3 -Deoxyadenosine cordycepin

A series of phospholipid conjugates of general structure (13) and (14) of AZT and 3 -deoxyadenosine (cordycepin) have been synthesised from the corresponding phosphoramidites (15) and (16). It is envisaged that they will act as prodrugs of the parent nucleoside monophosphates which possess enhanced membrane permeability. 

Scheme 59. Partial fragmentation of adenosine, 56, 2-deoxyadenoeine, 57 and 3-deoxyadenosine (cordycepin), 58.

Syntheses of the adenosine and guanosine 5 -phosphoroazidates (622) and (613), which were required as affinity labels, of P -di([ C]adenosine-5 )penta-phosphate, an inhibitor of adenylate kinase (E.C. 2.7.4.3), and, by improved procedures, of 3 -deoxyadenosine (cordycepin) 5 -triphosphate have been reported. 2 -Deoxy-2 -deuterio-adenosine (276) (see p. 100) and its 2 -epimer have been converted into the corresponding 3, 5 -phosphates, whose conformers were examined by H n.m.r. spectroscopy." ... 

Activation of the hydroxyl group in vitamin E, 35, to obtain vitamin E modified monomeric conjugates of 3 -deoxyadenosine (cordycepin), which inhibits HIV-1-induced syncytia formation, has been realized with diphosgene [30]. 

An improved 4-stage synthesis of 3 -deoxyadenosine (cordycepin) from adenosine has been described, giving a 38SK overall yield. (Scheme 3)... 

The biosynthesis of 3 -amino-3 -deoxyadenosine by Helminthosporium has been studied. As with the biosynthesis of 3 -deoxyadenosine (cordycepin), adenosine-... 

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