Evidence map›Paper›PMID 38810019›Full record

ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024

Peptide Boronic Acids by Late-Stage Hydroboration on the Solid Phase.

Marius Werner, Julian Brinkhofer, Leon Hammermüller, Thomas Heim, Truc Lam Pham, Jonas Huber, Christian Klein, Franziska Thomas

Abstract read
In one paragraph

Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Late-Stage Functionalization of Peptides on the Solid Phase.Angewandte Chemie (International ed. in English) · 2026
    Review
  3. Dynamic Anchoring of Peptides to the Extracellular Matrix Enabled by Boronic Acid.Chembiochem : a European journal of chemical biology · 2025
    Article
  4. Late-Stage Amination of Peptides on the Solid Phase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  5. Peptide Boronic Acids by Late-Stage Hydroboration on the Solid Phase.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    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

8 authors.

Marius WernerInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0000-0003-0926-2181
Julian BrinkhoferInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0009-0002-5722-6783
Leon HammermüllerInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0009-0009-9744-4460
Thomas HeimInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0009-0002-9541-892X
Truc Lam PhamInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0000-0003-3808-2083
Jonas HuberInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0009-0003-6392-4999
Christian KleinMedicinal Chemistry, Institute of Pharmacy and Molecular Biotechnology (IPMB), Heidelberg University, Im Neuenheimer Feld 364, 69120, Heidelberg, Germany.ORCID 0000-0003-3522-9182
Franziska ThomasInstitute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID 0000-0002-1176-7018

Funding

Bundesministerium für Bildung und Forschung (BMBF) ExU 6.1.16Deutsche Forschungsgemeinschaft 2082/1 390761711Deutsche Forschungsgemeinschaft 414261058Fonds der Chemischen IndustrieMax Planck SocietyMinistry of Science Baden-Württemberg also known as Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg
6 · The paper itself

Abstract

Organoboron compounds have a wide range of applications in numerous research fields, and methods to incorporate them in biomolecules are much sought after. Here, on-resin chemical syntheses of aliphatic and vinylogous peptide boronic acids are presented by transition metal-catalyzed late-stage hydroboration of alkene and alkyne groups in peptides and peptoids, for example on allyl- and propargylglycine residues, using readily available chemicals. These methods yield peptide boronic acids with much shorter linkers than previously reported on-resin methods. Furthermore, the methods are regio- and stereoselective, compatible with all canonical amino acid residues and can be applied to short, long, and in part even "difficult" peptide sequences. In a feasibility study, the protected peptide vinylboronic acids are further derivatized by the Petasis reaction using salicylaldehyde derivatives. The ability of the obtained peptide boronic acids to reversibly bind to carbohydrates is demonstrated in a catch-release model experiment using a fluorescently labeled peptide boronic acid on cross-linked dextran beads. In summary, this highlights the potential of the target compounds for drug discovery, glycan-specific target recognition, controlled release, and diagnostics.

Indexed as

Boronic AcidsPeptidesCatalysisSolid-Phase Synthesis TechniquesBoronic AcidsPeptideshydroborationlate‐stage functionalizationnonproteinogenic amino acidspeptidessolid‐phase synthesis

Identifiers

PMID38810019
PMCPMC11267286

What OpenQuestion holds

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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.