Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications

Org Lett. 2021 Aug 20;23(16):6288-6292. doi: 10.1021/acs.orglett.1c02084. Epub 2021 Aug 11.

Abstract

Isotopically labeled amino acids are widely used to study the structure and dynamics of proteins by NMR. Herein we describe a facile, gram-scale synthesis of compounds 1b and 2b under standard laboratory conditions from the common intermediate 7. 2b is obtained via simple deprotection, while 1b is accessed through a reductive deoxygenation/deuteration sequence and deprotection. 1b and 2b provide improved signal intensity using lower amounts of labeled precursor and are alternatives to existing labeling approaches.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenylalanine / chemistry*
  • Proteins
  • Tyrosine / chemical synthesis*
  • Tyrosine / chemistry

Substances

  • Amino Acids
  • Proteins
  • Tyrosine
  • Phenylalanine