7.8- Dihydropterin-6-carboxylates

Kuse, M., et al. (2001). 7,8-Dihydropterin-6-carboxylic acid as light emitter of luminous millipede, Luminodesmus sequoiae. Bioorg. Med. Chem. Lett. 11 1037-1040. 

Millipedes may show bioluminescence after molestation. The luminescent system of Luminodesmus sequoiae (now Motyxia sequoiae) is activated by ATP, magnesium, and molecular oxygen and involves a 104 kDa luciferase.193 Although the details of the mechanisms are unknown, it was concluded that 7,8-dihydropterin-6-carboxylic acid (141) is the light emitter.141 194... 

Satisfactory models are at hand for the 9a-chromophore, e.g. 7,8-dihydropterin-6-carboxylates, (27), which absorb around 400 nm. The lOa-chromophore, however, can at best be mimicked by a model which appears at first sight far-fetched, i. e. alloxane-dimethyl-aminoanil (72) cf. Scheme 13). But in fact 1-R-Fl-lOa-OOH is nothing but an or//2d -dialkylamino-anil of a 3,4-dihydro-alloxane. Such alloxane derivatives are well-known to have deep blue colours, max 600 nm 94,149). In fact we know such blue flavin derivatives, as will be outlined below. 

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