C. Bazewicz, Jacob S. Lipkin, Kristen A. Lozinak
Dec 21, 2011
Citations
0
Influential Citations
5
Citations
Journal
Tetrahedron Letters
Abstract
Abstract N-(tert-butoxycarbonyl)-4-cyano- l -phenylalanine methyl ester and three isotopomers (C15N, 13CN, and 13C15N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.