Ruckerbactin Produced by Yersinia ruckeri YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by Vibrio campbellii DS40M4
Ruckerbactin Produced by Yersinia ruckeri YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by Vibrio campbellii DS40M4
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由鲁克氏耶尔森菌 YRB 产生的 Ruckerbactin 是由坎贝氏弧菌 DS40M4 产生的铁载体 Trivanchrobactin 的非对映异构体
DOI：
10.1021/acs.jnatprod.1c01047
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发表时间：
2021
影响因子：
5.1
通讯作者：
Butler, Alison
中科院分区：
文献类型：
--
作者：
Thomsen, Emil;Reitz, Zachary L.;Stow, Parker R.;Dulaney, Kalana;Butler, Alison
革兰氏阴性菌鲁氏耶尔森氏菌是鲑鱼肠道红口病的病原体。 Y 的基因组。 ruckeriYRB 包含一个生物合成基因簇，编码儿茶酚铁载体的生物合成，这些铁载体与已知的 vanchrobactin 类铁载体 (DHBDArgLSer)(1–3) 呈非对映异构体。 Ruckerbactin (1)，由 Y 生产。 ruckeriYRB，被发现是由l-精氨酸和2,3-二羟基苯甲酸组成的线性三-l-丝氨酸酯，(DHBLArgLSer)3。双儿茶酚 (DHBLArgLSer)2(2) 和单儿茶酚 DHBLArgLSer (3) 化合物也被分离和表征。未检测到 Ruckerbactin 的大环内酯。 Ruckerbactin 中 LArg 的存在使其成为 trivanchrobactin 与 DArg 的非对映异构体。 Fe(III)-ruckerbactin 和 Fe(III)-trivanchrobactin 的电子圆二色光谱揭示了 Fe(III) 位点上相反的对映体构型。 Fe(III)-ruckerbactin 采用 Δ 构型，Fe(III)-trivanchrobactin 采用 Λ 构型。 ruckeriYRB 还被发现能产生抗菌剂全霉素 (4)。
The Gram-negative bacteriumYersinia ruckeriis the causative agent for enteric red mouth disease in salmonids. The genome ofY. ruckeriYRB contains a biosynthetic gene cluster encoding the biosynthesis of catechol siderophores that are diastereomeric with the known vanchrobactin class of siderophores, (DHBDArgLSer)(1–3). Ruckerbactin (1), produced byY. ruckeriYRB, was found to be the linear tris-l-serine ester composed ofl-arginine and 2,3-dihydroxybenzoic acid, (DHBLArgLSer)3. The biscatechol, (DHBLArgLSer)2(2), and monocatechol, DHBLArgLSer (3), compounds were also isolated and characterized. The macrolactone of ruckerbactin was not detected. The presence ofLArg in ruckerbactin makes it the diastereomer of trivanchrobactin withDArg. The electronic circular dichroism spectra of Fe(III)–ruckerbactin and Fe(III)–trivanchrobactin reveal the opposite enantiomeric configurations at the Fe(III) sites. Fe(III)–ruckerbactin adopts the Δ configuration, and Fe(III)–trivanchrobactin adopts the Λ configuration.Y. ruckeriYRB was also found to produce the antimicrobial agent holomycin (4).