Cyclobutyl-Containing Rigid Analogues of Threonine: Synthesis and Physical Chemical Properties

J Org Chem. 2017 Dec 1;82(23):12863-12868. doi: 10.1021/acs.joc.7b02259. Epub 2017 Nov 2.

Abstract

Hitherto unknown cis- and trans-1-amino-3-hydroxy-3-methylcyclobutanecarboxylic acids were synthesized in multigram scale. The obtained compounds can be considered as achiral conformationally restricted analogues of threonine with fixed spatial orientation of functional groups. pKa values are noticeably different for both amino acids. According to the X-ray data the cyclobutane rings in both compounds are almost planar (the corresponding torsion angles are below 7°).

Publication types

  • Research Support, Non-U.S. Gov't