S-Homoadenosyl-l-cysteine and S-Homoadenosyl-l-homocysteine. Synthesis and Binding Studies of Non-Hydrolyzed Substrate Analogues with S-Adenosyl-l- …

RW Miles, LPC Nielsen, GJ Ewing, D Yin…

Index: Miles, Robert W.; Nielsen, Lars P. C.; Ewing, Gregory J.; Yin, Daniel; Borchardt, Ronald T.; Robins, Morris J. Journal of Organic Chemistry, 2002 , vol. 67, # 23 p. 8258 - 8260

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Citation Number: 14

Abstract

Treatment of homoadenosine [9-(5-deoxy-β-d-ribo-hexofuranosyl) adenine] with thionyl chloride and pyridine in acetonitrile gave 6'-chloro-6'-deoxyhomoadenosine, which underwent nucleophilic displacement with l-cysteine or l-homocysteine to give homologated analogues of S-adenosyl-l-homocysteine. Each amino acid in aqueous sodium hydroxide at 60° C gave excellent conversion from the chloronucleoside, and adsorption on Amberlite ...