Chemical synthesis and spontaneous glycosidic hydrolysis of 3-methyl-2'-deoxyguanosine and 2'-deoxywyosine [1].
3-methyl-2'-deoxyguanosine (1a) is obtained from 2'-deoxyguanosine by a reaction sequence involving conversion into tricyclic 1,N-2-isopropeno derivative (4-desmethyl-2'-deoxywyosine, 3a) followed by methylation which results in 2'-deoxywyosine (2a) and final removal of the 1,N-2 blocking system. Compounds 1a and 2a undergo spontaneous hydrolytic cleavage of their glycosidic bonds at pH 7, 37 degrees C, which makes them the most labile of all known nucleosides composed of structural units occurring in nature.
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan.
B
B
Golankiewicz
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T
Ostrowski
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W
Folkman
D055598:Chemical Phenomena; D002621:Chemistry; D002845:Chromatography; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D006027:Glycosides / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure
D006027:Glycosides; C065644:2'-deoxywyosine; C065645:3-methyl-2'-deoxyguanosine; D003849:Deoxyguanosine