Chemical- and cuticular phenoloxidase- mediated synthesis of cysteinyl-catechol adducts

Autor:	Manickam Sugumaran, Victor Semensi, Hemalata Dali
Rok vydání:	1989
Předmět:	chemistry.chemical_classification Catechol biology Physiology Chemistry Stereochemistry General Medicine biology.organism_classification Biochemistry Quinone Adduct Sarcophaga bullata chemistry.chemical_compound Enzyme Biosynthesis Covalent bond Insect Science Cysteine
Zdroj:	Archives of Insect Biochemistry and Physiology. 11:127-137
ISSN:	1520-6327 0739-4462
DOI:	10.1002/arch.940110206
Popis:	N-Acetylcysteine adducts of o-benzoquinones derived from catechol, 4-methylcatechol, and N-acetyldopamine were chemically synthesized and characterized by a combination of UV, IR, and NMR spectral studies. Oxidation of catechol, 4-methylcatechol, and N-acetyldopamine by cuticle-bound phenoloxidase from Sarcophaga bullata in the presence of N-acetylcysteine resulted in the formation of covalent adducts between catecholic compounds and N-acetylcysteine. Structural identities of these adducts were established by comparison of their HPLC retention time and UV spectra with those of synthetic adducts and by cochromatography with authentic samples. Although insect cuticle is known to contain only trace amounts of cysteine, the in vitro synthesis of quinone cysteine adducts mediated by cuticular phenoloxidase strongly indicates the occurrence of similar reactions in vivo as well and is in support of Pryor's quinone tanning hypothesis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::10d2373788bb7ad6a69178eea64c819c https://doi.org/10.1002/arch.940110206 Zobrazit plný text záznamu Plný text