Cysteine-S-trityl a key derivative to prepare N-methyl cysteines.
S-Trt Cys are used as precursors for the synthesis of protected NMe-Cys. N-Methylation of Alloc-Cys(Trt)-OH and Boc-Cys(Trt)-OH gives the corresponding N-methylated derivatives in good yields and purities, which can be further derivatized in solution to obtain a myriad of S-protected derivatives. To further broaden the scope of this methodology, the N (alpha)-amino protecting group of the NMe- S-protected Cys can be replaced easily either on the solid phase (from the Alloc precursor) or in solution (from the Boc precursor). Thus, this convenient route allows us to obtain many different protected NMe-Cys, which were of limited accessibility until now.
Marcucci
Eleonora
E
Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain. nuriabayo@gmail.com
Bayó-Puxan
Núria
N
Tulla-Puche
Judit
J
Spengler
Jan
J
Albericio
Fernando
F
D020650:Combinatorial Chemistry Techniques; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008745:Methylation; D008968:Molecular Conformation; D012996:Solutions
D012996:Solutions; C003724:3-tritylthio-L-alanine; D003545:Cysteine; C017507:mecysteine