在麦角硫因和卵巯肽生物合成中氧化 C-S 键形成的区域选择性。
Regioselectivity of the oxidative C-S bond formation in ergothioneine and ovothiol biosyntheses.
机构信息
Department of Chemistry, Boston University , Boston, Massachusetts 02215, United States.
出版信息
Org Lett. 2013 Sep 20;15(18):4854-7. doi: 10.1021/ol402275t. Epub 2013 Sep 9.
Abstract
Ergothioneine (5) and ovothiol (8) are two novel thiol-containing natural products. Their C-S bonds are formed by oxidative coupling reactions catalyzed by EgtB and OvoA enzymes, respectively. In this work, it was discovered that in addition to catalyzing the oxidative coupling between histidine and cysteine (1 → 6 conversion), OvoA can also catalyze a direct oxidative coupling between hercynine (2) and cysteine (2 → 4 conversion), which can shorten the ergothioneine biosynthetic pathway by two steps.
摘要
ergothioneine (5) 和 ovothiol (8) 是两种新型含硫天然产物。它们的 C-S 键分别由 EgtB 和 OvoA 酶催化的氧化偶联反应形成。在这项工作中，发现除了催化组氨酸和半胱氨酸之间的氧化偶联（1 → 6 转化）之外，OvoA 还可以催化 hercynine（2）和半胱氨酸之间的直接氧化偶联（2 → 4 转化），这可以将 ergothioneine 生物合成途径缩短两步。
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