An effective organic solvent system for the dissolution of amino acids.
Dimethylformamide containing strong acids (CF3 COOH, HBF4, TosOH, etc.) and an excess of tertiary base with pK < or = 6 is an effective solvent system for the dissolution of amino acids and their derivatives. The preferable base is pyridine, which forms a system with an apparent pH of 5.3. Amino acids dissolved in this solvent system readily interact with acylating reagents (BOC(2)O, ZOSu, Fmoc-OSu and activated derivatives of N-protected amino acids). A number of BOC-, Z-, Fmoc-amino acids, as well as several dipeptides, were synthesized using this solvent system with 80-99% yields.
Mitin
Y V
YV
Laboratory of Peptide Chemistry, Institute of Protein Research, Russian Academy of Sciences, Moscow Region.
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007526:Isoelectric Point; D011725:Pyridines / Q000737:chemistry; D012995:Solubility; D012997:Solvents / Q000737:chemistry*; D013997:Time Factors
D000596:Amino Acids; D011725:Pyridines; D012997:Solvents; D004126:Dimethylformamide; C023666:pyridine