Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase
Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase
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DOI：
10.1016/j.bmcl.2004.02.039
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发表时间：
2004-05-03
影响因子：
2.7
通讯作者：
Jeong, LS
中科院分区：
文献类型：
--
作者：
Kim, HO;Yoo, SJ;Jeong, LS
使用亲电氟化作为关键步骤，由 D-环戊烯酮衍生物 5 高效合成 Fluoro-DHCeA (4)。 Fluoro-DHCeA (4) 被发现与 DHCeA (3) 一样有效，但与显示可逆抑制的 DHCeA (3) 不同，它表现出不可逆的酶抑制作用。根据这项研究，neplanocin A 和氟-neplanocin A 的 4'-羟甲基在与酶活性位点的结合中发挥着重要作用。 (C) 2004 Elsevier Ltd. 保留所有权利。
Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this Study, 4'-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.