Published February 28, 2022
| Version v1
Journal article
Restricted
Agrocinopine C, a Ti-plasmid-coded enzyme-product, is a 2-O, 6-O linked phosphodiester of D-Glucose and sucrose
Description
Asenstorfer, Robert E., Ryder, Maarten H., Jones, Graham P. (2022): Agrocinopine C, a Ti-plasmid-coded enzyme-product, is a 2-O, 6-O linked phosphodiester of D-Glucose and sucrose. Phytochemistry (113013) 194: 113013, DOI: 10.1016/j.phytochem.2021.113013, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113013
Files
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:0C01FFF055262D122209FFA09F7BEA6C
References
- Angyal, S.J., 1991. The composition of reducing sugars in solution. Adv. Carbohydr. Chem. Biochem. 49, 19-35.
- Angyal, S.J., Pickles, V.A., 1972. Equilibria between pyranoses and furanoses. II. Aldoses. Aust. J. Chem. 25, 1695-1710.
- Avela, E., Aspelund, S., Holmbom, B., Melander, B., Jalonen, H., Peltonen, C., 1977. Selective substitution of sucrose hydroxyl groups via chelates. In: Sucrochemistry, L. Hickson (Ed.), Washington D.C., vol. 41. A.C.S. Symposium Series, USA, pp. 62-79.
- Bartlett, G.R., 1959. Phosphorus assay in column chromatography. J. Biol. Chem. 234, 466-468.
- ChemBioDraw, 2014. Version Ultra 14.0.0.117. PerkinElmer Inc., Waltham MA, USA.
- Chopra, S., Palencia, A., Virus, C., Tripathy, A., Temple, B.R., Velazquez-Campoy, A., Cusack, S., Reader, J.S., 2013. Plant tumour biocontrol agent employs a tRNAdependent mechanism to inhibit leucyl-tRNA synthetase. Nat. Commun. 4, 1417. https://doi.org/10.1038/ncomms2421.
- Clare, B.G., 1995. Agrocins. In: Vining, Leo C., Stuttard, Colin (Eds.), Genetics and Biochemistry of Antibiotic Production. Butterworth-Heinemann Publishers, Oxford, UK, pp. 619-632.
- DePaoli-Roach, A.A., Contreras, C.J., Segvich, D.M., Heiss, C., Ishihara, M., Azadi, P., Roach, P.J., 2015. Glycogen phosphomonoester distribution in mouse models of the progressive myoclonic epilepsy, Lafora disease. J. Biol. Chem. 290, 841-850.
- Dessaux, Y., Petit, A., Farrand, S.K., Murphy, P.J., 1998. Opines and opine-like molecules involved in plant-Rhizobiaceae interactions. In: Spaink, H.P., Kondorosi, A., Hooykaas, P.J.J. (Eds.), The Rhizobiaceae. Kluwer Academic Publishers, Dordrecht, pp. 173-197.
- Dubois, M., Gilles, K., Hamilton, J.K., Rebers, P.A., Smith, F., 1951. A colorimetric method for determination of sugars. Nature 168, 167.
- El Sahili, A., Li, S.-Z., Lang, J., Virus, C., Planamente, S., Ahmar, M., Guimaraes, B.G., Aumont-Nicaise, M., Vigouroux, A., Soulere, L., Reader, J., Queneau, Y., Faure, D., Morera, S., 2015. A pyranose 2-phosphate motif is responsible for both antibiotic import and quorum sensing regulation in Agrobacterium tumefaciens. PLoS Pathog.1-24. https://doi.org/10.1371/journal.ppat.1005071.
- Ellis, J.G., Murphy, P.J., 1981. Four new opines from crown gall tumours - their detection and properties. Mol. Gen. Genet. 181, 36-43.
- Franzkowiak, M., Thiem, J., 1987. Synthesen von Agrocinopin A und B. Liebigs Ann. Chem. 1987, 1065-1071.
- Guyon, P., Chilton, M.D., Petit, A., Temp´e, J., 1980. Agropine in null-type crown gall tumors: evidence for the generality of the opine concept. Proc. Natl. Acad. Sci. U.S.A. 77, 2693-2697.
- Harrap, F.E.G., 1960. The detection of phosphate esters on paper chromatograms. Analyst 85, 452.
- Hayward, L.D., Angyal, S.J., 1977. Symmetry rule for the circular dichroism of reducing sugars, and the proportion of carbonyl forms in aqueous solutions thereof. Carbohydr. Res. 53, 13-20.
- Hough, L., Jones, J.K.N., Wadman, W.H., 1950. Quantitative analysis of mixtures of sugars by the method of partition chromatography; Part V Improved methods for the separation and detection of the sugars and their methylated derivatives on the paper chromatogram. J. Chem. Soc. 1950, 1702-1703.
- Kaufmann, M., Mugge, C., Kroh, L.W., 2018. NMR analyses of complex d-glucose anomerization. Food Chem. 265, 222-226.
- Kerr, A., 2016. Biological control of crown gall. Australas. Plant Pathol. 45, 15-18.
- Kim, H., Farrand, S.K., 1997. Characterization of the acc operon from the nopaline-type Ti plasmid pTiC58, which encodes utilization of agrocinopines A and B and susceptibility to agrocin 84. J. Bacteriol. 179, 7559-7572.
- Kim, H.S., Yi, H., Myung, J., Piper, K.R., Farrand, S.K., 2008. Opine-based Agrobacterium competitiveness: dual expression control of the agrocinopine catabolism (acc) operon by agrocinopines and phosphate levels. J. Bacteriol. 190, 3700-3711. https://doi.org/10.1128/JB.00067-08.
- Kyndt, T., Quispe, D., Zhai, H., Jarret, R., Ghislain, M., Liu, Q., Gheysen, G., Kreuze, J.F., 2015. The genome of cultivated sweet potato contains Agrobacterium T-DNAs with expressed genes: an example of a naturally transgenic food crop. Proc. Natl. Acad. Sci. U. S. A 112, 5844-5849.
- Li, S.-Z., Vigouroux, A., Ahmar, M., El Sahili, A., Soul`ere, L., Sago, L., Cornu, D., Mor´era, S., Queneau, Y., 2019. Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum. Org. Biomol. Chem. 17, 1090-1096.
- 31 Lim, S., Seib, P.A., 1993. Location of phosphate esters in wheat starch phosphate by Pnuclear magnetic resonance spectroscopy. Cereal Chem. 70, 145-215.
- Lindberg, M., Norberg, T., 1988. Synthesis of sucrose 4'-(L-arabinose-2-yl phosphate) (Agrocinopine A) using an arabinose 2-H-phosphonate intermediate. J. Carbohydr. Chem. 7, 749-755.
- Lindberg, M., Norberg, T., Oscarson, S., 1992. Synthesis of sucros-6-yl D-glucos-2-yl phosphate via the hydrogenphosphonate approach. J. Carbohydr. Chem. 11, 243-253.
- Lindberg, M., Oscarson, S., 1993. Synthesis of D-glucos-2-yl sucros-2-yl phosphate (agrocinopin C) and bis (D-glucos-2-yl) phosphate (agrocinopin D). J. Carbohydr. Chem. 12, 1139-1147.
- Los, J.M., Simpson, L.B., Wiesner, K., 1956. The kinetics of mutarotation of D-glucose with consideration of an intermediate free-aldehyde form. J. Am. Chem. Soc. 78, 1564-1568.
- Matveeva, T., Otten, L., 2021. Opine biosynthesis in naturally transgenic plants: genes and products. Phytochemistry (Oxf.) 189. https://doi.org/10.1016/j. phytochem.2021.112813.
- Messens, E., Lenaerts, A., Hedges, R.W., Van Montagu, M., 1985. Agrocinopine A, a phosphorylated opine is secreted from crown gall cells. EMBO J. 4, 571-577.
- Messens, E., Lenaerts, A., Van Montagu, M., De Bruyn, A., Jans, A.W.H., Van Binst, G., 1986. 1 H and 31 P NMR spectroscopy of agrocinopine. J. Carbohydr. Chem. 5, 683-699.
- MestReNova, 2014. MnovaNMRPrediction Software (Version 10.0.0-14381). Mestrelab Research S.L, Santiago de Compostela, Spain.
- Murphy, P.J., Tate, M.E., Kerr, A., 1981. Substituents at N6 and C-5' control selective uptake and toxicity of the adenine-nucleotide bacteriocin, agrocin 84, in agrobacteria. Eur. J. Biochem. 115, 539-543.
- Oger, P., Reich, C., Olsen, G.J., Farrand, S.K., 2001. Complete nucleotide sequence and analysis of pTiBo542: what genomics tells us about structure and evolution of plasmids in the family Rhizobiaceae. Plasmid 45, 169-170.
- O' Connor, J.V., Nunez, H.A., Barker, R., 1979. α- and β- Glucopyranosyl phosphates and 1,2-phosphates. Assignments of conformation in solution by 13 C and 1 H NMR. Biochemistry 18, 500-507.
- Pang, L., Weeks, S.D., Van Aerschot, A., 2021. Aminoacyl-tRNA synthetases as valuable targets for antimicrobial drug discovery. Int. J. Mol. Sci. 22, 1750. https://doi.org/ 10.3390/ijms22041750.
- Ryder, M.H., 1984. Opines in Crown Gall and Hairy Root Diseases. PhD Thesis, University of Adelaide. http://hdl.handle.net/2440/19557.
- Ryder, M.H., Tate, M.E., Jones, G.P., 1984. Agrocinopine A, a tumor-inducing plasmid-coded enzyme product, is a phosphodiester of sucrose and L-arabinose. J. Biol. Chem. 259, 9704-9710.
- Sarfati, R.S., Mondange, M., Szab´o, L., 1977. Phosphorylated sugars. Part 21. Synthesis of 3-deoxy-D-manno-and 3-deoxy-D-gluco-oct-2-ulosonic acid 5-(dihydrogen phosphates). J. Chem. Soc. Perkin Trans. I, 2074-2077.
- Savage, A.E., 1983. The Isolation and Structural Elucidation of Agrocinopine C. B. Ag. Sci. Honours Thesis. The University of Adelaide. http://hdl.handle.net/2440/98296. Sciaky, D., Montoya, A.L., Chilton, M.D., 1978. Fingerprints of Agrobacterium Ti plasmids. Plasmid 1, 238-253.
- Stonier, T., 1960. Agrobacterium tumefaciens Conn. II. Production of an antibiotic substance. J. Bacteriol. 79, 889-898.
- Swenson, C.A., Barker, R., 1971. Proportion of keto and aldehydo forms in solutions of sugars and sugar phosphates. Biochemistry 10, 3151-3154.
- Tate, M.E., 1981. Determination of ionization constants by paper electrophoresis. Biochem. J. 195, 419-426.
- Tate, M.E., Murphy, P.J., Roberts, W.P., Kerr, A., 1979. Adenine N 6 -substituent of agrocin 84 determines its bacteriocin-like specificity. Nature 280, 697-699.
- Travin, D.Y., Severinov, K., Dubiley, S., 2021. Natural Trojan horse inhibitors of aminoacyl-tRNA synthetases. RSC Chem. Biol. https://doi.org/10.1039/ d0cb00208a.
- Trevelyan, W.E., Procter, D.P., Harrison, J.S., 1950. Detection of sugars on paper chromatograms. Nature 166, 444-445.
- Wetzel, M.E., Olsen, G.J., Chakravartty, V., Farrand, S.K., 2015. The repABC plasmids with quorum-regulated transfer systems in members of the Rhizobiales divide into two structurally and separately evolving groups. Genome Biol. Evol. 7, 3337-3357. https://doi.org/10.1093/gbe/evv227.
- Williams, C., Allerhand, A., 1977. Detection of β- D-glucofuranose in aqueous solutions of D-glucose. Application of carbon-13 Fourier-transform n.m.r. spectroscopy. Carbohydr. Res. 56, 173-179.
- Wishart, D.S., Knox, C., Guo, A.C., Eisner, R., Young, N., Gautam, B., Hau, D.D., Psychogios, N., Dong, E., Bouatra, S., Mandal, R., Sinelnikov, I., Xia, J., Jia, L., Cruz, J.A., Lim, E., Sobsey, C.A., Shrivastava, S., Huang, P., Liu, P., Fang, L., Peng, J., Fradette, R., Cheng, D., Tzur, D., Clements, M., Lewis, A., De Souza, A., Zuniga, A., Dawe, M., Xiong, Y., Clive, D., Greiner, R., Nazyrova, A., Shaykhutdinov, R., Li, L., Vogel, H.J., Forsythe, I., 2009. HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 37 (Database issue), D603-D610. https://doi.org/10.1093/nar/ gkn810. Epub 2008 Oct 25. PMID: 18953024; PMCID: PMC2686599.
- Wurster, B., Hess, B., 1974. Anomeric specificity of enzymes of D-glucose metabolism. FEBS Lett. 40, s112-s118.
- Zhang, Q., Li, S.-Z., Ahmar, M., Soul`ere, L., Queneau, Y., 2020. Esters of glucose-2- phosphate: occurrence and chemistry. Molecules 25, 2829. https://doi.org/10.3390/ molecules25122829.