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Chemical Compound Review

mannopine     (2S)-4-aminocarbonyl-2- [[(2R,3R,4R,5R)-2,3...

Synonyms: AC1L3TJG, AC1Q5QTL, AR-1I6821, C16692, 87084-52-4
 
 
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Disease relevance of mannopine

 

High impact information on mannopine

  • Agrobacterium rhizogenes pRi8196 T-DNA: mapping and DNA sequence of functions involved in mannopine synthesis and hairy root differentiation [6].
  • This gene is located in an operon coding for a mannopine transport system and is expressed as part of the mannityl opine regulon [7].
  • Tissue-specific and wound-inducible pattern of expression of the mannopine synthase promoter is determined by the interaction between positive and negative cis-regulatory elements [8].
  • In transgenic tobacco plants the regulatory region of the Agrobacterium genes involved in mannopine synthesis (pmas) directs expression in vascular tissues and is induced upon wounding [8].
  • Two cosmid clones of pAtC58 allowed UIA5, a plasmid-free derivative of C58, harboring pSa-C that expresses MocC (mannopine [MOP] oxidoreductase that oxidizes MOP to DFG), to grow by using MOP as the sole carbon source [9].
 

Chemical compound and disease context of mannopine

 

Biological context of mannopine

  • This paper presents the map and DNA sequence analysis of pRi8196 transferred DNA (T-DNA) genes encoding root-inducing and mannopine synthesis functions [6].
  • A Ti plasmid-encoded enzyme required for degradation of mannopine is functionally homologous to the T-region-encoded enzyme required for synthesis of this opine in crown gall tumors [12].
  • Forty-five individually transformed clonal tobacco callus lines were simultaneously assayed for both chloramphenicol acetyltransferase (CAT) and beta-glucuronidase (GUS) activity resulting from expression of introduced reporter genes driven by the adjacent and divergent mannopine (mas) promoters [13].
  • A clone conferring the ability to utilize mannopine on a recipient pseudomonad was selected from a genomic library from both the mutant LM136 and its parent strain [14].
  • Effects of sub-cellular compartments on E1 production and its stability were determined in transgenic tobacco plants carrying one of six transgene expression vectors, where the E1 was under the control of Mac promoter, mannopine synthase transcription terminator, and one of the five transit peptides [15].
 

Anatomical context of mannopine

  • Multiple ocs-like elements required for efficient transcription of the mannopine synthase gene of T-DNA in maize protoplasts [16].
  • A gene encoding the cholera toxin B subunit protein (CTB), fused to an endoplasmic reticulum (ER) retention signal (SEKDEL) was inserted adjacent to the bi-directional mannopine synthase P2 promoter in a plant expression vector containing a bacterial luciferase AB fusion gene (luxF) linked to the P1 promoter [17].
 

Associations of mannopine with other chemical compounds

 

Gene context of mannopine

  • The second, mocD dissimilates DFG formed in the pathway for catabolism of mannopine (MOP) a non-Amadori, imine-type member of the mannityl opine family characteristic of certain Ti and Ri plasmids [20].
  • A 479-bp bi-directional promoter controls the expression of two genes (mas1' and mas2') that encode enzymes for the synthesis of the opine mannopine in plant tissues infected with Agrobacterium tumefaciens [21].
  • The reductase activity of this enzyme is precisely the reaction ascribed to its T-region-encoded homolog, Mas1, which is responsible for biosynthesis of mannopine in crown gall tumors [12].
 

Analytical, diagnostic and therapeutic context of mannopine

  • Quantification of gallerimycin mRNA in transgenic tobacco by real-time PCR confirmed transgenic expression under control of the inducible mannopine synthase promoter [22].
  • High-voltage paper electrophoresis (HVPE) analysis demonstrated the production of mannopine in hairy roots and confirmed the successful transfer of Ri T-DNA (root-inducing transferred DNA) of A. rhizogenes into the I. indigotica genome [23].

References

  1. Integration and expression of a rabbit liver cytochrome P-450 gene in transgenic Nicotiana tabacum. Saito, K., Noji, M., Ohmori, S., Imai, Y., Murakoshi, I. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  2. Characteristics of a strong promoter from figwort mosaic virus: comparison with the analogous 35S promoter from cauliflower mosaic virus and the regulated mannopine synthase promoter. Sanger, M., Daubert, S., Goodman, R.M. Plant Mol. Biol. (1990) [Pubmed]
  3. Mannopine and mannopinic acid as substrates for Arthrobacter sp. strain MBA209 and Pseudomonas putida NA513. Nautiyal, C.S., Dion, P., Chilton, W.S. J. Bacteriol. (1991) [Pubmed]
  4. A T-DNA gene required for agropine biosynthesis by transformed plants is functionally and evolutionarily related to a Ti plasmid gene required for catabolism of agropine by Agrobacterium strains. Hong, S.B., Hwang, I., Dessaux, Y., Guyon, P., Kim, K.S., Farrand, S.K. J. Bacteriol. (1997) [Pubmed]
  5. A tobacco homologue of the Ri-plasmid orf13 gene causes cell proliferation in carrot root discs. Fründt, C., Meyer, A.D., Ichikawa, T., Meins, F. Mol. Gen. Genet. (1998) [Pubmed]
  6. Agrobacterium rhizogenes pRi8196 T-DNA: mapping and DNA sequence of functions involved in mannopine synthesis and hairy root differentiation. Hansen, G., Larribe, M., Vaubert, D., Tempé, J., Biermann, B.J., Montoya, A.L., Chilton, M.D., Brevet, J. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  7. Octopine-type Ti plasmids code for a mannopine-inducible dominant-negative allele of traR, the quorum-sensing activator that regulates Ti plasmid conjugal transfer. Oger, P., Kim, K.S., Sackett, R.L., Piper, K.R., Farrand, S.K. Mol. Microbiol. (1998) [Pubmed]
  8. Tissue-specific and wound-inducible pattern of expression of the mannopine synthase promoter is determined by the interaction between positive and negative cis-regulatory elements. Guevara-García, A., Mosqueda-Cano, G., Argüello-Astorga, G., Simpson, J., Herrera-Estrella, L. Plant J. (1993) [Pubmed]
  9. Convergent evolution of Amadori opine catabolic systems in plasmids of Agrobacterium tumefaciens. Baek, C.H., Farrand, S.K., Lee, K.E., Park, D.K., Lee, J.K., Kim, K.S. J. Bacteriol. (2003) [Pubmed]
  10. Intracellular accumulation of mannopine, an opine produced by crown gall tumors, transiently inhibits growth of Agrobacterium tumefaciens. Kim, K.S., Baek, C.H., Lee, J.K., Yang, J.M., Farrand, S.K. Mol. Plant Microbe Interact. (2001) [Pubmed]
  11. Diauxic growth of Agrobacterium tumefaciens 15955 on succinate and mannopine. Nautiyal, C.S., Dion, P., Chilton, W.S. J. Bacteriol. (1992) [Pubmed]
  12. A Ti plasmid-encoded enzyme required for degradation of mannopine is functionally homologous to the T-region-encoded enzyme required for synthesis of this opine in crown gall tumors. Kim, K.S., Chilton, W.S., Farrand, S.K. J. Bacteriol. (1996) [Pubmed]
  13. Transgene expression variability (position effect) of CAT and GUS reporter genes driven by linked divergent T-DNA promoters. Peach, C., Velten, J. Plant Mol. Biol. (1991) [Pubmed]
  14. Spontaneous mutation conferring the ability to catabolize mannopine in Agrobacterium tumefaciens. LaPointe, G., Nautiyal, C.S., Chilton, W.S., Farrand, S.K., Dion, P. J. Bacteriol. (1992) [Pubmed]
  15. Optimization of Acidothermus cellulolyticus endoglucanase (E1) production in transgenic tobacco plants by transcriptional, post-transcription and post-translational modification. Dai, Z., Hooker, B.S., Quesenberry, R.D., Thomas, S.R. Transgenic Res. (2005) [Pubmed]
  16. Multiple ocs-like elements required for efficient transcription of the mannopine synthase gene of T-DNA in maize protoplasts. Fox, P.C., Vasil, V., Vasil, I.K., Gurley, W.B. Plant Mol. Biol. (1992) [Pubmed]
  17. Expression of cholera toxin B subunit oligomers in transgenic potato plants. Arakawa, T., Chong, D.K., Merritt, J.L., Langridge, W.H. Transgenic Res. (1997) [Pubmed]
  18. Effect of crop rotation and soil cover on alteration of the soil microflora generated by the culture of transgenic plants producing opines. Oger, P., Mansouri, H., Dessaux, Y. Mol. Ecol. (2000) [Pubmed]
  19. Genetic transformation of Pueraria phaseoloides with Agrobacterium rhizogenes and puerarin production in hairy roots. Shi, H.P., Kintzios, S. Plant Cell Rep. (2003) [Pubmed]
  20. Genes for utilization of deoxyfructosyl glutamine (DFG), an amadori compound, are widely dispersed in the family Rhizobiaceae. Baek, C.H., Farrand, S.K., Park, D.K., Lee, K.E., Hwang, W., Kim, K.S. FEMS Microbiol. Ecol. (2005) [Pubmed]
  21. The mannopine synthase promoter contains vectorial cis-regulatory elements that act as enhancers and silencers. Guevara-García, A., López-Bucio, J., Herrera-Estrella, L. Mol. Gen. Genet. (1999) [Pubmed]
  22. Transgenic expression of gallerimycin, a novel antifungal insect defensin from the greater wax moth Galleria mellonella, confers resistance to pathogenic fungi in tobacco. Langen, G., Imani, J., Altincicek, B., Kieseritzky, G., Kogel, K.H., Vilcinskas, A. Biol. Chem. (2006) [Pubmed]
  23. Production and analysis of organic acids in hairy-root cultures of Isatis indigotica Fort. (indigo woad). Xu, T., Zhang, L., Sun, X., Zhang, H., Tang, K. Biotechnol. Appl. Biochem. (2004) [Pubmed]
 
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