ArticleNature protocols2010
Synthesis of peptide macrocycles using unprotected amino aldehydes.
Article in Nature protocols, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- 3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.Chemical science · 2020Article
- Cascade reactions of nitrogen-substituted isocyanates: a new tool in heterocyclic chemistry.Chemical science · 2016Article
- A genetically encoded aldehyde for rapid protein labelling.Chemical communications (Cambridge, England) · 2014Article
- Template-constrained macrocyclic peptides prepared from native, unprotected precursors.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
- Convergent synthesis of aminomethylene peptidomimetics.Nature protocols · 2012Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
This protocol describes a method for synthesizing peptide macrocycles from linear peptide precursors, isocyanides and aziridine aldehydes. The effects of the reaction components on the efficiency of the process are discussed. Macrocyclization is exemplified by the preparation of a nine-membered ring peptide macrocycle. The product is further functionalized by nucleophilic opening of the aziridine ring with a fluorescent thiol. This transformation constitutes a useful late-stage functionalization of a macrocyclic peptide molecule. The experimental section describes the selection of the required starting materials, and the preparation of a representative aziridine-2-carboxaldehyde dimer. The synthesis and isolation of the peptide macrocycle can be accomplished in 6 h, and the ring-opening requires approximately 6-8 h. The aziridine-2-carboxaldehyde reagent is commercially available or can be synthesized from readily available starting materials in approximately 4 d. The strategy described is not limited to the specific peptide, isocyanide, aziridine aldehyde or nucleophile used in the representative synthesis.
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Registered trials
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