118527-62-1Relevant articles and documents
Synthesis of Queuine, the Base of Naturally Occuring Hypermodified Nucleoside (Queuosine), and Its Analogues
Akimoto, Hiroshi,Imamiya, Eiko,Hitaka, Takenori,Nomura, Hiroaki,Nishimura, Susumu
, p. 1637 - 1644 (2007/10/02)
A convenient new method for synthesizing queuine (1) pyrrolopyrimidin-4(3H)-one>, the base of the naturally occuring hypermodified nucleoside, queuosine, present in certain transfer RNAs, and its biosynthetic precursor, 2-amino-5-aminomethylpyrrolopyrimidin-4(3H)-one (2) (Pre Q1 base), was succesfully exploited.This method involved two critical rections: the Mannich reaction using dibenzylamine-formaldehyde of 2-acrylaminopyrrolopyrimidin-4(3H)-one (7), which resulted in the selective introduction of the dibenzylaminomethyl group into the 5-position of (7), and an amine exchange reaction of the 5-dibenzylamino function in the resulting Mannich base (17) with (1S,2R,3S)-2,3-isopropylidenedioxycyclopent-4-enylamine, which yielded the desired queuine (1).Similar reaction of (17) with ammonia gave the biosynthetic precursor of queuine (2) (Pre Q1 base).Thus, a series of queuine analogues with structural variations in their 5-aminomethyl side-chains was synthesized by the amine exchange reaction of (17) with appropriate amines or by acylation of (2) with appropriate acylating agents.
