Pyrrolopyrimidine nucleosides

Two other pyrrolopyrimidine nucleoside antibiotics, mycalisines A and B (56,57), have been isolated from the sponge Mycale sp. (173). These bioactive marine metaboHtes inhibit cell division of starfish eggs. 

Uridine has been converted in seven steps into 5 -amino-3, 5 -dideoxyuridine (66), related to the 4, 5 -unsaturated structure found in the mureidomycin antibiotics. Some 5 -Amino-5 -deoxy-5-iodo-pyrrolopyrimidine nucleosides such as 67 (X = Cl, NH2) have been prepared by sodium salt glycosylation procedures, and shown to be powerful adenosine kinase inhibitors. ... 

On the basis of the sequenced a series of adjacent putative orfs comprising what appears to be a cluster of genes for the biosynthesis of the pyrrolopyrimidine nucleosides sangivamycin and toyocamycin, a pathway was proposed for the conversion of GTP to sangivamycin or toyocamycin, which is outlined in Figure 5.30b. 

Efficient routes have been described for the preparation of the 2,5 -anhydropyiiniidines 22, labelled with at C-2, 1 and the cyclic pyrrolopyrimidine nucleosides 23 have been prepared, with 5 -deoxy-5 -halogenonucleosides as intermediates. ... 

Table 4. Pyrrolopyrimidine, Diazepin, and Other A Nucleoside Antibiotics, Sugar-I -X...

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