DOI: 10.5061/dryad.djh9w0wd0
title: Data for: On-resin synthesis and late-stage functionalization of macrocyclic atosiban mimetics via 5-iodo-1,4-triazoles

description: 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.
description: # Data for: On-resin synthesis and late-stage functionalization of
 macrocyclic atosiban mimetics via 5-iodo-1,4-triazoles 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.