2-[[2-[2-[2-[[4-[(3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)amino]-4-carboxybutanoyl]-methylamino]prop-2-enoylamino]propanoylamino]-4-(4-hydroxyphenyl)butanoyl]amino]-4-[[1-carboxy-4-(diaminomethylideneamino)butyl]amino]-3-methyl-4-oxobutanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 2-[[2-[2-[2-[[4-[(3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)amino]-4-carboxybutanoyl]-methylamino]prop-2-enoylamino]propanoylamino]-4-(4-hydroxyphenyl)butanoyl]amino]-4-[[1-carboxy-4-(diaminomethylideneamino)butyl]amino]-3-methyl-4-oxobutanoic acid
• 英文别名: 2-[[2-[2-[2-[[4-[(3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)amino]-4-carboxybutanoyl]-methylamino]prop-2-enoylamino]propanoylamino]-4-(4-hydroxyphenyl)butanoyl]amino]-4-[[1-carboxy-4-(diaminomethylideneamino)butyl]amino]-3-methyl-4-oxobutanoic acid
• 化学式: C₅₃H₇₆N₁₀O₁₄
• 分子量: 1077.25
• InChiKey: WTVAONJAVUUYCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  77
• 可旋转键数：
  33
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  398
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  microsystin-YR 在 盐酸 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 生成 2-[[2-[2-[2-[[4-[(3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)amino]-4-carboxybutanoyl]-methylamino]prop-2-enoylamino]propanoylamino]-4-(4-hydroxyphenyl)butanoyl]amino]-4-[[1-carboxy-4-(diaminomethylideneamino)butyl]amino]-3-methyl-4-oxobutanoic acid 、 2-[(3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)amino]-5-[[3-(1-carboxyethylamino)-3-oxoprop-1-en-2-yl]-methylamino]-5-oxopentanoic acid 、 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid 、 amino-4-(4-hydroxyphenyl)butanamide
  参考文献：
  名称：

  Pathway for Biodegrading Microcystin-YR by Sphingopyxis sp. USTB-05

  摘要：

  水域中有害的蓝藻水华已成为一个全球性的环境问题，这主要是由于各种微藻毒素的产生和释放，其中微囊藻毒素（MCs）分布广泛。在这里，我们重点研究了微囊藻毒素的一种典型形式，称为微囊藻毒素-YR (MC-YR)。结果发现，初始14.8 mg/L的MC-YR可以在10小时内被Sphingopyxis sp.的粗酶（CEs）完全消除。 USTB-05，我们在之前的研究中分离和鉴定的一种有前途的细菌菌株。在MC-YR随时间的酶促生物降解过程中，在HPLC图谱上分别在238 nm和230 nm波长处观察到两个中间产物和两个最终产物的峰。基于LC-MS/MS对MC-YR及其四种产物的m/z比的分析，我们认为至少有四种酶参与了Sphingopyxis sp.对MC-YR的生物降解。 USTB-05。第一种酶微胱氨酸酶将环状 MC-YR 转化为线性 MC-YR，作为第一种产品。然后发现第二酶丝氨酸蛋白酶切割线性化MC-YR的丙氨酸(Ala)和酪氨酸(Tyr)之间的目标肽键，产生四肽和三肽作为第二产物，分别是Adda-Glu-Mdha-Ala和分别是 Tyr-Masp-Arg。接下来，第三酶肽酶将Adda-Glu-Mdha-Ala四肽转化为Adda。第四种酶将Tyr-Masp-Arg的三肽裂解产生Tyr和二肽(Masp-Arg)，这从未被报道过。这些发现将帮助我们更好地了解鞘氨醇杆菌 (Sphingopyxis sp.) 对 MC-YR 的生物降解途径。 USTB-05。

  DOI：

  10.1371/journal.pone.0124425

文献信息

• Pathway for Biodegrading Microcystin-YR by Sphingopyxis sp. USTB-05
  作者：Huimin Xu、Huasheng Wang、Qianqian Xu、Le Lv、Chunhua Yin、Xiaolu Liu、Hongwu Du、Hai Yan

  DOI：10.1371/journal.pone.0124425

  日期：——

  Harmful cyanobacterial blooms in waters have become a global environmental problem, this mainly due to the production and release of various microalgal toxins, in which microcystins (MCs) are distributed widely. Here, we focused on the study of a typical form of microcystins called microcystin-YR (MC-YR). It was found that initial 14.8 mg/L of MC-YR could be completely eliminated within 10 hr by the crude enzymes (CEs) of Sphingopyxis sp. USTB-05, a promising bacterial strain we isolated and identified in our previous study. During the enzymatic biodegradation of MC-YR with time course, the peaks of two intermediate and two final products were observed on the profiles of HPLC at the wavelengths of 238 nm and 230 nm, respectively. Based on the analysis of m/z ratios of MC-YR and its four products by LC-MS/MS, we suggested that at least four enzymes were involved in the biodegradation of MC-YR by Sphingopyxis sp. USTB-05. The first enzyme microcystinase converted cyclic MC-YR to linear MC-YR as the first product. Then the second enzyme serine protease was found to cleave the target peptide bond between alanine (Ala) and tyrosine (Tyr) of linearized MC-YR, producing a tetrapeptide and a tripeptide as second products, which were Adda-Glu-Mdha-Ala and Tyr-Masp-Arg, respectively. Next, the third enzyme peptidase converted the tetrapeptide of Adda-Glu-Mdha-Ala to Adda. And the fourth enzyme cleaved the tripeptide of Tyr-Masp-Arg to produce Tyr and dipeptide (Masp-Arg), which has never been reported. These findings will help us better understand the biodegradation pathway of MC-YR by Sphingopyxis sp. USTB-05.

  水域中有害的蓝藻水华已成为一个全球性的环境问题，这主要是由于各种微藻毒素的产生和释放，其中微囊藻毒素（MCs）分布广泛。在这里，我们重点研究了微囊藻毒素的一种典型形式，称为微囊藻毒素-YR (MC-YR)。结果发现，初始14.8 mg/L的MC-YR可以在10小时内被Sphingopyxis sp.的粗酶（CEs）完全消除。 USTB-05，我们在之前的研究中分离和鉴定的一种有前途的细菌菌株。在MC-YR随时间的酶促生物降解过程中，在HPLC图谱上分别在238 nm和230 nm波长处观察到两个中间产物和两个最终产物的峰。基于LC-MS/MS对MC-YR及其四种产物的m/z比的分析，我们认为至少有四种酶参与了Sphingopyxis sp.对MC-YR的生物降解。 USTB-05。第一种酶微胱氨酸酶将环状 MC-YR 转化为线性 MC-YR，作为第一种产品。然后发现第二酶丝氨酸蛋白酶切割线性化MC-YR的丙氨酸(Ala)和酪氨酸(Tyr)之间的目标肽键，产生四肽和三肽作为第二产物，分别是Adda-Glu-Mdha-Ala和分别是 Tyr-Masp-Arg。接下来，第三酶肽酶将Adda-Glu-Mdha-Ala四肽转化为Adda。第四种酶将Tyr-Masp-Arg的三肽裂解产生Tyr和二肽(Masp-Arg)，这从未被报道过。这些发现将帮助我们更好地了解鞘氨醇杆菌 (Sphingopyxis sp.) 对 MC-YR 的生物降解途径。 USTB-05。