Investigating Bicyclobutane–Triazolinedione Cycloadditions as a Tool for Peptide Modification

Acyl bicyclobutanes are shown to engage in strain-promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptide-derived triazolinediones that undergo cyclo...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2022-02, Vol.24 (6), p.1268-1273
Main Authors: Schwartz, Brett D, Smyth, Aidan P, Nashar, Philippe E, Gardiner, Michael G, Malins, Lara R
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Bridged Bicyclo Compounds - chemistry
Cycloaddition Reaction
Molecular Structure
Peptides - chemistry
Triazoles - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Acyl bicyclobutanes are shown to engage in strain-promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptide-derived triazolinediones that undergo cycloaddition reactions to afford novel peptide conjugates. The additive-free and fully atom-economical nature of the transformation is a promising starting point for the generalization of this cycloaddition reaction for the functionalization of biomolecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04071