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 |
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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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