Transglycosylation reactions of 6-thioguanine acyclonucleosides.
9-(2-Acetoxyethoxy)methyl-N2-acetyl-6-thoguanine (2) undergoes two different transglycosylation reactions: i) the 7<=>9 isomerization, which gives the respective 7-regioisomer (3) as the major product, ii) the 9<=>S6 glycosyl migration, which leads to a 9,S6-disubstituted product (4). S6-Methylation completely stopped the reversibility of transglycosylation.
Manikowski
A
A
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań.
Boryski
J
J
D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D013866:Thioguanine / Q000737:chemistry*
D009705:Nucleosides; D013866:Thioguanine