Regiospecific synthesis of 3,5-bis(bromomethyl)benzoic acid, a cysteine crosslinking agent

Add time:08/13/2019    Source:sciencedirect.com

Bridging two molecules of an organic thiol with the 3,5-dimethylenebenzoic acid (Dmb) group produces a rigid five-carbon Dmb crosslink that is stable to disulfide reducing agents. Radical bromination of 3,5-dimethylbenzoic acid or its succinimido ester gave four α-brominated products. So NMR-pure 3,5-bis(bromomethyl)benzoic acid (Br2Dmb) was regiospecifically synthesized in 38% overall yield by a four-step route from 1,3,5-benzenetricarboxylic acid. S-Alkylation of cysteine methyl ester, a model thiol, with Br2Dmb provided the 2:1 adduct (Cys-OCH3)2 Dmb in 79% yield. Subsequent N-protection with di(tert-butyl) dicarbonate gave (Boc-Cys-OCH3)2Dmb in 60% overall yield from cysteine methyl ester. This protected diamino acid is suitable for assembly of two Dmb-crosslinked peptide chains.

We also recommend Trading Suppliers and Manufacturers of 4-(2-Aminoethyl)benzoic acid tert-butyl ester (cas 135482-70-1). Pls Click Website Link as below: cas 135482-70-1 suppliers

Prev:Research paper4-Hydroxy-1,2,3-triazole moiety as bioisostere of the carboxylic acid function: a novel scaffold to probe the orthosteric γ-aminobutyric acid receptor binding site
Next:Research paperStructure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold)