The effect of peptide length on the cleavage kinetics of 2-chlorotrityl resin-bound ethers.
Different characteristics of cleavage kinetics of resin-bound amino alcohols and their peptide derivatives were observed in acid containing protic and aprotic solvent mixtures. The hydrolysis reactions are hindered by steric crowding around the cleaving C--O bond and accelerated by the special solvation effect of CF(3)CH(2)OH on the peptide chain as well as the increase of the strength and concentration of the acid. In trifluoroacetic acid containing mixtures, trifluoroacetylation of the peptide alcohols was detected. The appearance of O-trifluoroacetyl serine and threonine derivatives is detected in cleavage mixtures containing trifluoroacetic acid in anhydrous solvent.
Kocsis
László
L
Research Group of Peptide Chemistry at Eötvös Loránd University, Hungarian Academy of Sciences, Budapest 112, Hungary.
Ruff
Ferenc
F
Orosz
György
G
D000107:Acetylation; D000596:Amino Acids / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004987:Ethers / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry; D006860:Hydrogen Bonding; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry*; D012116:Resins, Plant / Q000737:chemistry*; D013816:Thermodynamics; D014269:Trifluoroacetic Acid / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
D000596:Amino Acids; D000605:Amino Alcohols; D004987:Ethers; D005449:Fluorenes; D010455:Peptides; D012116:Resins, Plant; D014320:Triphenylmethyl Compounds; C071065:2-chlorotrityl chloride; D014269:Trifluoroacetic Acid