75806-97-2Relevant academic research and scientific papers
Further Studies on the Use of Multi-substituted Benzenesulfonyl Groups for Protection of the Guanidino Function of Arginine
Fujino, Masahiko,Wakimasu, Mitsuhiro,Kitada, Chieko
, p. 2825 - 2831 (2007/10/02)
Various multi-substituted benzenesulfonyl protecting groups for the guanidino function of arginine, removable under mild conditions such as with trifluoroacetic acid (TFA)-thioanisole, were studied.Among them, the 4-methoxy-2,6-dimethylbenzenesulfonyl (Mds) group, the 2,3,4,5,6-pentamethylbenzenesulfonyl (Pme) group, and the 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr) group were found to be useful.Both Mds and Pme show considerable resistance to TFA and, therefore, are suitable for procedures in which the intermediates are deprotected by TFA treatment, while Mtr is the most useful protecting group when TFA treatment is not necessary.Keywords---4-methoxy-2,6-dimethylbenzenesulfonyl (Mds); 2,4,6-trimethoxybenzenesulfonyl (Mtb); 2,3,4,5,6-pentamethylbenzenesulfonyl (Pme); 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr); trifluoroacetic acid-thioanisole deprotection
4-Methoxy-2,6-dimethylbenzenesulphonyl (Mds): a New Protecting Group of the Guanidino Function in Peptide Synthesis
Fujino, Masahiko,Nishimura, Osamu,Wakimasu, Mitsuhiro,Kitada, Chieko
, p. 668 - 669 (2007/10/02)
The 4-methoxy-2,6-dimethylbenzenesulphonyl (Mds) group for the protection of the guanidino function, which is readily removed with trifluoroacetic acid-thioanisole but is resistant to hydrogenolysis or treatment with dilute hydrogen chloride, can be used in the solution synthesis of arginine-containing peptides; this protecting group was effectively used in the synthesis of substance P and two LH-RH analogues.
