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2,2,4,6,7‐Pentamethyl‐2,3‐dihydrobenzofuran‐5‐methyl (Pbfm) as an Alternative to the Trityl Group for the Side‐Chain Protection of Cysteine and Asparagine/Glutamine
Author(s) -
Garcia Oscar,
Bofill Josep M.,
Nicolas Ernesto,
Albericio Fernando
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000201
Subject(s) - chemistry , protecting group , side chain , asparagine , cysteine , glutamine , residue (chemistry) , disulfide bond , derivative (finance) , stereochemistry , organic chemistry , combinatorial chemistry , amino acid , biochemistry , alkyl , financial economics , economics , enzyme , polymer
The benzyl derivative of the Pbf group, which is the most commonly used side‐chain protecting group for Arg, has been proposed for the protection of the side chains of Cys, Asp, and Glu. In the three cases, the new protecting group (Pbfm) was removed with a high concentration of TFA during the cleavage and global deprotection step. In addition, the Pbfm group can be removed from the Cys residue by using very dilute TFA solutions. Furthermore, when Cys is protected with the Pbfm group, it can be removed by oxidative treatment, thereby directly rendering the disulfide bridge on the solid phase.