10.1248/cpb.38.312
The research focuses on the development of functional biomimetic coenzyme models, specifically the synthesis of chiral 5-deazaflavin derivatives. The purpose of this study was to prepare new types of chiral deazaflavin derivatives that could effectively discriminate the enantiotopic faces of carbonyls in asymmetric reduction reactions, potentially serving as models for enzymatic systems. The researchers synthesized 5-deazaflavin derivatives with chiral substituents at the C(6) position and a chiral tertiary asymmetric carbon center at C(5). They used various chemicals in the process, including 8-chloro derivative, chiral primary amines such as (+)-dehydroabietylamine and (S)-(-)-phenylethylamine, dicyclohexylcarbodimide (DCC), and N-(tert-butoxycarbonyl)-L-valine.
10.1002/ardp.19903230203
The research investigates the addition of nucleophiles to 5-deazaflavins and 5-dedavinium salts, revealing a nicotinamide analogy in the addition of water, alcohols, metalorganic compounds, and amines at the 5-position of the 5-deazatavin structure. The study explores reactions with water and alcohols, finding that nucleophilic attack occurs at the 5-position, leading to the formation of various products, including ring-opening reactions in alkaline solutions. The research also examines the behavior of 5-deazaflavinium salts, which show different reactivity patterns compared to 5-deazaflavins, such as the formation of stable 5-adducts under certain conditions. Additionally, the study explores the reactions with metalorganic compounds, demonstrating the potential for synthesizing new C-substituted reduced 5-deazaflavins. The chemicals involved in the research include 5-deazaflavins, 5-dedavinium salts, various alcohols, metalorganic compounds like Grignard reagents, and amines. The study also involves the synthesis of several adducts and intermediates, such as 5-ethoxy, 5-ethyl, 5-benzyl, and other substituted 5-deazaflavin derivatives, which are characterized using spectroscopic methods.