Evidence map›Paper›PMID 41985886›Full record

ArticleJournal of the American Chemical Society2026

Bridging Heterocycle-Mediated Hydrogen Bonding Facilitates Permeability of Polar Macrobicycles.

Gabriella I D Cooper, Botao Dai, Noah Durham, Gilbert L Walker, Hongyi Yu, Angel Mendoza, Salvador J Bernardino, Yun-Dong Wu, Patrick G Harran

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

9 authors.

Gabriella I D CooperDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Botao DaiSchool of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Noah DurhamDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Gilbert L WalkerDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Hongyi YuDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Angel MendozaDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.ORCID 0009-0000-2435-5584
Salvador J BernardinoDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Yun-Dong WuSchool of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.ORCID 0000-0003-4477-7332
Patrick G HarranDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.ORCID 0000-0001-8748-5167

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Octafluorocyclopentene engages linear, unprotected peptides in relative-rate-controlled polysubstitution cascades. In one flask at ambient temperature, the reactions generate stable, fluoro-crowned macrobicyclic structures that display dual-loop surfaces. A subset of these molecules was found to have unusually high membrane permeability, as measured by PAMPA. Structures with a bridging imidazole unit were overrepresented in this group. To probe this finding, a larger set of compounds was synthesized wherein peripheral functionality and the bridging residue were incrementally varied. Crystallographic data, NMR studies, and MD simulations indicate the imidazole-bridged structures adopt conformations stabilized by internal H-bonding. The heterocycle further serves to occlude cavity water and allows macrobicycles harboring polar residues, such as serine and aspartate, to retain passive permeability. Calculations reveal a quantity termed 'desolvation cost efficiency' that is predictive of PAMPA performance. This parameter may be leveraged for the

Indexed as

Heterocyclic CompoundsMacrocyclic CompoundsHydrogen BondingModels, MolecularMolecular Dynamics SimulationPermeabilityHeterocyclic CompoundsMacrocyclic Compounds

Identifiers

PMID41985886
PMCPMC13134636

What OpenQuestion holds

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LicenceCC BY
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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.