Cysteine from WACKER - Wacker Chemie AG


Cysteine from WACKER

WACKER has developed a more efficient method for producing L-cysteine. This consists in generating the amino acid with the aid of bacterial fermentation. Cysteine products from WACKER are vegetarian, kosher and halal grade. They conform to all important food and pharmaceutical quality standards.

Chemical Definition

L-Cysteine is one of the 20 natural amino acids and is the only one that contains a sulfhydryl group (– SH) in the side chain . This is highly chemically reactive and forms disulfide bridges which lend proteins much of their stability

and are responsible, for example, for the strong fiber strands of hair, wool, feathers, nails, hooves and horn. A large proportion of the keratins, i.e. the protein, in these materials consists of cysteine.

Production of Cysteine at WACKER

L-Cysteine is traditionally produced industrially from animal products, such as feathers or hair, by boiling out with hydrochloric acid. WACKER has developed a biotechnical process for this and taken out several patents on it. The amino acid is obtained by fermentation of glucose and inorganic salts.

The actual work of synthesis is performed by metabolically optimized bacteria (Escherichia coli). The metabolism of the bacteria was modified by biomolecular intervention to induce them to produce

  • much more L-cysteinethan they actually need for themselves, and to
  • excrete the synthesized L-cysteine into the nutrient broth.

This "metabolic engineering" did not involve integrating foreign genes into the bacteria.

L-Cysteine products from WACKER are vegetarian, kosher and halal grade. They conform to all important food and pharmaceutical quality standards, such as the EP, EU Directive 2000/63/EC, USP, JP and FCC. WACKER ensures maximum purity according to FCC and EP through the implementation of a comprehensive quality management system during production.

Applications for Cysteine

L-Cysteine is highly versatile:

  • It can break disulfide bridges in peptides and proteins.
  • It acts as a radical scavenger.
  • It can be used as a reducing agent .

By virtue of these properties, L-cysteine from WACKER can be used in various areas, especially life sciences. It is used especially in the industrial segments of pharma, cosmetics, food and dietary supplements .

Cysteine in the Food Industry

In food applications, L-cysteine is the ideal intermediate for process flavorings. It is principally used in meat flavorings and roast aromas. L-Cysteine is added to various types of dough during processing to break down the gluten, a sticky protein contained in flour. This makes the dough much easier to knead and process.

Cysteine in the Pharmaceutical Industry

In the pharmaceutical sector, the primary use of L-cysteine is as starter material for the production of the cysteine derivatives N-acetyl-L-cysteine and S-(carboxymethyl)-L-cysteine. Both derivatives serve therapeutic uses as mucolytics. The SH groups are formed in vivo in the case of S-(carboxymethyl)-L-cysteine. They destroy the disulfide bridges of proteinsin bronchial phlegm and lower its viscosity.

Of late, N-acetyl-L-cysteine is also being used as a nutraceutical, especially on the U.S. market. As L-cysteine raises the glutathione level, it boosts redox activity, especially in the liver.

L-cysteine also serves as a processing auxiliary for refolding genetically engineered protein active molecules, e.g. in the production of human insulin. This application, too, is based on the capability of the SH-groups to break incorrectly formed disulfide bridges – but in this case to form them correctly again subsequently.

Moreover, L-cysteine is used in the pharma industry as a building block for protein and peptide actives. The customers are companies that produce amino acids that are protected at first, and are subsequently used in peptide synthesis.

In medical diagnostics, cysteine functions as a component of nutrients, e.g. agar plates and nutrient broths used for cultivating bacteria.

Cysteine in the Cosmetics Industry

In some cosmetic preparations, L-cysteine is used as an antiaging agent. This application makes use of cysteine's property of acting as a radical scavenger. The amino acid can therefore contribute to delaying aging processes, for example of the skin.

Especially, in Japan, L-cysteine is used to prepare hair for permanent waves, instead of the unpleasant smelling thioglycolic acid that is preferred in Europe. It dissolves the disulfide bridges of the keratin in the hair, loosening the hair structure and reshaping the hair.

Find out more about L-cysteine from WACKER in unserer Produktübersicht.

At a Glance

L-Cysteine is traditionally produced industrially from animal products, such as feathers or hair, by boiling out with hydrochloric acid. WACKER has developed a biotechnical process for manufacturing L-cysteine, in which the amino acid is obtained by fermentation from glucose and inorganic salts. The actual work of synthesis is performed by metabolically optimized bacterial (Escherichia coli). By selective biomolecular intervention in the metabolism of the bacteria, they were modified, first, to produce far more L-cysteine than they need for themselves, and, second, to excrete the synthesized L-cysteine into the nutrient broth. This "metabolic engineering" did not involve integrating foreign genes into the bacteria. WACKER holds several patents on the process. L-Cysteine products from WACKER are vegetarian, kosher and halal grade. They conform to all important food and pharmaceutical quality standards, such as the EP, EU Directive 2000/63/EC, USP, JP and FCC. In the production of L-cysteine, a high GMP standard and comprehensive quality management ensure maximum purity according to FCC and EP. L-Cysteine can be used in a variety of applications, in particular in life science applications, and also permit kosher and halal applications in the food sector.

L-Cysteine is characterized by a versatile range of properties: It can break disulfide bridges in peptides and proteins, acts as a radical scavenger and can be used as reducing agent. These properties give L-cysteine a wide range of uses, particularly in the pharmaceutical, cosmetic, food and food supplement sectors.

In food applications, L-cysteine is the ideal intermediate for process flavorings and is principally used in meat flavorings and roast aromas. L-Cysteine is added to various types of dough during processing to break down the gluten, a sticky protein contained in flour. This makes the dough much easier to knead and process.

In the pharmaceutical sector, the primary economic use of L-cysteine is as starter material for the production of the cysteine derivatives N-acetyl-L-cysteine and S-(carboxymethyl)-L-cysteine. Both derivatives serve therapeutic uses as mucolytics. The SH groups, formed in vivo in the case of S-(carboxymethyl)-L-cysteine, destroy the disulfide bridges of proteins in bronchial phlegm and lower its viscosity. Of late, N-acetyl-L-cysteine is also being used as a nutraceutical, especially on the U.S. market. This application is based on the fact that L-cysteine raises the glutathione level and consequently boosts redox activity, especially in the liver.

Second place in pharmaceutical application goes to the use of L-cysteine as a processing auxiliary for refolding genetically manufactured protein active molecules. In this function, the amino acid is used, e.g., in the the production of human insulin. This application, too, is based on the capability of the SH-groups to break incorrectly formed disulfide bridges – but in this case to form them correctly again subsequently.

Moreover, L-cysteine is used in the pharma industry as a building block for protein and peptide actives. The customers are companies that produce amino acids that are protected at first, and are subsequently used in peptide synthesis.

This amino acid is finally used in an entirely different field of life sciences, namely medical diagnostics. Here, it functions as a component of nutrients, e.g. agar plates and nutrient broths used for cultivating bacteria.

More recently, L-cysteine is also increasingly being used in the cosmetics industry. In some cosmetic preparations, the amino acid is used as an antiaging agent. This application makes use of L-cysteine's property of acting as a radical scavenger. The amino acid can therefore contribute to delaying aging processes – for example of the skin. A second application from the field of cosmetics is principally the Japanese market: In Japan, L-cysteine is used instead of the malodorous thioglycolic acid preferred in Europe to prepare hair for permanent waves. It dissolves the disulfide bridges of the keratin in the hair, loosening the hair structure and reshaping the hair.

Of the twenty natural amino acids, cysteine is the only one to contain a sulfhydryl group (thiol group –SH) in its side chain. This is highly chemically reactive and can thereby form disulfide bridges which lend proteins much of their stability (This is responsible, for example, for the strength in strands of hair, wool, feathers, nails, hooves and horns. A large proportion of the proteins, keratins, in these materials comprises cysteine.)