Potentielle Cytostatica, 6. Konfiguration und Derivate von 1‐Methylamino‐1‐desoxy‐zuckeralkoholen aus Aldohexosen und Aldopentosen

Dorn, Helmut; Welfle, Heinz; Liebig, R.

doi:10.1002/cber.19660990314

Cited by 16 publications

(1 citation statement)

References 19 publications

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“…To investigate this hypothesis, the N -methylated analogue 32 was synthesized (Scheme ). Substitution of 6-chloro-5-nitro-2,4-dimethoxypyrimidine ( 29 ) with methylribitylamine ( 28 ), followed by deprotection of intermediate 30 , gave nitro compound 31 . Compound 31 was reduced by catalytic hydrogenation in the presence of hydrochloric acid to give amino compound 32 .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Acyclic C-Nucleoside and N-Methylated Derivatives of the Ribitylaminopyrimidine Substrate of Lumazine Synthase as Potential Enzyme Inhibitors and Mechanistic Probes

et al. 2004

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Lumazine synthase and riboflavin synthase catalyze the last two steps in the biosynthesis of riboflavin, a vitamin that is involved in many critical biochemical reactions that are essential for the maintenance of life. To obtain inhibitors and structural probes that could be useful in studying the structures of bound reaction intermediates, the ribitylamino N-H moiety of the lumazine synthase substrate was replaced by CH(2) and N-CH(3) groups. The CH(2) replacement unexpectedly and completely abolished the affinity for lumazine synthase, thus revealing a critical, yet unexplained, role of the ribitylamino N-H moiety in conferring affinity for the enzyme. In contrast, the N-CH(3) replacement resulted in an inhibitor of both lumazine synthase and riboflavin synthase. Replacement of the ribitylamino N-H moiety with epimeric C-F moieties led to inhibition of lumazine synthase and riboflavin synthase when combined with the replacement of the 5-amino group with a nitro substituent.

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Section: Resultsmentioning

confidence: 99%