Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
Abstract
The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction.
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CuAAC has generated the highest interest for producing QA antimicrobial surfaces.
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- Authors
- Tornøe, C. W., Christensen, C., & Meldal, M.
- Affiliations
- Carlsberg Laboratory (DK)
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-04-02
- Volume
- 67
- Issue
- 9
- Pages
- 3057-3064
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1968652549
- Cited by
- 8,696
- References
- 11
- Citations by year
- 2026: 236 · 2025: 299 · 2024: 360 · 2023: 394 · 2022: 311 · 2021: 360 · 2020: 414 · 2019: 399 · 2018: 402 · 2017: 440 · 2016: 520 · 2015: 498 · 2014: 596 · 2013: 553 · 2012: 552
- FWCI
- 38.78
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Physical Sciences › Chemistry › Organic Chemistry › Catalytic Alkyne Reactions
- Keywords
- 1,2,3-triazoles, azide, terminal alkynes, solid-phase peptide synthesis, regiospecificity, azido sugars, X-ray crystal structure, Mitsunobu reaction, peptide side chains
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