Synthesis of the Quinoline-Linked Triazolopyrimidine Analogues and Their Interactions with the Recombinant Tobacco Acetolactate Synthase

Namgoong, Sung Keon; Lee, Hyun Jung; Kim, Young Sook; Shin, Jonghoon; Che, Jong-Khn; Jang, Do Young; Kim, Gun Sung; Yoo, Jae Won; Kang, Moon-Kyeong; Kil, Mee-Wha; Choi, Jung‐Do; Chang, Soo-Ik

doi:10.1006/bbrc.1999.0708

Cited by 20 publications

(9 citation statements)

References 22 publications

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“…Previously, AHAS was identified as a target for various classes of herbicides (2)(3)(4)(5)(6). Therefore, the inhibitions of the mutant AHASs by the three classes of herbicides, Londax (sulfonylurea), Cadre (an imidazolinone), and TP (a triazolopyrimidine) were determined.…”

Section: Discussionmentioning

confidence: 99%

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Roles of Three Well-Conserved Arginine Residues in Mediating the Catalytic Activity of Tobacco Acetohydroxy Acid Synthase

Le¹,

Yoon²,

Kim³

et al. 2005

The Journal of Biochemistry

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Acetohydroxy acid synthase (AHAS, EC 2.2.1.6; also known as acetolactate synthase, ALS) catalyzes the first common step in the biosynthesis of valine, leucine, and isoleucine in plants and microorganisms. AHAS is the target of several classes of herbicides. In the present study, the role of three well-conserved arginine residues (R141, R372, and R376) in tobacco AHAS was determined by site-directed mutagenesis. The mutated enzymes, referred to as R141A, R141F, and R376F, were inactive and unable to bind to the cofactor, FAD. The inactive mutants had the same secondary structure as that of the wild type. The mutants R141K, R372F, and R376K exhibited much lower specific activities than the wild type, and moderate resistance to herbicides such as Londax, Cadre, and/or TP. The mutation R141K showed a strong reduction in activation efficiency by ThDP, while the mutations R372K and R376K showed a strong

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Section: Discussionmentioning

confidence: 99%

“…AHAS requires three cofactors for its catalytic activity, thiamine diphosphate (ThDP), flavin adenine dinucleotide (FAD), and divalent metal ion, Mg 2+ or Mn 2+ . AHAS has been demonstrated to be the target of several classes of modern and potent herbicides, including sulfonylureas (2,3), imidazolinones (4), and triazolopyrimidines (5,6).…”

mentioning

confidence: 99%

Roles of Three Well-Conserved Arginine Residues in Mediating the Catalytic Activity of Tobacco Acetohydroxy Acid Synthase

Le¹,

Yoon²,

Kim³

et al. 2005

The Journal of Biochemistry

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“…AHAS has attracted much interest since it was demonstrated to be the target of several classes of modern and potent herbicides, including the sulfonylureas, 2,3 the imidazolinones, 4 and the triazolopyrimidines. 5,6 AHAS activity is found in bacteria, yeast, and plants resulting from one or more isozymes. In bacteria, three AHAS isozymes have been studied extensively in term of their genetic regulation, kinetic properties, feedback regulation, and sensitivity to herbicidal inhibitors.…”

Section: +mentioning

confidence: 99%

Lag Time of the Recombinant Acetohydroxy Acid Synthase from Tobacco

2003

Bulletin of the Korean Chemical Society

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“…1. The herbicides, acting as branched chain amino acid (leucine, isoleucine, and valine) synthesis (acetolactate synthase) inhibitors (Baumgartner et al 1999;Namgoong et al 1999), are taken up by root and shoots, translocated to growth points and result in chlorosis and necrosis of the plant (Baghestani et al 2007). A combination of the two herbicides, at low doses of active ingredient, provides an effective control of a wide spectrum of broadleaved weeds such as Sinapis arvensis L. (wild mustard) and Galium aparine L. (bedstraw) in wheat, barley, and corn (Baghestani et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Dissipation kinetics and residues of triazolopyrimidine herbicides flumetsulam and florasulam in corn ecosystem

Zhong

Wang

2015

Environ Monit Assess

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The dynamic and residues of florasulam and flumetsulam in corn field ecosystem were investigated using quick, easy, cheap, effective, rugged, and safe (QuEChERS) procedure with high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The limits of quantification (LOQs) of the proposed method ranged from 0.005 to 0.01 mg/kg. Mean recoveries and relative standard deviations (RSDs) of the two compounds in all samples at three spiking levels ranged 94-110 % and 2.0-9.2 %, respectively. Florasulam and flumetsulam degradation followed first-order kinetics with half-lives 1.7-2.9 and 3.3-8.7 days in soil and 1.3-1.8 and 0.9-1.7 days in plant, respectively. The residues in all the samples were found to be less than the LOQs at preharvest intervals of 53 and 78 days. The results suggest that the combined use of florasulam and flumetsulam on corn is considered to be safe under the recommended conditions and can be utilized for establishing the maximum residue limit (MRL) of florasulam in corn in China.

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Synthesis of the Quinoline-Linked Triazolopyrimidine Analogues and Their Interactions with the Recombinant Tobacco Acetolactate Synthase

Cited by 20 publications

References 22 publications

Roles of Three Well-Conserved Arginine Residues in Mediating the Catalytic Activity of Tobacco Acetohydroxy Acid Synthase

Roles of Three Well-Conserved Arginine Residues in Mediating the Catalytic Activity of Tobacco Acetohydroxy Acid Synthase

Lag Time of the Recombinant Acetohydroxy Acid Synthase from Tobacco

Dissipation kinetics and residues of triazolopyrimidine herbicides flumetsulam and florasulam in corn ecosystem

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