An Fe2+ - and α-Ketoglutarate-Dependent Halogenase Acts on Nucleotide Substrates.,Angewandte Chemie International Edition

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An Fe2+ - and α-Ketoglutarate-Dependent Halogenase Acts on Nucleotide Substrates.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-03-11 , DOI: 10.1002/anie.201914994
Chunhua Zhao ₁ , Shan Yan ₁ , Qin Li ₁ , Hucheng Zhu ₁ , Zhiyu Zhong ₂ , Ying Ye ₁ , Zixin Deng ₂ , Yonghui Zhang ₁

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While halogenated nucleosides are used as common anticancer and antiviral drugs, naturally occurring halogenated nucleosides are rare. Adechlorin (ade) is a 2′‐chloro nucleoside natural product first identified from Actinomadura sp. ATCC 39365. However, the installation of chlorine in the ade biosynthetic pathway remains elusive. Reported herein is a Fe²⁺‐α‐ketoglutarate halogenase AdeV that can install a chlorine atom at the C2′ position of 2′‐deoxyadenosine monophosphate to afford 2′‐chloro‐2′‐deoxyadenosine monophosphate. Furthermore, 2′,3′‐dideoxyadenosine‐5′‐monophosphate and 2′‐deoxyinosine‐5′‐monophosphate can also be converted, albeit 20‐fold and 2‐fold, respectively, less efficiently relative to the conversion of 2′‐deoxyadenosine monophosphate. AdeV represents the first example of a Fe²⁺‐α‐ketoglutarate‐dependent halogenase that converts nucleotides into chlorinated analogues.

中文翻译：

Fe2 +和α-酮戊二酸依赖性卤素酶作用于核苷酸底物。

尽管卤代核苷被用作常见的抗癌和抗病毒药物，但天然存在的卤代核苷很少见。脱除二氯（ade）是2'-氯核苷天然产物，最初从Actinomadura sp。鉴定。ATCC39365。但是，在ade生物合成途径中安装氯气仍然难以实现。本文报道的是Fe ²⁺-α-酮戊二酸卤化酶AdeV可以在2'-脱氧腺苷单磷酸的C2'位置安装一个氯原子，得到2'-氯-2'-脱氧腺苷单磷酸。此外，2'，3'-二脱氧腺苷-5'-单磷酸酯和2'-脱氧肌苷-5'-单磷酸酯的转化效率相对于2'-转化率分别降低了20倍和2倍。脱氧腺苷一磷酸。AdeV代表Fe 2 ⁺ -α-酮戊二酸依赖性卤化酶的第一个实例，该酶将核苷酸转化为氯化类似物。

更新日期：2020-03-11

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