Cyanohydrin phosphonate natural product from Streptomyces regensis.
Cyanohydrin phosphonate natural product from Streptomyces regensis.
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DOI：
10.1021/np400722m
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发表时间：
2014-02-28
影响因子：
5.1
通讯作者：
Metcalf WW
中科院分区：
文献类型：
--
作者：
Cioni JP;Doroghazi JR;Ju KS;Yu X;Evans BS;Lee J;Metcalf WW
regensis链霉菌（Streptomyces regensis）菌株wp -3744在大规模微生物筛选中被鉴定为潜在的磷酸生产者，因为pepM基因编码磷酸烯醇丙酮酸磷酸酯酶。经核磁共振（31P NMR）分析发现，绿茎生长后的废培养基中存在几种未识别的磷酸盐。这些化合物通过广泛的一维和二维核磁共振光谱和质谱分析进行了纯化和结构表征。观察到三种新的膦酸代谢物，它们的结构通过化学合成标准物的比较得到了证实：（2-乙酰氨基乙基）膦酸(1)、（2-乙酰氨基-1-羟乙基）膦酸(3)和一种新的含氰氢膦酸盐（氰基（羟基）甲基）膦酸(4)。负责合成这些分子的基因簇也从S. regensis的草图基因组序列中被鉴定出来，为未来研究导致这种不寻常的天然产物的代谢途径奠定了基础。
Streptomyces regensis strain WC-3744 was identified as a potential phosphonic acid producer in a large-scale screen of microorganisms for the presence of the pepM gene, which encodes the key phosphonate biosynthetic enzyme phosphoenolpyruvate phosphonomutase. 31P NMR revealed the presence of several unidentified phosphonates in spent medium after growth of S. regensis. These compounds were purified and structurally characterized via extensive 1D and 2D NMR spectroscopic and mass spectrometric analyses. Three new phosphonic acid metabolites, whose structures were confirmed by comparison to chemically synthesized standards, were observed: (2-acetamidoethyl)phosphonic acid (1), (2-acetamido-1-hydroxyethyl)phosphonic (3), and a novel cyanohydrin-containing phosphonate, (cyano(hydroxy)methyl)phosphonic acid (4). The gene cluster responsible for synthesis of these molecules was also identified from the draft genome sequence of S. regensis, laying the groundwork for future investigations into the metabolic pathway leading to this unusual natural product.
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DOI：
10.1016/s0006-291x(88)81205-1
发表时间：
1988-05-31
影响因子：
3.1
作者：
BARRY, RJ;BOWMAN, E;DUNAWAYMARIANO, D
通讯作者：
DUNAWAYMARIANO, D
DOI：
10.1111/j.1432-1033.1983.tb07436.x
发表时间：
1983-01-01
期刊：
EUROPEAN JOURNAL OF BIOCHEMISTRY
影响因子：
--
作者：
DUMORA, C;LACOSTE, AM;CASSAIGNE, A
通讯作者：
CASSAIGNE, A
影响因子：
--
作者：
Circello BT;Eliot AC;Lee JH;van der Donk WA;Metcalf WW
通讯作者：
Metcalf WW
DOI：
10.1002/jlac.1989198901101
发表时间：
1989-06-01
期刊：
LIEBIGS ANNALEN DER CHEMIE
影响因子：
--
作者：
HAMMERSCHMIDT, F;VOLLENKLE, H
通讯作者：
VOLLENKLE, H
影响因子：
2.9
作者：
Chen, CCH;Zhang, H;Herzberg, O
通讯作者：
Herzberg, O