Structural characterization of four prochlorosins: a novel class of lantipeptides produced by planktonic marine cyanobacteria.
Structural characterization of four prochlorosins: a novel class of lantipeptides produced by planktonic marine cyanobacteria.
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DOI：
10.1021/bi300255s
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发表时间：
2012-05-29
期刊：
影响因子：
2.9
通讯作者：
van der Donk WA
中科院分区：
文献类型：
--
作者：
Tang W;van der Donk WA
原绿菌素是由原绿球藻产生的一类次级代谢产物。这些多环肽含有导致硫醚交联的羊毛硫醚和甲基羊毛硫醚残基。在原绿球藻MIT 9313中，一种单一的酶ProcM催化29种线性肽底物的翻译后修饰，以产生高度多样化的环肽文库。为了研究ProcM的催化混杂性，我们选择了四种先前证明由生物体产生的prochlorosins进行详细的结构表征。核磁共振研究允许明确分配的环拓扑结构，表现出高度的拓扑多样性。采用气相色谱-质谱联用技术对7种丙绿素的稀土和甲基稀土残基进行了立体化学分析。所有甲基羊毛硫氨酸都具有（2S，3S，6 R）构型，并且羊毛硫氨酸具有（2S，6 R）构型，而与环化方向、环大小或环拓扑结构无关。这些研究结果表明，大多数，如果不是全部，在prochlorosins环酶促形成的ProcM lanthidine合成酶，而不是由非酶的过程，如前所述。
Prochlorosins make up a class of secondary metabolites produced by strains of Prochlorococcus, single-cell, planktonic marine cyanobacteria. These polycyclic peptides contain lanthionine and methyllanthionine residues that result in thioether cross-links. In Prochlorococcus MIT9313, a single enzyme, ProcM, catalyzes the posttranslational modification of 29 linear peptide substrates to generate a library of highly diverse cyclic peptides. To investigate the catalytic promiscuity of ProcM, we chose four prochlorosins previously demonstrated to be produced by the organism for detailed structural characterization. Nuclear magnetic resonance studies allowed unambiguous assignment of the ring topologies, demonstrating a high degree of topological diversity. The stereochemistry of the lanthionine and methyllanthionine residues was determined by gas chromatography and mass spectrometry for seven prochlorosins. All methyllanthionines had the (2S,3S,6R) configuration, and the lanthionines had the (2S,6R) configuration, irrespective of the direction of cyclization, ring size, or ring topology. These findings indicate that most, if not all, of the rings in prochlorosins are formed enzymatically by ProcM lanthionine synthetase and not by a nonenzymatic process as previously suggested.
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影响因子：
15
作者：
Liu, Wei;Chan, Alice S. H.;Vederas, John C.
通讯作者：
Vederas, John C.
DOI：
10.1073/pnas.0913677107
发表时间：
2010-06-08
影响因子：
11.1
作者：
Li, Bo;Sher, Daniel;van der Donk, Wilfred A.
通讯作者：
van der Donk, Wilfred A.
影响因子：
2.9
作者：
Martin, NI;Sprules, T;Vederas, JC
通讯作者：
Vederas, JC
影响因子：
2.9
作者：
Helfrich, Markus;Entian, Karl-Dieter;Stein, Torsten
通讯作者：
Stein, Torsten
影响因子：
2.7
作者：
DELAGLIO, F;GRZESIEK, S;BAX, A
通讯作者：
BAX, A