9-(Aminoalkyl)-8-hydroxyadenines: Preparation, mechanism of formation and use in affinity chromatography of S-adenosyl-L-homocysteine hydrolase

Autor:	Jitka Kohoutová, Antonín Holý, Aleš Merta, Ivan Votruba
Rok vydání:	1986
Předmět:	Affinity chromatography Stereochemistry Chemistry S-adenosyl-L-homocysteine hydrolase General Chemistry
Zdroj:	Collection of Czechoslovak Chemical Communications. 51:459-477
ISSN:	1212-6950 0010-0765
DOI:	10.1135/cccc19860459
Popis:	Bromine reacts with 9-(2-hydroxyethyl)- (Va), 9-(3-hydroxypropyl)- (Vb), 9-(2-hydroxypropyl)- (Vc), 9-(2,3-dihydroxypropyl)- (Vd), 9-(1,3-dihydroxy-2-propyl)- (Ve), 9-threo-(2,3-dihydroxybutyl)- (Vf) and 9-threo-(2,3,4-trihydroxybutyl)adenine (Vg) to give 8-bromoadenine derivatives (Vl). Reaction of compounds Vl with ammonia results in intramolecular cyclization to five- and six-membered cyclic esters which are regiospecifically opened to afford the respective 2-amino-alkyl-8-hydroxyadenines (VIIa, b) and 3-aminoalkyl-8-hydroxyadenines (VIIc-VIIf). Binding of compounds VII to CH-Sepharose 4B led to the polymeric material XIII capable of binding S-adenosyl-L-homocysteine hydrolase. Compounds XIII derived from the amino derivatives VIIa, b, d are of affinity support character and liberate the enzyme only on elution with dilute adenosine solution.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cdefd98a480a70c1b57d28d050020bb0 https://doi.org/10.1135/cccc19860459 Zobrazit plný text záznamu