387868-34-0

Basic information

• Product Name: H-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH
• Synonyms: H-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH;H-PEN(MEOBZL)-OH;H-PEN(PMEOBZL)-OH;S-4-METHOXYBENZYL-L-PENICILLAMINE;S-P-METHOXYBENZYL-3,3-DIMETHYL-L-CYSTEINE;S-P-METHOXYBENZYL-L-PENICILAMINE;H-β,β-Dimethyl-L-Cys(pMeOBzl)-OH;L-Pen(pMeOBzl)-OH
• CAS NO: 387868-34-0
• Molecular Formula: C₁₃H₁₉NO₃S
• Molecular Weight: 269.36
• Mol File: 387868-34-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 2-8°C
• CAS DataBase Reference: H-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH(387868-34-0)
• EPA Substance Registry System: H-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH(387868-34-0)

Safety Data

• Hazardous Substances Data: 387868-34-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

S-4-Methoxybenzyl-L-penicillamine is used in the synthesis of peptidic-ligands as catalyst for biomimetic nitrile hydration.

Upstream product

• 1113-41-3 L-penicillamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 120944-75-4 N-tertbutyloxycarbonyl-S-p-methoxybenzyl-L-penicillamine 

Relevant articles and documents

Bio-inspired nitrile hydration by peptidic ligands based on L-cysteine, L-methionine or L-penicillamine and pyridine-2,6-dicarboxylic acid

Nitrile hydratase (NHase, EC 4.2.1.84) is a metalloenzyme which catalyses the conversion of nitriles to amides. The high efficiency and broad substrate range of NHase have led to the successful application of this enzyme as a biocatalyst in the industrial syntheses of acrylamide and nicotinamide and in the bioremediation of nitrile waste. Crystal structures of both cobalt(III)- and iron(III)-dependent NHases reveal an unusual metal binding motif made up from six sequential amino acids and comprising two amide nitrogens from the peptide backbone and three cysteine-derived sulfur ligands, each at a different oxidation state (thiolate, sulfenate and sulfinate). Based on the active site geometry revealed by these crystal structures, we have designed a series of small-molecule ligands which integrate essential features of the NHase metal binding motif into a readily accessible peptide environment. We report the synthesis of ligands based on a pyridine-2,6-dicarboxylic acid scaffold and L-cysteine, L- S-methylcysteine, L-methionine or L-penicillamine. These ligands have been combined with cobalt(III) and iron(III) and tested as catalysts for biomimetic nitrile hydration. The highest levels of activity are observed with the L-penicillamine ligand which, in combination with cobalt(III), converts acetonitrile to acetamide at 1.25 turnovers and benzonitrile to benzamide at 1.20 turnovers.