Synthesis and 19F spectra of tetra‐L‐alanine analogs containing selectively incorporated 3‐fluoro‐l‐alanine residues

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Abstract
The synthesis of analogs of tetra-L-alanine containing 3-fluoro-L-alanine selectively incorporated at each position is described. The standard procedures in the literature used to couple L-alanine peptides together often led to undesired products, or elimination reactions when corresponding 3-fluoro-L-alanine peptide analogs were used. Several modified procedures were thus developed for the synthesis of fluorine-substituted analogs. In addition, the pH-dependence of 19F NMR spectra of 3-fluoro-L-alanine and the tetrapeptide analogs is presented.