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Privileged Structures as Peptide Backbone Constraints: Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone Peptides
journal contribution
posted on 2014-07-14, 00:00 authored by Pilar Ventosa-Andrés, Ludmila Hradilová, Viktor KrchňákA 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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Conventionalfunctionalizedcyclizationtarget compoundssyntheseacidintegritymicrowave conditionsPrivileged Structuresacylationsynthesispeptide backbonetandemPeptide Backbone ConstraintsSignificant epimerizationstereocontrolconstraintStereoselectiveefficiencystereogenic centerBenzimidazolinopiperazinone PeptidesASynthesiscaffold
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