ArticleAmino acids2022
Structural diversity using amino acid "Customizable Units": conversion of hydroxyproline (Hyp) into nitrogen heterocycles.
Article in Amino acids, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 3 citations in OpenAlex.
- Decarboxylative-Allylation of Pyroglutamic Acid Derivatives: Stereocontrolled Access to Acyclic and Conformationally Restricted α,γ-Disubstituted γ-Amino Acids.Molecules (Basel, Switzerland) · 2026Article
- Antifungal Peptides with Unexpected Structure from a Library of Synthetic Analogs of Host-Defense Peptide Rigin.International journal of molecular sciences · 2025Article
- Short Synthesis of Structurally DiverseInternational journal of molecular sciences · 2025Article
- Conversion of Hydroxyproline "Doubly Customizable Units" to Hexahydropyrimidines: Access to Conformationally Constrained Peptides.The Journal of organic chemistry · 2023Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The ability of amino acid "customizable units" to generate structural diversity is illustrated by the conversion of 4-hydroxyproline (Hyp) units into a variety of nitrogen heterocycles. After a first common step, where the unit underwent a one-pot decarboxylation-alkylation reaction to afford 2-alkylpyrrolidines with high stereoselectivity, a divergent step was carried out. Thus, the deprotected 4-hydroxy group was used either to initiate a radical scission that afforded aliphatic β-amino aldehydes, or to carry out an elimination reaction, to give 2-alkyl-2,5-dihydro-1H-pyrroles. In the first case, the amines underwent a tandem reductive amination-cyclization to afford β-amino-δ-lactams, an efficient rigidifying unit in peptides. Different lactam N-substituents, such as alkylamines, peptides, and alkenyl chains suitable for olefin metathesis were introduced this way. In the second case, the pyrrole derivatives were efficiently converted into alkaloid and iminosugar derivatives in good global yields and with excellent stereoselectivity.
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Registered trials
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