The oxidizing ability of benzo-dipteridine bearing a bipyridin-6-ylmethyl moiety (4) was found to be increased with Zn2+ by similar to 10(3)-fold for sulfite addition in MeOH and similar to 10(2)-fold for oxidation of an NADH model in MeCN. It was found for the first time that 4 is able to oxidize alpha -hydroxy acids to alpha -keto acids in the presence of a divalent metal ion such as Zn2+, Co2+, and Ni2+ and an amine base in MeCN or t-BuOH, whereas benzo-dipteridine having a bipyridin-5-ylmethyl moiety (3) is unable to oxidize them under the same conditions. The oxidation reaction was kinetically investigated including the kinetic isotope effect for deuterated mandelic acids (k(H)/k(D) = 2.1-3.7) and the Hammett plots for substituted mandelic acids (V-shaped plots). In the reaction of alpha -substituted alpha -hydroxy acids such as alpha -methyl mandelic and benzylic acids with 4, novel oxidative decarboxylation was found to take place, giving acetophenone and benzophenone, respectively. The oxidation mechanism for mandelic acid was proposed to proceed via a ternary complex of 4 . Zn2+. PhCH(OH)CO2-, in which alpha -oxyanion of mandelate attacks C(4a)-position of 4 to form an adduct followed by 1,2-elimination to afford benzoyl formate and 2e-reduced 4. The roles of the metal ion were proposed as follows; (i) activation of 4, (ii) substrate-binding site, and (iii) activation of the bound alpha -hydroxy acid by lowering pK(a)'s of alpha -OH and alpha -CH. This is a first example that a flavin model oxidizes alpha -hydroxy acids in the presence of a metal ion.