Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis.
Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5 min with mild reducing agents. S-Tmp is recommended for cysteine protection, as it yields crude peptides of high purity.
Institute for Research in Biomedicine, Barcelona, 08028, Spain.
Tobias M
TM
Postma
Matthieu
M
Giraud
Fernando
F
Albericio
D003545:Cysteine / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D010121:Oxytocin / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D004220:Disulfides; D010455:Peptides; D013438:Sulfhydryl Compounds; D010121:Oxytocin; D003545:Cysteine