title: Binding interactions between enantiomeric α-aminophosphonate derivatives and tobacco mosaic virus coat protein.
abstract: Tobacco mosaic virus (TMV) is an important plant virus that can cause considerable crop loss. Our group synthesized a series of enantiomeric α-aminophosphonate derivatives with high anti-TMV activities. The activity of (R)-diphenyl-1-(4-methylbenzothiazole-2-amino)-1-(thiphene-2-yl)-methylphosphonate (Q-R) was found to be superior to that of (S)-diphenyl-1-(4-methyl benzothiazole-2-amino)-1-(thiphene-2-yl)-methylphosphonate (Q-S). However, the mechanism for inhibition of the R-isomer (Q-R) of infection activity is not clear. Thus, we studied the interactions between Q-R and Q-S and TMV by using TMV coat proteins (CP) as a potential target for fluorescence spectroscopy, isothermal titration calorimetry, microscale thermophoresis, and molecular docking. Arg90 was found to play a major role in the interaction of Q-R with TMV CP, as demonstrated by the interaction experiments and the results of molecular modeling. The substitution of arginine with glycine resulted in a mutant that was significantly less sensitive to Q-R. These results indicate that Q-R undermines the structural stability of the TMV R90G virus particle by binding with Arg90, eventually leading to the loss of the virus' ability for infection.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Weiying
authors.initials: W
authors.lastname: Zhang
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Xiangyang
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Guoping
authors.initials: G
authors.lastname: Zhang
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Ding
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Longlu
authors.initials: L
authors.lastname: Ran
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Liangzhi
authors.initials: L
authors.lastname: Luo
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Jian
authors.initials: J
authors.lastname: Wu
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China. Electronic address: songbaoan22@yahoo.com.
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
mesh_terms: D019943:Amino Acid Substitution; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001120:Arginine / Q000737:chemistry*; D036022:Capsid Proteins / Q000737:chemistry* / Q000235:genetics; D015870:Gene Expression; D005998:Glycine / Q000737:chemistry*; D062105:Molecular Docking Simulation; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D011485:Protein Binding; D017433:Protein Structure, Secondary; D011994:Recombinant Proteins / Q000737:chemistry / Q000235:genetics; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014027:Tobacco Mosaic Virus / Q000737:chemistry*
chemical_list: D000998:Antiviral Agents; D036022:Capsid Proteins; D063065:Organophosphonates; D011994:Recombinant Proteins; D001120:Arginine; D005998:Glycine
keywords: Arg90; Enantiomeric α-aminophosphonate derivatives; Interactions; TMV CP