58810-07-4Relevant academic research and scientific papers
Factors Influencing the Acid Lability of Substituted Arylsulphonyl Arginine Protecting Groups
Ali, Syed Safdar,Echner, Hartmut,Khan, Khalid Mohammed,Schroeder, Christoph,Hasan, Mashooda,et al.
, p. 1425 - 1433 (2007/10/02)
The kinetics of hydrolysis of new, NG-protected 2,4,6-triisopropylbenzene-sulphonyl (6), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (12) and phenanthrene-3-sulphonyl (17) Fmoc derivatives of L-arginine (1) in comparison with commercially available Fmoc-Arg(Mtr)-OH (Mtr = 4-methoxy-2,3,6-trimethyl-benzenesulphonyl (2)) are studied.The acid lability of the arylsulphonyl group is decreasing as follows Mtr > Tip > Mtbs > Phen.The effect of electron-donating alkyl groups as substituents in increasing the acid lability of the arylsulphonyl residue seems to be in the order of methyl > isopropyl > tert-butyl, while the effect of extended delocalization does not appreciably increase the acid lability. - Keywords: 2,4,6-Triisopropylbenzenesulphonyl (Tip), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (Mtbs), Phenanthrene-3-sulphonyl (Phen) Residues
The 2,4,6-Triisopropylbenzenesulfonyl Residue, a New Protecting Group for the Guanidino Function of Arginine
Echner, Hartmut,Voelter, Wolfgang
, p. 1591 - 1594 (2007/10/02)
The 2,4,6-triisopropylbenzenesulfonyl group is introduced in high yield into the guanidino function of arginine by the reaction of Nα-protected arginine with 2,4,6-triisopropylbenzenesulfonyl chloride.This protecting group was found to be cleaved by commonly used reagents used in peptide synthesis like methanesulfonic, trifluoromethanesulfonic acid or mixtures of trifluoroacetic with methanesulfonic or trifluoromethanesulfonic acid. - Keywords: Arginine Protecting Group, Arginine-Containing Peptides, Guanidino Function, Peptide Synthesis
