Nucleic acid related compounds, part 117.: S-homoadenosyl-L-cysteine and S-homoadenosyl-L-homocysteine.: Synthesis and binding studies of non-hydrolyzed substrate analogues with S-adenosyl-L-homocysteine hydrolase
Nucleic acid related compounds, part 117.: S-homoadenosyl-L-cysteine and S-homoadenosyl-L-homocysteine.: Synthesis and binding studies of non-hydrolyzed substrate analogues with S-adenosyl-L-homocysteine hydrolase
复制标题
DOI：
10.1021/jo020478g
复制
发表时间：
2002-11-15
影响因子：
3.6
通讯作者：
Robins, MJ
中科院分区：
文献类型：
--
作者：
Miles, RW;Nielsen, LPC;Robins, MJ
用乙腈中的亚硫酰氯和吡啶处理高腺苷[9-(5-脱氧-β-D-核糖-呋喃糖基)腺嘌呤]，得到6'-氯-6'-脱氧高腺苷，其与L-半胱氨酸或L-高半胱氨酸进行亲核置换，得到S-腺苷-L-高半胱氨酸的同系类似物。每种氨基酸在 60 ℃ 的氢氧化钠水溶液中都能从氯核苷中得到优异的转化，并且在 Amberlite XAD-4 树脂上的吸附比以前的方法提供了更方便的分离。观察到这些非水解类似物与 S-腺苷-L-高半胱氨酸水解酶的弱结合。
Treatment of homoadenosine [9-(5-deoxy-beta-D-ribo-hexofuranosyl)adenine] with thionyl chloride and pyridine in acetonitrile gave 6'-chloro-6'-deoxyhomoadenosine, which under-went 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 degreesC 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.