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Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B.
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2019-11-19 , DOI: 10.1021/acschembio.9b00620 Antti Mattila 1 , Rose-Marie Andsten 1 , Mikael Jumppanen 2 , Michele Assante 2 , Jouni Jokela 1 , Matti Wahlsten 1 , Kornelia M Mikula 3 , Cihad Sigindere 4 , Daniel H Kwak 4 , Muriel Gugger 5 , Harri Koskela 6 , Kaarina Sivonen 1 , Xinyu Liu 4 , Jari Yli-Kauhaluoma 2 , Hideo Iwaï 3 , David P Fewer 1
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2019-11-19 , DOI: 10.1021/acschembio.9b00620 Antti Mattila 1 , Rose-Marie Andsten 1 , Mikael Jumppanen 2 , Michele Assante 2 , Jouni Jokela 1 , Matti Wahlsten 1 , Kornelia M Mikula 3 , Cihad Sigindere 4 , Daniel H Kwak 4 , Muriel Gugger 5 , Harri Koskela 6 , Kaarina Sivonen 1 , Xinyu Liu 4 , Jari Yli-Kauhaluoma 2 , Hideo Iwaï 3 , David P Fewer 1
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Prenylation is a common step in the biosynthesis of many natural products and plays an important role in increasing their structural diversity and enhancing biological activity. Muscoride A is a linear peptide alkaloid that contain two contiguous oxazoles and unusual prenyl groups that protect the amino- and carboxy-termini. Here we identified the 12.7 kb muscoride (mus) biosynthetic gene clusters from Nostoc spp. PCC 7906 and UHCC 0398. The mus biosynthetic gene clusters encode enzymes for the heterocyclization, oxidation, and prenylation of the MusE precursor protein. The mus biosynthetic gene clusters encode two copies of the cyanobactin prenyltransferase, MusF1 and MusF2. The predicted tetrapeptide substrate of MusF1 and MusF2 was synthesized through a novel tandem cyclization route in only eight steps. Biochemical assays demonstrated that MusF1 acts on the carboxy-terminus while MusF2 acts on the amino-terminus of the tetrapeptide substrate. We show that the MusF2 enzyme catalyzes the reverse or forward prenylation of amino-termini from Nostoc spp. PCC 7906 and UHCC 0398, respectively. This finding expands the regiospecific chemical functionality of cyanobactin prenyltransferases and the chemical diversity of the cyanobactin family of natural products to include bis-prenylated polyoxazole linear peptides.
中文翻译：
双异戊酸酯化生物碱Muscoride A和B的生物合成。
异戊烯基化是许多天然产物生物合成中的一个常见步骤，并且在增加其结构多样性和增强生物活性方面起着重要作用。Muscoride A是一种线性肽生物碱，其中包含两个连续的恶唑和不寻常的异戊二烯基，可保护氨基和羧基末端。在这里，我们从Nostoc spp鉴定了12.7 kb muscoride（mus）生物合成基因簇。PCC 7906和UHCC0398。mus生物合成基因簇编码MusE前体蛋白杂环化，氧化和异戊二烯化的酶。mus生物合成基因簇编码了两个副本的cyanobactin异戊二烯基转移酶MusF1和MusF2。通过新颖的串联环化途径仅八步合成了MusF1和MusF2的预测四肽底物。生化分析表明，MusF1作用于羧基末端，而MusF2作用于四肽底物的氨基末端。我们显示，MusF2酶催化Nostoc spp氨基末端的反向或正向烯丙基化。分别是PCC 7906和UHCC 0398。这一发现扩展了氰基细菌素异戊二烯基转移酶的区域特异性化学功能和天然产物氰基细菌素家族的化学多样性，使其包括双-异戊烯基化的聚恶唑线性肽。
更新日期：2019-11-20
中文翻译：
双异戊酸酯化生物碱Muscoride A和B的生物合成。
异戊烯基化是许多天然产物生物合成中的一个常见步骤，并且在增加其结构多样性和增强生物活性方面起着重要作用。Muscoride A是一种线性肽生物碱，其中包含两个连续的恶唑和不寻常的异戊二烯基，可保护氨基和羧基末端。在这里，我们从Nostoc spp鉴定了12.7 kb muscoride（mus）生物合成基因簇。PCC 7906和UHCC0398。mus生物合成基因簇编码MusE前体蛋白杂环化，氧化和异戊二烯化的酶。mus生物合成基因簇编码了两个副本的cyanobactin异戊二烯基转移酶MusF1和MusF2。通过新颖的串联环化途径仅八步合成了MusF1和MusF2的预测四肽底物。生化分析表明，MusF1作用于羧基末端，而MusF2作用于四肽底物的氨基末端。我们显示，MusF2酶催化Nostoc spp氨基末端的反向或正向烯丙基化。分别是PCC 7906和UHCC 0398。这一发现扩展了氰基细菌素异戊二烯基转移酶的区域特异性化学功能和天然产物氰基细菌素家族的化学多样性，使其包括双-异戊烯基化的聚恶唑线性肽。
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