Protection of the amino group of adenosine and guanosine derivatives by elaboration into a 2,5-dimethylpyrrole moiety.
[reaction: see text] Protection of the amino group of adenine and guanine nucleosides was effected by heating the substrates in 2,5-hexanedione. The resulting 2,5-dimethylpyrrole adducts were stable toward bases but were hydrolyzed with TFA/H(2)O to regenerate the amino function.
Nowak
Ireneusz
I
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Robins
Morris J
MJ
D000241:Adenosine / Q000031:analogs & derivatives*; D006151:Guanosine / Q000031:analogs & derivatives*; D006588:Hexanones / Q000737:chemistry; D006358:Hot Temperature; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry / Q000378:metabolism; D011758:Pyrroles / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014269:Trifluoroacetic Acid / Q000737:chemistry; D014867:Water / Q000737:chemistry
D006588:Hexanones; D009705:Nucleosides; D011758:Pyrroles; D014867:Water; D006151:Guanosine; C011269:2,5-hexanedione; D014269:Trifluoroacetic Acid; D000241:Adenosine; C067286:2,5-dimethylpyrrole