S-Homoadenosyl-l-cysteine and S-Homoadenosyl-l-homocysteine. Synthesis and Binding Studies of Non-Hydrolyzed Substrate Analogues with S-Adenosyl-l-homocysteine Hydrolase1

Autor: Robert W. Miles, Dan Yin, Morris J. Robins, Gregory J. Ewing, Lars P. C. Nielsen, Ronald T. Borchardt
Rok vydání: 2002
Předmět:
Zdroj: The Journal of Organic Chemistry. 67:8258-8260
ISSN: 1520-6904
0022-3263
DOI: 10.1021/jo020478g
Popis: 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 XAD-4 resin provided more convenient isolation than prior methods. Weak binding of these non-hydrolyzed analogues to S-adenosyl-l-homocysteine hydrolase was observed.
Databáze: OpenAIRE
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