Naslov
Transformations of Bioactive Peptides in the Presence of Sugars-Characterization and Stability Studies of the Adducts Generated via the Maillard Reaction

Autori
Roščić, Maja ; Horvat, Štefica

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 14 (2006); 4933-4943

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
glycation; Maillard; opioid; enkephalin; human serum; stability

Sažetak
Nonenzymatic glycation of leucine-enkephalin and related peptides by reducing sugars, has been studied for its potential role in the complications of diabetes. We present a previously undescribed nonenzymatic glycation pathway leading to stable imidazolidinone compounds in which C-1 of the aldohexose sugar moiety forms a bridge between the amino group of the N-terminal amino acid residue and the nitrogen of the adjacent peptide bond. Information concerning the enzymatic (human serum) and chemical stability of the imidazolidinone compounds obtained from glucose and leucine-enkephalin, endogenous opioid pentapeptide, and of its N-terminal fragments, is provided. All new imidazolidinone compounds exhibit high resistance against serum enzymes suggesting that the formation and persistance of glycated opioid peptides could contribute to the defective function of the endogenous opioid system during development of the diabetic syndrome.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA