashboard Cite

“…Because of their high structural diversity and occurrence in many natural products and bioactive molecules, many methods have been developed to synthesize these compounds, including Friedel-Crafts alkylation, transition metal catalyzed cyclization, free radical cyclization, and cascade reactions, among others. [40,[114][115][116][117] However, there are relatively few cases of their synthesis in water.…”

Section: Annulation Reactionsmentioning

confidence: 99%

Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Pang

Zuo

Zhang

et al. 2023

The Chemical Record

View full text Add to dashboard Cite

Indoles and their derivatives have dominated a significant proportion of nitrogen‐containing heterocyclic compounds and play an essential role in synthetic and medicinal chemistry, pesticides, and advanced materials. Compared with conventional synthetic strategies, direct functionalization of indoles provides straightforward access to construct diverse indole scaffolds. As we enter an era emphasizing green and sustainable chemistry, utilizing environment‐friendly solvents represented by water demonstrates great potential in synthesizing valuable indole derivatives. This review aims to depict the critical aspects of aqueous‐mediated indoles functionalization over the past decade and discusses the future challenges and prospects in this fast‐growing field. For the convenience of readers, this review is classified into three parts according to the bonding modes (C−C, C−N, and C−S bonds), which focus on the diversity of indole derivatives, the prominent role of water in the chemical process, and the types of catalyst systems and mechanisms. We hope this review can promote the sustainable development of the direct functionalization of indoles and their derivatives and the discovery of novel and practical organic methods in aqueous phase.

show abstract

“…Biogenetic studies of sulfur containing moieties in natural products [ 105 ], in particular those from marine organisms [ 106 ], as well as comprehensive report on the biosynthesis of pyrrolidinoindoline containing NPs, including BPI-ETPs [ 107 ], together with the flavoenzyme-catalyzed formation of disulfide bonds in natural products biosynthesis [ 108 , 109 ], have been previously covered. The biogenetic routes to these natural products are usually found in dedicated biosynthetic gene clusters [ 31 , 110 , 111 ].…”

Section: Biogenesis Of Bpi-etpsmentioning

confidence: 99%

Bispyrrolidinoindoline Epi(poly)thiodioxopiperazines (BPI-ETPs) and Simplified Mimetics: Structural Characterization, Bioactivities, and Total Synthesis

et al. 2022

View full text Add to dashboard Cite

Within the 2,5-dioxopiperazine-containing natural products generated by “head-to-tail” cyclization of peptides, those derived from tryptophan allow further structural diversification due to the rich chemical reactivity of the indole heterocycle, which can generate tetracyclic fragments of hexahydropyrrolo[2,3-b]indole or pyrrolidinoindoline skeleton fused to the 2,5-dioxopiperazine. Even more complex are the dimeric bispyrrolidinoindoline epi(poly)thiodioxopiperazines (BPI-ETPs), since they feature transannular (poly)sulfide bridges connecting C3 and C6 of their 2,5-dioxopiperazine rings. Homo- and heterodimers composed of diastereomeric epi(poly)thiodioxopiperazines increase the complexity of the family. Furthermore, putative biogenetically generated downstream metabolites with C11 and C11’-hydroxylated cores, as well as deoxygenated and/or oxidized side chain counterparts, have also been described. The isolation of these complex polycyclic tryptophan-derived alkaloids from the classical sources, their structural characterization, the description of the relevant biological activities and putative biogenetic routes, and the synthetic efforts to generate and confirm their structures and also to prepare and further evaluate structurally simple analogs will be reported.

show abstract

Biosynthesis of pyrroloindoline-containing natural products

Abstract: Recent research on the biosynthesis of pyrroloindoline-containing natural products, including studies investigating their biosynthetic mechanisms and engineering biosynthetic pathways to produce novel products.

Cited by 40 publications

References 262 publications

A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs

A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs

Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Bispyrrolidinoindoline Epi(poly)thiodioxopiperazines (BPI-ETPs) and Simplified Mimetics: Structural Characterization, Bioactivities, and Total Synthesis

Contact Info

Product

Resources

About