Work

Asymmetric synthesis of vinylogous β-amino acids and their incorporation into mixed backbone oligomers

Year: 2017

Type: article

Abstract: Chiral vinylogous β-amino acids (VBAA) were synthesized using enantioselective Mannich reactions of aldehydes with in situ generated N-carbamoyl imines followed by a Horner-Wadsworth-Emmons reaction. The efficiency with which these units could be incorporated into oligomers with different moieties on the C- and N-terminal sides was established, as was the feasibility of sequencing oligomers containing VBAAs by tandem mass spectrometry. The data show that VBAAs will be useful building blocks for the construction of combinatorial libraries of peptidomimetic compounds.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c7ob00333a

Authors: Hao Wu, Hongchan An, Shuting (Cynthia) Mo, Thomas Kodadek

Institutions: Scripps Research Institute, Jupiter (United States)

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Institute on Aging

Awards: G1514839179, G3933092573