Глутамиллизин

Description

Glutamylysine (L-α-glutamyl-L-lysine, γ-Glu-Lys) is a dipeptide formed by glutamic acid and lysine residues, formula C11H21N3O5, CAS 5891-53-2. Structural analogue of natural isopeptide cross-linking of proteins.

Basic Attributes

• CAS No: 5891-53-2
• Chemical formula: C11H21N3O5
• Molecular weight: 275.3; exact weight: 275.30
• DSSTox ID: DTXSID70558447
• HS code: 2924199090
• PSA: 156; XLogP3: 0.6684

Physico-chemical characteristics

• Density: 1.29 g/cm³
• Melting point: above 150 °C (with decomposition, solvent: methanol)
• Boiling point: 611.9 °C at 760 mm Hg. Art.
• Flash point: 323.9 °C
• Refractive index: 1.538
• Storage conditions: -15 °C

Biochemical significance and application

The class of substance is a dipeptide that connects glutamic acid and lysine residues with an amide bond. A related structure, the isopeptide (γ-glutamyl-ε-lysine) cross-link, is formed in proteins by transglutaminase enzymes that catalyze the connection between the γ-carboxamide group of glutamine and the ε-amino group of lysine; such cross-links form stable covalent bonds in the structural proteins of the skin, hair, as well as in the process of blood clotting (factor XIII stabilizes the fibrin clot precisely through such bonds). The free dipeptide glutamylysine is used as a reference compound and biochemical marker in the study of transglutaminase activity and degradation of cross-linked proteins, as well as in cosmetic formulations claiming to maintain skin health and elasticity.

Storage and transportation

Store at -15 °C, in an airtight container, protected from moisture and light - like other peptides, the substance is sensitive to hydrolysis and oxidative destruction when stored under unfavorable conditions.

The importance of isopeptide cross-links in protein biology

Transglutaminase enzymes are widely distributed in animal tissues and are involved in blood coagulation, structuring of skin and hair, formation of the extracellular matrix, apoptotic cell stabilization and construction of protective epithelial barriers. γ-glutamyl-ε-lysine cross-links are extremely resistant to proteolytic degradation by conventional digestive enzymes, and their accumulation or deficiency is considered a biomarker for a number of pathological processes, including bleeding disorders and skin diseases.

Identification and patent mentions

In the patent literature, sequence fragments containing glutamylysine residues are referred to as claimed protein sequences (eg, WO2005081628, WO2011146121, WO2018204847), reflecting the interest in this structural motif in biotechnological development.

The role of transglutaminases in physiology

Transglutaminase enzymes are widely distributed in animal tissues and catalyze γ-glutamyl-ε-lysine cross-linking during blood coagulation, extracellular matrix formation, apoptotic cell stabilization and the construction of protective epithelial barriers - therefore, measuring the content of free and bound glutamyl-lysine in tissues serves as a biomarker of the activity of these physiological processes.