Privileged structures as peptide backbone constraints: polymer-supported stereoselective synthesis of benzimidazolinopiperazinone peptides
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
24725105
DOI
10.1021/co500023k
Knihovny.cz E-resources
- MeSH
- Benzimidazoles chemical synthesis chemistry MeSH
- Microwaves MeSH
- Molecular Conformation MeSH
- Peptides chemical synthesis chemistry MeSH
- Piperazines chemical synthesis chemistry MeSH
- Polymers chemistry MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Benzimidazoles MeSH
- Peptides MeSH
- Piperazines MeSH
- Polymers MeSH
A molecular scaffold comprising a privileged structure was designed and synthesized to serve as a peptide backbone conformational constraint. The synthesis of highly functionalized 2,3,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-4(1H)-ones on a solid-phase support was performed via a tandem N-acyl-N-aryliminium ion cyclization-nucleophilic addition reaction. The synthesis proceeded with full stereocontrol of the newly formed stereogenic center. Conventional and microwave-assisted syntheses were compared with respect to efficiency and the optical integrity of the target compounds. Significant epimerization was observed during acylation with (S)- and (R)-2-bromopropionic acids under microwave conditions.
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