Evidence map›Paper›PMID 28580785›Full record

ReviewChemical reviews2017

Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Christopher R Shugrue, Scott J Miller

Open access · greenAbstract readReview
In one paragraph

Review in Chemical reviews, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 57 papers.

0numbers the graph read from it
0cells of the map it votes in
57citing papers in PubMed
17.2field-weighted citation impact, top 1% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

57 citing papers in PubMed, 203 citations in OpenAlex.

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  13. Kinetics and Mechanism of Azole n-π*-Catalyzed Amine Acylation.Journal of the American Chemical Society · 2023
    Article
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  20. Chiral Amines via Enantioselective π-Allyliridium-Accounts of chemical research · 2022
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors at 1 institution in 1 country.

Christopher R ShugrueDepartment of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520, United States.ORCID http://orcid.org/0000-0002-3504-9475
Scott J MillerDepartment of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520, United States.ORCID http://orcid.org/0000-0001-7817-1318
Yale University · US

Funding

Site-Selective Catalysis for Organic SynthesisR37GM068649 · NIGMS · YALE UNIVERSITY · PI MILLER, SCOTT J · 2011 to 2018
$2.7M
Selective Peptide-Based Oxidation Catalysts for Bioactive Molecule SynthesisR01GM096403 · NIGMS · YALE UNIVERSITY · PI MILLER, SCOTT J · 2011 to 2018
$2.4M
Site-Selective Catalysts for Organic SynthesisR01GM068649 · NIGMS · YALE UNIVERSITY · PI MILLER, SCOTT J · 2003 to 2010
$2.3M
NIGMS NIH HHS R01 GM068649NIGMS NIH HHS R01 GM096403NIGMS NIH HHS R37 GM068649
6 · The paper itself

Abstract

The application of small molecules as catalysts for the diversification of natural product scaffolds is reviewed. Specifically, principles that relate to the selectivity challenges intrinsic to complex molecular scaffolds are summarized. The synthesis of analogues of natural products by this approach is then described as a quintessential "late-stage functionalization" exercise wherein natural products serve as the lead scaffolds. Given the historical application of enzymatic catalysts to the site-selective alteration of complex molecules, the focus of this Review is on the recent studies of nonenzymatic catalysts. Reactions involving hydroxyl group derivatization with a variety of electrophilic reagents are discussed. C-H bond functionalizations that lead to oxidations, aminations, and halogenations are also presented. Several examples of site-selective olefin functionalizations and C-C bond formations are also included. Numerous classes of natural products have been subjected to these studies of site-selective alteration including polyketides, glycopeptides, terpenoids, macrolides, alkaloids, carbohydrates, and others. What emerges is a platform for chemical remodeling of naturally occurring scaffolds that targets virtually all known chemical functionalities and microenvironments. However, challenges for the design of very broad classes of catalysts, with even broader selectivity demands (e.g., stereoselectivity, functional group selectivity, and site-selectivity) persist. Yet, a significant spectrum of powerful, catalytic alterations of complex natural products now exists such that expansion of scope seems inevitable. Several instances of biological activity assays of remodeled natural product derivatives are also presented. These reports may foreshadow further interdisciplinary impacts for catalytic remodeling of natural products, including contributions to SAR development, mode of action studies, and eventually medicinal chemistry.

Indexed as

Biological ProductsCatalysisMolecular ConformationSmall Molecule LibrariesBiological ProductsSmall Molecule Libraries

Identifiers

PMID28580785
PMCPMC5742423
OpenAlexW2624370041

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.