Naturally Occurring Dimers from Chemical Perspective

Lian, Gaoyan; Yu, Bo

doi:10.1002/cbdv.201000038

Cited by 66 publications

(47 citation statements)

References 200 publications

(87 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the 2004 Greers analysis of natural products, which includes over 3000 literature entries, [1] up to 7 % of them are homodimeric full bilaterally symmetric compounds exhibiting remarkable pharmacological profiles, although the biological role of symmetry in these structures is not yet fully understood. [2] NMR-spectroscopy-based structure elucidation of homodimers is challenging, since the two monomeric parts provide the same set of NMR signals and therefore NOEs between equivalent protons cannot be observed, unless the symmetry is broken in 13 C, 1 H-HSQC-NOESY experiments. [3] In addition, intra-and intermonomer NOE correlations are difficult to discern.…”

mentioning

confidence: 99%

Residual Dipolar Coupling Enhanced NMR Spectroscopy and Chiroptics: A Powerful Combination for the Complete Elucidation of Symmetrical Small Molecules

Pérez‐Balado

Sun

Griesinger

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

mentioning

confidence: 99%

Residual Dipolar Coupling Enhanced NMR Spectroscopy and Chiroptics: A Powerful Combination for the Complete Elucidation of Symmetrical Small Molecules

Pérez‐Balado

Sun

Griesinger

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

“…Although it is not uncommon to find dimers of natural products, [9] what is unusual about the structure of 5 is that the bridging methylene carbon, C-10, could not be accounted for in the monomeric unit, implying that a 1-carbon building block is involved in the dimer formation. The number of 1-carbon building blocks in nature is fairly limited, with S -adenosyl methionine and formaldehyde being the two most common.…”

mentioning

confidence: 99%

Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Legako

et al. 2016

Chemistry A European J

View full text Add to dashboard Cite

Dibohemamines A–C (5–7), three novel dimeric bohemamine analogs dimerized through a methylene group, were isolated from a marine-derived Streptomyces spinoverrucosus. The structures determined by spectroscopic analysis were confirmed through the semi-synthetic derivatization of monomeric bohemamines and formaldehyde. These reactions, which could occur under mild conditions, together with the detection of formaldehyde in the culture, revealed that this dimerization is a non-enzymatic process. In addition to the unique dimerization of the dibohemamines, dibohemamines B and C were found to have nM cytotoxicity against the non-small cell lung cancer cell line A549. In view of the potent cytotoxicity of compounds 6 and 7, a small library of bohemamine analogs w as generated for biological evaluation by utilizing a series of aryl and alkyl aldehydes.

show abstract

“…This compound contains two hexahydropyrroloindole substructures that are connected at vicinal quaternary stereocenters to form a dimeric molecule 48) (Chart 5A). Currently, more than 600 dimeric natural products have been reported to date, among which nearly 100 are dimeric diketopiperazines.…”

Section: Functional Analysis Of a Cytochrome P450 As Dimerization Catmentioning

confidence: 99%

“…Currently, more than 600 dimeric natural products have been reported to date, among which nearly 100 are dimeric diketopiperazines. [47][48][49][50][51][52][53][54][55][56][57][58][59][60] Dimeric natural products exhibit various biological activities, [49][50][51] and dimerization is thought to contribute toward conferring bioactivity to these products. 61) In this section, we will outline our study on the enzymes involved in the biosynthesis of 10 that is aimed at understanding the biosynthetic mechanism of the formation of dimeric natural products.…”

Section: Functional Analysis Of a Cytochrome P450 As Dimerization Catmentioning

confidence: 99%

Effective Use of Heterologous Hosts for Characterization of Biosynthetic Enzymes Allows Production of Natural Products and Promotes New Natural Product Discovery

Watanabe

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

In the past few years, there has been impressive progress in elucidating the mechanism of biosynthesis of various natural products accomplished through the use of genetic, molecular biological and biochemical techniques. Here, we present a comprehensive overview of the current results from our studies on fungal natural product biosynthetic enzymes, including nonribosomal peptide synthetase and polyketide synthasenonribosomal peptide synthetase hybrid synthetase, as well as auxiliary enzymes, such as methyltransferases and oxygenases. Specifically, biosynthesis of the following compounds is described in detail: (i) Sch210972, potentially involving a Diels-Alder reaction that may be catalyzed by CghA, a functionally unknown protein identified by targeted gene disruption in the wild type fungus; (ii) chaetoglobosin A, formed via multi-step oxidations catalyzed by three redox enzymes, one flavin-containing monooxygenase and two cytochrome P450 oxygenases as characterized by in vivo biotransformation of relevant intermediates in our engineered Saccharomyces cerevisiae; (iii) ( )-ditryptophenaline, formed by a cytochrome P450, revealing the dimerization mechanism for the biosynthesis of diketopiperazine alkaloids; (iv) pseurotins, whose variations in the Cand O-methylations and the degree of oxidation are introduced combinatorially by multiple redox enzymes; and (v) spirotryprostatins, whose spiro-carbon moiety is formed by a flavin-containing monooxygenase or a cytochrome P450 as determined by heterologous de novo production of the biosynthetic intermediates and final products in Aspergillus niger. We close our discussion by summarizing some of the key techniques that have facilitated the discovery of new natural products, production of their analogs and identification of biosynthetic mechanisms in our study.

show abstract

Naturally Occurring Dimers from Chemical Perspective

Cited by 66 publications

References 200 publications

Residual Dipolar Coupling Enhanced NMR Spectroscopy and Chiroptics: A Powerful Combination for the Complete Elucidation of Symmetrical Small Molecules

Residual Dipolar Coupling Enhanced NMR Spectroscopy and Chiroptics: A Powerful Combination for the Complete Elucidation of Symmetrical Small Molecules

Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Effective Use of Heterologous Hosts for Characterization of Biosynthetic Enzymes Allows Production of Natural Products and Promotes New Natural Product Discovery

Contact Info

Product

Resources

About