Application of High-Throughput Competition Experiments in the Development of Aspartate-Directed Site-Selective Modification of Tyrosine Residues in Peptides.

Alex J Chinn, Jaeyeon Hwang, Byoungmoo Kim, Craig A Parish, Shane W Krska, Scott J Miller

Abstract read

In one paragraph

Article in The Journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing papers in PubMed

–field-weighted citation impact

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

1 citing paper in PubMed.

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation.Chemical science · 2023
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

6 authors.

Alex J ChinnDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.

Jaeyeon HwangDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.

Byoungmoo KimDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.ORCID 0000-0002-1428-7896

Craig A ParishDiscovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.ORCID 0000-0002-7162-3542

Shane W KrskaDiscovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.ORCID 0000-0001-9757-9036

Scott J MillerDepartment of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.ORCID 0000-0001-7817-1318

Funding

Site-Selective Catalysis for Bioactive Scaffold DiversificationR35GM132092 · NIGMS · YALE UNIVERSITY · PI Scott J Miller · 2019 to 2026

$6.3M

NIGMS NIH HHS R35 GM132092

6 · The paper itself

Abstract

Herein we report a Cu-catalyzed, site-selective functionalization of peptides that employs an aspartic acid (Asp) as a native directing motif, which directs the site of O-arylation at a proximal tyrosine (Tyr) residue. Through a series of competition studies conducted in high-throughput reaction arrays, effective conditions were identified that gave high selectivity for the proximal Tyr in Asp-directed Tyr modification. Good levels of site-selectivity were achieved in the O-arylation at a proximal Tyr residue in a number of cases, including a peptide-small molecule hybrid.

Indexed as

Aspartic AcidTyrosineAmino Acid SequencePeptidesAspartic AcidPeptidesTyrosine

Identifiers

PMID32614587

DOI10.1021/acs.joc.0c01147

PMCPMC7966973

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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.