Data for: On-resin synthesis and late-stage functionalization of macrocyclic atosiban mimetics via 5-iodo-1,4-triazoles
Data files
Sep 18, 2025 version files 4.28 MB
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README.md
2.56 KB
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SI_Final_DRYAD.pdf
4.27 MB
Abstract
We report an on-resin strategy for synthesizing 5-iodo-1,4-disubstituted-1,2,3-triazole-containing macrocyclic peptides as multifunctional disulfide bond mimetics. Optimized CuAAC and Suzuki-Miyaura conditions enabled late-stage arylation at the triazole 5-position. This approach allowed fluorescent and biotin peptide labelling without traditional N-terminal linkers. Structural analysis revealed that the 5-iodo substituent influences peptide conformation. These findings establish 5-iodo-1,4-triazoles as versatile, tunable motifs for macrocyclization and functionalization, expanding the chemical space accessible for macrocyclic peptide chemical biology tools and therapeutics.
Dataset DOI: [10.5061/dryad.djh9w0wd0]
We have submitted our raw data (SI_Final_DRYAD.pdf)
Description of SI_Final_DRYAD.pdf
This PDF contains all the supporting information. This begins with general reagents, instrumentation, and detailed general synthetic protocols. Following this, general supporting figures that provide further detail to the discussion of the manuscript are included. The general supporting figures include stacked RP-HPLC traces (images) with zooms (images) of the discussed regions. The experimental section has a table of the final peptide compounds along with their synthetic methods and characterisation in the form of RP-HPLC, LC-MS, 1H NMR, and IR, where applicable (for details regarding each form of characterisation, see below). The final section of the experiment includes an appendix where tables are included for the standardization of the reaction. For each table entry, a crude RP-HPLC trace is provided. LCMS is provided following the crude RP-HPLC traces to identify the main components of the standardised reactions.
- RP-HPLC characterisation data (images) are provided with compound number, tR (retention time), and gradient on the spectrum. Peptide purity is provided in the figure caption.
- LCMS characterisation data (images) is provided with compound number and m/z charge states identified with deconvolution presented in the figure caption.
- 1H NMR (images) is provided to specifically view the presence/absence of the specific aromatic proton at the 5 position of the triazole ring, as well as proline isomers. It is provided for those compounds where this is relevant (2-4).
- IR (images) is provided for compounds (3 and 4) to identify the absence of an alkyne peak and is provided alongside a spectrum of the peptide with an alkyne peak (1*) for reference.
Sharing/Access information
NMR, LC-MS, RP-HPLC, and IR data will be available as images in the supporting information.
Code/Software
MestReNova was used to view and assign the NMR data following collection with Bruker 400 MHZ NMR equipment.
The spectra found in the PDF file can be directly viewed without any NMR software.
Chemical and peptide structures were created using ChemDraw and can be directly viewed without any ChemDraw software.
Access information
Other publicly accessible locations of the data:
- Not applicable.
Data was derived from the following sources:
- Not applicable.