Work

Design, synthesis and characterization of structurally dynamic cyclic N , S -acetals

Year: 2020

Type: article

Abstract: We report the synthesis, characterization and comparison of a series of electronically perturbed, cyclic N,S-acetals. Inspired by electrophilic auxiliaries utilized for amine capture and concomitant peptide ligation, we studied these N,S-acetal systems and evaluated their propensity to generate zwitterionic intermediates in situ. Certain N,S-acetals in this study exhibit structurally dynamic properties through a solvent and pH-dependent ability to ring-open and ring-close via C1-S bond ionization at room temperature.

Source: Chemical Communications

DOI: 10.1039/d0cc03503c

Authors: Emily K. Kirkeby, Andrew G. Roberts

Institution: University of Utah

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 Utah, National Institutes of Health, National Institute of General Medical Sciences, National Center for Research Resources

Awards: EXTRAMURAL RESEARCH FACILITIES CONSTRUCTION, Pd-Catalyzed Olefin Functionalization Reactions for Organic Synthesis, A 500MHz NMR Spectrometer with Automation, G7623846777