Hydantocidin: A new compound with herbicidal activity from Streptomyces hygroscopicus.

Nakajima, Mutsuo; Itoi, Kazuko; Takamatsu, Yasuyuki; Kinoshita, Takeshi; Okazaki, Takao; Kawakubo, Katsuhiko; Shindo, Masahiro; Honma, Toyokuni; Tohjigamori, Manabu; Haneishi, Tatsuo

doi:10.7164/antibiotics.44.293

Cited by 221 publications

(93 citation statements)

References 7 publications

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“…Hydantocidin, the furanose analogue of the glucopyranose spirohydantoin, was first isolated from Streptomyces hygroscopicus and shown to have potent herbicide activity against perennial plants (Nakajima et al, 1991). The enzyme adenylosuccinate synthetase, an enzyme essential for de novo synthesis of AMP, has been identified as the herbicide target site (Fonne-Pfister et al, 1996).…”

Section: Gregoriou Et Almentioning

confidence: 99%

The structure of a glycogen phosphorylase glucopyranose spirohydantoin complex at 1.8 Å resolution and 100 K: The role of the water structure and its contribution to binding

et al. 1998

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A glucopyranose spirohydantoin (a pyranose analogue of the potent herbicide, hydantocidin) has been identified as the highest affinity glucose analogue inhibitor of glycogen phosphorylase b (GPb). In order to elucidate the structural features that contribute to the binding, the structures of GPb in the native T state conformation and in complex with glucopyranose spirohydantoin have been determined at 100 K to 2.0 A and 1.8 A resolution, respectively, and refined to crystallographic R values of 0.197 (Rfme 0.248) and 0.1 82 (Rfree 0.229), respectively. The low temperature structure of GPb is almost identical to that of the previously determined room temperature structure, apart from a decrease in overall atomic temperature factors ( ( B ) room temperature GPb = 34.9 A2; ( B ) 1 0 0 K GPb = 23.4 A*). The glucopyranose spirohydantoin inhibitor (K, = 3.0 p M ) binds at the catalytic site and induces small changes in two key regions of the protein: the 280s loop (residues 28 1-286) that results in a decrease in mobility of this region, and the 380s loop (residues 377-385) that undergoes more significant shifts in order to optimize contact to the ligand. The hydantoin group, that is responsible for increasing the affinity of the glucose compound by a factor of IO3, makes only one hydrogen bond to the protein, from one of its NH groups to the main chain oxygen of His377. The other polar groups of the hydantoin group form hydrogen bonds to five water molecules. These waters are involved in extensive networks of hydrogen bonds and appear to be an integral part of the protein structure. Analysis of the water structure at the catalytic site of the native enzyme, shows that five waters are displaced by ligand binding and that there is a significant decrease in mobility of the remaining waters on formation of the GPb-hydantoin complex. The ability of the inhibitor to exploit existing waters, to displace waters and to recruit new waters appears to be important for the high affinity of the inhibitor.Keywords: anti-hyperglycaemic agent; glucopyranose spirohydantoin; glycogen phosphorylase; hydantocidin; inhibitor binding; water structure Glycogen phosphorylase (GP) catalyzes the first step in the phosphorolysis of glycogen to yield glucose-1-phosphate which, in muscle, is utilized via glycolysis to provide energy for muscle contraction and, in the liver, is converted to glucose to supply

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Section: Gregoriou Et Almentioning

confidence: 99%

The structure of a glycogen phosphorylase glucopyranose spirohydantoin complex at 1.8 Å resolution and 100 K: The role of the water structure and its contribution to binding

et al. 1998

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“…Hydantocidin (Figure 3) produced by S. hygroscopicus SANK 13584 is a unique sugar-spiro-hydantoin with potent herbicidal activity (82,93). Chinese cabbage seeds in small test tubes were used for herbicidal assays.…”

Section: New Herbicidal Compounds With Promising Activitymentioning

confidence: 99%

Agroactive Compounds of Microbial Origin

Tanaka¹

1993

Annual Review of Microbiology

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“…1 Particularly, there are different timidine analogs, obtained by a ring contraction strategy, with a five-membered heterocycle, namely methylhydantoin. For example, showdomicin is a broad-spectrum antibiotic isolated from Streptomyces showdoensis.…”

Section: Introductionmentioning

confidence: 99%

Reactivity Study of Methylcyclobutylketones and Cyclobutanones in the Obtention of Analogs of Hydantoinic Nucleosides

Kuran

Moglioni²

2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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Hydantocidin: A new compound with herbicidal activity from Streptomyces hygroscopicus.

Cited by 221 publications

References 7 publications

The structure of a glycogen phosphorylase glucopyranose spirohydantoin complex at 1.8 Å resolution and 100 K: The role of the water structure and its contribution to binding

The structure of a glycogen phosphorylase glucopyranose spirohydantoin complex at 1.8 Å resolution and 100 K: The role of the water structure and its contribution to binding

Agroactive Compounds of Microbial Origin

Reactivity Study of Methylcyclobutylketones and Cyclobutanones in the Obtention of Analogs of Hydantoinic Nucleosides

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