Menaquinone Biosynthesis: The Mechanism of 5,8-Dihydroxy-2-naphthoate Synthase (MqnD),Biochemistry

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Menaquinone Biosynthesis: The Mechanism of 5,8-Dihydroxy-2-naphthoate Synthase (MqnD)
Biochemistry ( IF 2.9 ) Pub Date : 2021-06-18 , DOI: 10.1021/acs.biochem.1c00257
Hannah R Manion-Sommerhalter ₁ , Dmytro Fedoseyenko ₁ , Sumedh Joshi ₁ , Tadhg P Begley ₁

Affiliation

MqnD catalyzes the conversion of cyclic dehypoxanthine futalosine (6) to 5,8-dihydroxy-2-naphthoic acid (7) and an uncharacterized product. This study describes a chemoenzymatic synthesis of 6. This synthesis achieved a 2-fold yield enhancement by using titanium(III) citrate as the reducing agent and another 5-fold yield enhancement using a fluorinated analogue of dehypoxanthine futalosine (5) that was converted to 6 by an ipso substitution mechanism. This synthetic route enabled the synthesis of 6 in sufficient quantity to identify the second reaction product and to determine that the MqnD-catalyzed reaction proceeds by a hemiacetal ring opening–tautomerization–retroaldol sequence.

中文翻译：

甲基萘醌生物合成：5,8-二羟基-2-萘甲酸合酶 (MqnD) 的机制

MqnD 催化环状脱次黄嘌呤二氢呋喃 ( 6 ) 向 5,8-二羟基-2-萘甲酸 ( 7 ) 和未表征的产物的转化。本研究描述了6的化学酶促合成。通过使用柠檬酸钛 (III) 作为还原剂，该合成实现了 2 倍的产率提高，并使用通过 ipso取代机制转化为6的脱次黄嘌呤 futalosine ( 5 )的氟化类似物将产率提高了 5 倍。该合成路线能够合成足够数量的6以鉴定第二个反应产物，并确定 MqnD 催化的反应通过半缩醛开环-互变异构化-逆羟醛序列进行。

更新日期：2021-06-29

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