A method for preparation of amino acid thiohydantoins from free amino acids activated by acetyl chloride for development of protein C-terminal sequencing.
A novel and efficient method to prepare amino acid thiohydantoins, which are required as reference standards for development of C-terminal protein sequencing, is reported. Amino acid thiohydantoins were prepared using a straightforward method involving reaction of 20 free amino acids with acetyl chloride as activating reagent and trimethylsilyl isothiocyanate (TMS-ITC) as derivatizing reagent. The products were characterized by HPLC, uv spectra, amino acid analysis, MS, and NMR. Different reaction conditions were investigated and the chemical mechanism of the formation of amino acid thiohydantoins was illustrated.
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Department of Biology, Hunan Normal University, Changsha, People's Republic of China.
Li
J
J
Liang
S
S
D000085:Acetates; D000596:Amino Acids / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D049148:Aminoacylation; D002712:Chlorides; D002851:Chromatography, High Pressure Liquid; D017879:Isothiocyanates; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011506:Proteins / Q000302:isolation & purification*; D017421:Sequence Analysis / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet; D013861:Thiocyanates; D013867:Thiohydantoins / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D014297:Trimethylsilyl Compounds
D000085:Acetates; D000596:Amino Acids; D002712:Chlorides; D017879:Isothiocyanates; D011506:Proteins; D013861:Thiocyanates; D013867:Thiohydantoins; D014297:Trimethylsilyl Compounds; C054796:trimethylsilylisothiocyanate; C026976:thiocyanic acid; C081124:acetyl chloride; C009941:potassium thiocyanate