Work

Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums

Year: 2013

Type: article

Abstract: Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization-nucleophilic addition to yield tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.

Source: ACS Combinatorial Science

DOI: 10.1021/co3001567

Authors: Agustina La Venia, Bohumil Dolenský, Viktor Krchňák

Institutions: University of Notre Dame, Palacký University Olomouc, University of Chemistry and Technology, Prague

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: University of Notre Dame, Grantová Agentura České Republiky, European Social Fund

Awards: Solid-phase synthesis of diversely constrained peptidomimetics., G6359186121, G6461011143