Synthesis of some S-3'-deoxyadenosyl-L-homocysteine analogues.
Condensation of 3'-deoxy-3-deazaadenosine, 3'-deoxy-7-deazaadenosine and 3'-deoxyadenosine with N,N'-bis-trifluoroacetyl-L-homocystine dimethyl ester and subsequent deprotection of the resulting N-trifluoroacetyl-S-3'-deoxyadenosyl-L-homocysteine analogues afforded S-3'-deoxy-3-deazaadenosyl-L-homocysteine, S-3'-deoxy-7-deazaadenosyl-L-homocysteine and S-3'-deoxyadenosyl-L-homocysteine respectively. 3'-Deoxy-3-deazaadenosine and 3'-deoxy-7-deazaadenosine were prepared by transformation of the corresponding ribonucleosides with 2-acetoxyisobutyryl bromide. 3'-Deoxy-7-deazaadenosine and 3'-deoxyadenosine were also converted into their 5'-chloro-3',5'-dideoxy derivatives which in turn were condensed with L-homocysteine sodium salt to give S-3'-deoxy-7-deazaadenosyl-L-homocysteine and S-3'-deoxyadenosyl-L-homocysteine which were identical with those synthesized by condensation of the protected L-homocystine with the 3'-deoxynucleosides.
D002855:Chromatography, Thin Layer; D006710:Homocysteine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012435:S-Adenosylhomocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D006710:Homocysteine; C051816:S-3'-deoxy-3-deazaadenosylhomocysteine; C051817:S-3'-deoxy-7-deazaadenosylhomocysteine; C051818:S-3'-deoxyadenosylhomocysteine; D012435:S-Adenosylhomocysteine