Evidence map›Paper›PMID 31018033›Full record

ArticleAngewandte Chemie (International ed. in English)2019

A Diene-Containing Noncanonical Amino Acid Enables Dual Functionality in Proteins: Rapid Diels-Alder Reaction with Maleimide or Proximity-Based Dimerization.

Andre H St Amant, Fengying Huang, Jia Lin, Keith Rickert, Vaheh Oganesyan, Daniel Lemen, Shenlan Mao, Jay Harper, Marcello Marelli, Herren Wu and 3 more

Open access · greenAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed
2.4field-weighted citation impact, top 12% 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

16 citing papers in PubMed, 31 citations in OpenAlex.

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  13. Hetero-Diels-Alder Cycloaddition with RAFT Polymers as Bioconjugation Platform.Angewandte Chemie (International ed. in English) · 2020
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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

13 authors at 3 institutions in 3 countries.

Andre H St AmantDepartment of Chemistry and Biochemistry, University of California - Santa Barbara, Santa Barbara, California, 93106, USA.ORCID 0000-0002-4842-1918
Fengying HuangAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Jia LinAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Keith RickertAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Vaheh OganesyanAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Daniel LemenAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Shenlan MaoAstraZeneca Oncology R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Jay HarperAstraZeneca Oncology R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Marcello MarelliAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Herren WuAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.
Changshou GaoAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.ORCID 0000-0002-5781-6559
Javier Read de AlanizDepartment of Chemistry and Biochemistry, University of California - Santa Barbara, Santa Barbara, California, 93106, USA.ORCID 0000-0003-2770-9477
R James ChristieAntibody Discovery and Protein Engineering Department, AstraZeneca Biopharmaceuticals R&D, One MedImmune Way, Gaithersburg, MD, 20878, USA.ORCID 0000-0002-8369-804X
AstraZeneca (United States) · USAstraZeneca (France) · FRUniversity of California, Santa Barbara · US

Funding

Upgrade of 500 MHz NMR SpectrometerS10OD012077 · OD · UNIVERSITY OF CALIFORNIA SANTA BARBARA · PI ZHANG, LIMING · 2013 to 2013
$347k
AstraZenecaNIH HHS S10 OD012077
6 · The paper itself

Abstract

Here, we describe a diene-containing noncanonical amino acid (ncAA) capable of undergoing fast and selective normal electron-demand Diels-Alder (DA) reactions following its incorporation into antibodies. A cyclopentadiene derivative of lysine (CpHK) served as the reactive handle for DA transformations and the substrate for genetic incorporation. CpHK incorporated into antibodies with high efficiency and was available for maleimide conjugation or self-reaction depending on position in the amino acid sequence. CpHK at position K274 reacted with the maleimide drug-linker AZ1508 at a rate of ≈79 m

Indexed as

AlkadienesAmino AcidsCycloaddition ReactionDimerizationHumansImmunoglobulin Fc FragmentsImmunoglobulin GMaleimidesModels, MolecularMolecular StructureAlkadienesAmino AcidsImmunoglobulin Fc FragmentsImmunoglobulin GmaleimideMaleimidesantibody-drug conjugateDiels-Alder reactiondienenon-canonical amino acidproximity-driven reaction

Identifiers

PMID31018033
PMCPMC6555655
OpenAlexW2942425574

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.