Premium
Tmob Side Chain‐protected S ‐Cysteine‐ and homo‐ S ‐Cysteinesulfonamides, their N α ‐Protected and N ω ‐Aminoethylated Derivatives
Author(s) -
Videnov Georgi,
Aleksiev Boris,
Stoev Mincho,
Paipanova Tamara,
Jung Günther
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301150
Subject(s) - chemistry , cysteine , protecting group , derivatization , enantiomer , bacillus subtilis , cysteine protease , peptide , side chain , group (periodic table) , racemic mixture , stereochemistry , amino acid , resolution (logic) , organic chemistry , enzyme , biochemistry , high performance liquid chromatography , biology , bacteria , computer science , genetics , polymer , alkyl , artificial intelligence
The 2,4,6‐trimethoxybenzyl (Tmob) group is very suitable for temporary protection of the aminosulfonyl group of S ‐cysteine‐ and homo‐ S ‐cysteinesulfonamides. Both the introduction and removal of the Tmob‐protecting group can be achieved in high yields. 2‐Aminoethyl derivatization of the aminosulfonyl group of S ‐cysteine‐ and homo‐ S ‐cysteinesulfonamides has been carried out, and various derivatives useful for peptide synthesis with Z, Boc and Fmoc as N α ‐protecting groups have been prepared. In all cases, a racemic mixture of S ‐cysteine‐ or homo‐ S ‐cysteinesulfonic acid has been used and subsequent enantiomer resolution has been achieved by treatment with Bacillus subtilis alkaline protease.