79590-29-7Relevant academic research and scientific papers
Method for protecting guanidino group and restoring the same
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, (2008/06/13)
A guanidino group in an amino acid or a peptide can be protected with a specific group, i.e. pentamethylbenzensulfonyl, 2,4,6-trimethoxybenzenesulfonyl, 4-methoxy-2,3,5,6-tetramethylbenzenesulfonyl, 4-methoxy-2,6-dimethylbenzenesulfonyl or 4-methoxy-2,3,6-trimethylbenzenesulfonyl, and said group may easily be removed without affecting the amino acid or the peptide to be derived from the protected amino acid or peptide. Thus, the present invention is useful in the synthesis of peptides containing the guanidino group.
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
