Eritadenine is a chemical compound found in

shiitake The shiitake (alternate form shitake) (; ''Lentinula edodes'') is an edible mushroom native to East Asia, which is now cultivated and consumed around the globe. It is considered a medicinal mushroom in some forms of traditional medicine. T ...

mushrooms. Eritadenine is an inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH) and has hypocholesterolemic activity.

Synthesis

The structure is a purine alkylated with an oxidized sugar fragment. Eritadenine synthesis

Ring opening of the protected lactone (1), derived from

erythrose Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D -threose. Erythrose was first isolated in 1849 ...

with sodium phthalimide gives the acid 2; hydrazinolysis (cf

Gabriel synthesis The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel. The Gabriel reaction ...

) then leads to the amino acid 3. Displacement of chlorine in

pyrimidine Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The othe ...

4 by the amine function on 3 serves to attach the future imidazole nitrogen and the sugar-derived sidechain (5). The nitro group is then reduced by catalytic hydrogenation, the resulting primary amine is the most basic and is selectively formylated with

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est ...

. These strongly acidic conditions serve to remove the acetonide protecting group as well (6). Treatment with NaOH then serves to close the imidazole ring, forming eritadenine (7)

References

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External links

Structure and function of eritadenine and its 3-deaza analogues
Alkaloids Carboxylic acids