[Free amino acids in the synthesis of peptides. Effect of inorganic compounds on the solubility of amino acids in aprotic solvents].
In order to increase the solubility of free amino acids so that they could be used in peptide synthesis, a system consisting of dimethylformamide, an inorganic additive, and pyridine was suggested. Compounds BF3, AlCl3, SnCl2, SiCl4, ZnCl2, SbCl3, CaCl2, BaI2, CdI2, and NaI can serve as the additives. Acylation of amino acids in such a solution (pH 5.2-5.3) with pentafluorophenyl esters of N alpha-protected amino acids gave N alpha-protected di- and tripeptides in a yield of more than 90%.
Riadnov
M G
MG
Institute of Protein Research, Russian Academy of Sciences, Pushchino, Moscow oblast, Russia.
Kashparova
N Ia
NIa
Kashparov
I A
IA
Mitin
Iu V
IuV
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007454:Iodides / Q000737:chemistry*; D007700:Kinetics; D009842:Oligopeptides / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry; D012995:Solubility; D012997:Solvents / Q000737:chemistry
D000596:Amino Acids; D002712:Chlorides; D007454:Iodides; D009842:Oligopeptides; D011725:Pyridines; D012997:Solvents; D004126:Dimethylformamide; C023666:pyridine; D005459:Fluorides