A chiral 5-deazaflavin derivative with 2-hydroxymethylphenyl group at
N(3) position of the pyrimidine ring has been synthesized. Oxidized fo
rm of the 5-deazaflavin derivative is reduced stereospecifically: the
hydroxymethyl group exerts steric inhibition in the absence of Mg2+, w
hereas it facilitates the approach of a reducing agent in the presence
of Mg2+.