Octopine (BioDeep_00000003161)

 

Secondary id: BioDeep_00001869783

natural product


代谢物信息卡片


N2-(D-1-Carboxyethyl)-L-arginine

化学式: C9H18N4O4 (246.1327988)
中文名称: 章鱼碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.1%

分子结构信息

SMILES: CC(C(=O)O)NC(CCCN=C(N)N)C(=O)O
InChI: InChI=1S/C9H18N4O4/c1-5(7(14)15)13-6(8(16)17)3-2-4-12-9(10)11/h5-6,13H,2-4H2,1H3,(H,14,15)(H,16,17)(H4,10,11,12)

描述信息

The (1R)-1-carboxyethyl derivative of L-arginine. It is a metabolite released by plant tumours.
KEIO_ID O009; [MS2] KO009138
KEIO_ID O009

同义名列表

6 个代谢物同义名

Octopine; D-(+)-Octopine; D-Octopine; N2-(D-1-Carboxyethyl)-L-arginine; N2-(1-Carboxyethyl)-L-arginine; (+)-Octopine



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Rosa Padilla, Vincent Gaillard, Thao Nhi Le, Floriant Bellvert, David Chapulliot, Xavier Nesme, Yves Dessaux, Ludovic Vial, Céline Lavire, Isabelle Kerzaon. Development and validation of a UHPLC-ESI-QTOF mass spectrometry method to analyze opines, plant biomarkers of crown gall or hairy root diseases. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Jan; 1162(?):122458. doi: 10.1016/j.jchromb.2020.122458. [PMID: 33383499]
  • K Habbadi, Q Duplay, D Chapulliot, I Kerzaon, R Benkirane, A Benbouazza, F Wisniewski-Dyé, C Lavire, E H Achbani, L Vial. Characterization and phylogenetic diversity of Allorhizobium vitis isolated from grapevine in Morocco. Journal of applied microbiology. 2020 Mar; 128(3):828-839. doi: 10.1111/jam.14523. [PMID: 31755153]
  • Armelle Vigouroux, Abbas El Sahili, Julien Lang, Magali Aumont-Nicaise, Yves Dessaux, Denis Faure, Solange Moréra. Structural basis for high specificity of octopine binding in the plant pathogen Agrobacterium tumefaciens. Scientific reports. 2017 12; 7(1):18033. doi: 10.1038/s41598-017-18243-8. [PMID: 29269740]
  • Julien Lang, Armelle Vigouroux, Abbas El Sahili, Anthony Kwasiborski, Magali Aumont-Nicaise, Yves Dessaux, Jacqui Anne Shykoff, Solange Moréra, Denis Faure. Fitness costs restrict niche expansion by generalist niche-constructing pathogens. The ISME journal. 2017 02; 11(2):374-385. doi: 10.1038/ismej.2016.137. [PMID: 27801902]
  • Benoît Lacroix, Vitaly Citovsky. Nopaline-type Ti plasmid of Agrobacterium encodes a VirF-like functional F-box protein. Scientific reports. 2015 Nov; 5(?):16610. doi: 10.1038/srep16610. [PMID: 26586289]
  • Seiya Watanabe, Rui Sueda, Fumiyasu Fukumori, Yasuo Watanabe. Characterization of Flavin-Containing Opine Dehydrogenase from Bacteria. PloS one. 2015; 10(9):e0138434. doi: 10.1371/journal.pone.0138434. [PMID: 26382958]
  • Samuel Mondy, Aurore Lenglet, Amelie Beury-Cirou, Celestin Libanga, Pascal Ratet, Denis Faure, Yves Dessaux. An increasing opine carbon bias in artificial exudation systems and genetically modified plant rhizospheres leads to an increasing reshaping of bacterial populations. Molecular ecology. 2014 Oct; 23(19):4846-61. doi: 10.1111/mec.12890. [PMID: 25145455]
  • Ana Lidia Flores-Mireles, Anatol Eberhard, Stephen C Winans. Agrobacterium tumefaciens can obtain sulphur from an opine that is synthesized by octopine synthase using S-methylmethionine as a substrate. Molecular microbiology. 2012 Jun; 84(5):845-56. doi: 10.1111/j.1365-2958.2012.08061.x. [PMID: 22486934]
  • Thomas G Platt, Clay Fuqua, James D Bever. Resource and competitive dynamics shape the benefits of public goods cooperation in a plant pathogen. Evolution; international journal of organic evolution. 2012 Jun; 66(6):1953-65. doi: 10.1111/j.1558-5646.2011.01571.x. [PMID: 22671559]
  • Rui Rosa, Marta S Pimentel, Joana Boavida-Portugal, Tatiana Teixeira, Katja Trübenbach, Mário Diniz. Ocean warming enhances malformations, premature hatching, metabolic suppression and oxidative stress in the early life stages of a keystone squid. PloS one. 2012; 7(6):e38282. doi: 10.1371/journal.pone.0038282. [PMID: 22701620]
  • John Zupan, Cheryl A Hackworth, Julieta Aguilar, Doyle Ward, Patricia Zambryski. VirB1* promotes T-pilus formation in the vir-Type IV secretion system of Agrobacterium tumefaciens. Journal of bacteriology. 2007 Sep; 189(18):6551-63. doi: 10.1128/jb.00480-07. [PMID: 17631630]
  • Anja Brencic, Esther R Angert, Stephen C Winans. Unwounded plants elicit Agrobacterium vir gene induction and T-DNA transfer: transformed plant cells produce opines yet are tumour free. Molecular microbiology. 2005 Sep; 57(6):1522-31. doi: 10.1111/j.1365-2958.2005.04763.x. [PMID: 16135221]
  • Brian G Ayre, Felix Keller, Robert Turgeon. Symplastic continuity between companion cells and the translocation stream: long-distance transport is controlled by retention and retrieval mechanisms in the phloem. Plant physiology. 2003 Apr; 131(4):1518-28. doi: 10.1104/pp.012054. [PMID: 12692312]
  • Reiko Akakura, Stephen C Winans. Mutations in the occQ operator that decrease OccR-induced DNA bending do not cause constitutive promoter activity. The Journal of biological chemistry. 2002 May; 277(18):15773-80. doi: 10.1074/jbc.m200109200. [PMID: 11877409]
  • Hounayda Mansouri, Annik Petit, Phil Oger, Yves Dessaux. Engineered rhizosphere: the trophic bias generated by opine-producing plants is independent of the opine type, the soil origin, and the plant species. Applied and environmental microbiology. 2002 May; 68(5):2562-6. doi: 10.1128/aem.68.5.2562-2566.2002. [PMID: 11976135]
  • Reiko Akakura, Stephen C Winans. Constitutive mutations of the OccR regulatory protein affect DNA bending in response to metabolites released from plant tumors. The Journal of biological chemistry. 2002 Feb; 277(8):5866-74. doi: 10.1074/jbc.m110555200. [PMID: 11717314]
  • A Krishnamohan, V Balaji, K Veluthambi. Efficient vir gene induction in Agrobacterium tumefaciens requires virA, virG, and vir box from the same Ti plasmid. Journal of bacteriology. 2001 Jul; 183(13):4079-89. doi: 10.1128/jb.183.13.4079-4089.2001. [PMID: 11395473]
  • B Schrammeijer, A Beijersbergen, K B Idler, L S Melchers, D V Thompson, P J Hooykaas. Sequence analysis of the vir-region from Agrobacterium tumefaciens octopine Ti plasmid pTi15955. Journal of experimental botany. 2000 Jun; 51(347):1167-9. doi: 10.1093/jexbot/51.347.1167. [PMID: 10948245]
  • V S Kalogeraki, S C Winans. Wound-released chemical signals may elicit multiple responses from an Agrobacterium tumefaciens strain containing an octopine-type Ti plasmid. Journal of bacteriology. 1998 Nov; 180(21):5660-7. doi: 10.1128/jb.180.21.5660-5667.1998. [PMID: 9791116]
  • J D Palumbo, D A Phillips, C I Kado. Characterization of a new Agrobacterium tumefaciens strain from alfalfa. Archives of microbiology. 1998 May; 169(5):381-6. doi: 10.1007/s002030050586. [PMID: 9560417]
  • M Sato, T Nakano, M Takeuchi, N Kanno, E Nagahisa, Y Sato, Y Kobatake. Effects of octopine on the serum cholesterol level in rats. Bioscience, biotechnology, and biochemistry. 1996 Jan; 60(1):154-6. doi: 10.1271/bbb.60.154. [PMID: 8824838]
  • L Wang, S C Winans. The sixty nucleotide OccR operator contains a subsite essential and sufficient for OccR binding and a second subsite required for ligand-responsive DNA bending. Journal of molecular biology. 1995 Nov; 253(5):691-702. doi: 10.1006/jmbi.1995.0583. [PMID: 7473744]
  • D Kreusch, J von Lintig, J Schröder. Ti plasmid-encoded octopine and nopaline catabolism in Agrobacterium: specificities of the LysR-type regulators OccR and NocR, and protein-induced DNA bending. Molecular & general genetics : MGG. 1995 Nov; 249(1):102-10. doi: 10.1007/bf00290241. [PMID: 8552026]
  • S Q Pan, S Jin, M I Boulton, M Hawes, M P Gordon, E W Nester. An Agrobacterium virulence factor encoded by a Ti plasmid gene or a chromosomal gene is required for T-DNA transfer into plants. Molecular microbiology. 1995 Jul; 17(2):259-69. doi: 10.1111/j.1365-2958.1995.mmi_17020259.x. [PMID: 7494475]
  • V S Kalogeraki, S C Winans. The octopine-type Ti plasmid pTiA6 of Agrobacterium tumefaciens contains a gene homologous to the chromosomal virulence gene acvB. Journal of bacteriology. 1995 Feb; 177(4):892-7. doi: 10.1128/jb.177.4.892-897.1995. [PMID: 7860597]
  • E Mansur, C Lacorte, W R Krul. Peanut transformation. Methods in molecular biology (Clifton, N.J.). 1995; 44(?):87-100. doi: 10.1385/0-89603-302-3:87. [PMID: 7581687]
  • P Dion, C Bélanger, D Xu, M Mohammadi. Effect of acetosyringone on growth and oncogenic potential of Agrobacterium tumefaciens. Methods in molecular biology (Clifton, N.J.). 1995; 44(?):37-45. doi: 10.1385/0-89603-302-3:37. [PMID: 7581680]
  • H Zanker, G Lurz, U Langridge, P Langridge, D Kreusch, J Schröder. Octopine and nopaline oxidases from Ti plasmids of Agrobacterium tumefaciens: molecular analysis, relationship, and functional characterization. Journal of bacteriology. 1994 Aug; 176(15):4511-7. doi: 10.1128/jb.176.15.4511-4517.1994. [PMID: 8045881]
  • J von Lintig, D Kreusch, J Schröder. Opine-regulated promoters and LysR-type regulators in the nopaline (noc) and octopine (occ) catabolic regions of Ti plasmids of Agrobacterium tumefaciens. Journal of bacteriology. 1994 Jan; 176(2):495-503. doi: 10.1128/jb.176.2.495-503.1994. [PMID: 8288543]
  • M van Nuenen, P de Ruffray, L Otten. Rapid divergence of Agrobacterium vitis octopine-cucumopine Ti plasmids from a recent common ancestor. Molecular & general genetics : MGG. 1993 Jul; 240(1):49-57. doi: 10.1007/bf00276883. [PMID: 8101965]
  • F Paulus, L Otten. Functional and mutated agrocinopine synthase genes on octopine T-DNAs. Molecular plant-microbe interactions : MPMI. 1993 May; 6(3):393-402. doi: 10.1094/mpmi-6-393. [PMID: 8324252]
  • D M Raineri, M I Boulton, J W Davies, E W Nester. VirA, the plant-signal receptor, is responsible for the Ti plasmid-specific transfer of DNA to maize by Agrobacterium. Proceedings of the National Academy of Sciences of the United States of America. 1993 Apr; 90(8):3549-53. doi: 10.1073/pnas.90.8.3549. [PMID: 8475103]
  • C E Shurvinton, L Hodges, W Ream. A nuclear localization signal and the C-terminal omega sequence in the Agrobacterium tumefaciens VirD2 endonuclease are important for tumor formation. Proceedings of the National Academy of Sciences of the United States of America. 1992 Dec; 89(24):11837-41. doi: 10.1073/pnas.89.24.11837. [PMID: 1465407]
  • R H Valdivia, L Wang, S C Winans. Characterization of a putative periplasmic transport system for octopine accumulation encoded by Agrobacterium tumefaciens Ti plasmid pTiA6. Journal of bacteriology. 1991 Oct; 173(20):6398-405. doi: 10.1128/jb.173.20.6398-6405.1991. [PMID: 1655707]
  • L F Habeeb, L Wang, S C Winans. Transcription of the octopine catabolism operon of the Agrobacterium tumor-inducing plasmid pTiA6 is activated by a LysR-type regulatory protein. Molecular plant-microbe interactions : MPMI. 1991 Jul; 4(4):379-85. doi: 10.1094/mpmi-4-379. [PMID: 1799699]
  • J von Lintig, H Zanker, J Schröder. Positive regulators of opine-inducible promoters in the nopaline and octopine catabolism regions of Ti plasmids. Molecular plant-microbe interactions : MPMI. 1991 Jul; 4(4):370-8. doi: 10.1094/mpmi-4-370. [PMID: 1799698]
  • F Paulus, J Canaday, F Vincent, G Bonnard, C Kares, L Otten. Sequence of the iaa and ipt region of different Agrobacterium tumefaciens biotype III octopine strains: reconstruction of octopine Ti plasmid evolution. Plant molecular biology. 1991 Apr; 16(4):601-14. doi: 10.1007/bf00023425. [PMID: 1868199]
  • T R Steck, T S Lin, C I Kado. VirD2 gene product from the nopaline plasmid pTiC58 has at least two activities required for virulence. Nucleic acids research. 1990 Dec; 18(23):6953-8. doi: 10.1093/nar/18.23.6953. [PMID: 2263456]
  • K Shirasu, P Morel, C I Kado. Characterization of the virB operon of an Agrobacterium tumefaciens Ti plasmid: nucleotide sequence and protein analysis. Molecular microbiology. 1990 Jul; 4(7):1153-63. doi: 10.1111/j.1365-2958.1990.tb00690.x. [PMID: 2233252]
  • G A Kuldau, G De Vos, J Owen, G McCaffrey, P Zambryski. The virB operon of Agrobacterium tumefaciens pTiC58 encodes 11 open reading frames. Molecular & general genetics : MGG. 1990 Apr; 221(2):256-66. doi: 10.1007/bf00261729. [PMID: 2370849]
  • L S Melchers, M J Maroney, A den Dulk-Ras, D V Thompson, H A van Vuuren, R A Schilperoort, P J Hooykaas. Octopine and nopaline strains of Agrobacterium tumefaciens differ in virulence; molecular characterization of the virF locus. Plant molecular biology. 1990 Feb; 14(2):249-59. doi: 10.1007/bf00018565. [PMID: 2101693]
  • P Morel, B S Powell, P M Rogowsky, C I Kado. Characterization of the virA virulence gene of the nopaline plasmid, pTiC58, of Agrobacterium tumefaciens. Molecular microbiology. 1989 Sep; 3(9):1237-46. doi: 10.1111/j.1365-2958.1989.tb00274.x. [PMID: 2796735]
  • U Schindler, N Sans, J Schröder. Ornithine cyclodeaminase from octopine Ti plasmid Ach5: identification, DNA sequence, enzyme properties, and comparison with gene and enzyme from nopaline Ti plasmid C58. Journal of bacteriology. 1989 Feb; 171(2):847-54. doi: 10.1128/jb.171.2.847-854.1989. [PMID: 2644238]
  • R C Tait, C I Kado. Regulation of the virC and virD promoters of pTiC58 by the ros chromosomal mutation of Agrobacterium tumefaciens. Molecular microbiology. 1988 May; 2(3):385-92. doi: 10.1111/j.1365-2958.1988.tb00043.x. [PMID: 2840554]
  • B S de Pater, M P Klinkhamer, P A Amesz, R J de Kam, J Memelink, J H Hoge, R A Schilperoort. Plant expression signals of the Agrobacterium T-cyt gene. Nucleic acids research. 1987 Oct; 15(20):8267-81. doi: 10.1093/nar/15.20.8267. [PMID: 3671083]
  • B S de Pater, R J de Kam, J H Hoge, R A Schilperoort. Effects of mutations in the TATA box region of the Agrobacterium T-cyt gene on its transcription in plant tissues. Nucleic acids research. 1987 Oct; 15(20):8283-92. doi: 10.1093/nar/15.20.8283. [PMID: 3671084]
  • A C Yun, R G Hadley, A A Szalay. A plasmid sequence from Rhizobium leguminosarum 300 contains homology to sequences near the octopine TL-DNA right border. Molecular & general genetics : MGG. 1987 Oct; 209(3):580-4. doi: 10.1007/bf00331166. [PMID: 17193713]
  • N S Yang, S G Platt, P Christou. Detection of opines by colorimetric assay. Analytical biochemistry. 1987 Feb; 160(2):342-5. doi: 10.1016/0003-2697(87)90057-1. [PMID: 3578760]
  • L S Melchers, D V Thompson, K B Idler, R A Schilperoort, P J Hooykaas. Nucleotide sequence of the virulence gene virG of the Agrobacterium tumefaciens octopine Ti plasmid: significant homology between virG and the regulatory genes ompR, phoB and dye of E. coli. Nucleic acids research. 1986 Dec; 14(24):9933-42. doi: 10.1093/nar/14.24.9933. [PMID: 3027669]
  • E E Hood, G L Helmer, R T Fraley, M D Chilton. The hypervirulence of Agrobacterium tumefaciens A281 is encoded in a region of pTiBo542 outside of T-DNA. Journal of bacteriology. 1986 Dec; 168(3):1291-301. doi: 10.1128/jb.168.3.1291-1301.1986. [PMID: 3782037]
  • M F Yanofsky, E W Nester. Molecular characterization of a host-range-determining locus from Agrobacterium tumefaciens. Journal of bacteriology. 1986 Oct; 168(1):244-50. doi: 10.1128/jb.168.1.244-250.1986. [PMID: 3759904]
  • M R Davey, K M Gartland, B J Mulligan. Transformation of the genomic expression of plant cells. Symposia of the Society for Experimental Biology. 1986; 40(?):85-120. doi: ". [PMID: 3544312]
  • D Ursic. Eight DNA insertion events of Agrobacterium tumefaciens Ti-plasmids in isogenic sunflower genomes are all distinct. Biochemical and biophysical research communications. 1985 Aug; 131(1):152-9. doi: 10.1016/0006-291x(85)91783-8. [PMID: 3929775]
  • R Deblaere, B Bytebier, H De Greve, F Deboeck, J Schell, M Van Montagu, J Leemans. Efficient octopine Ti plasmid-derived vectors for Agrobacterium-mediated gene transfer to plants. Nucleic acids research. 1985 Jul; 13(13):4777-88. doi: 10.1093/nar/13.13.4777. [PMID: 4022773]
  • S E Stachel, G An, C Flores, E W Nester. A Tn3 lacZ transposon for the random generation of beta-galactosidase gene fusions: application to the analysis of gene expression in Agrobacterium. The EMBO journal. 1985 Apr; 4(4):891-8. doi: 10.1002/j.1460-2075.1985.tb03715.x. [PMID: 2990912]
  • W W Kwok, E W Nester, M P Gordon. Unusual plasmid DNA organization in an octopine crown gall tumor. Nucleic acids research. 1985 Jan; 13(2):459-71. doi: 10.1093/nar/13.2.459. [PMID: 4000924]
  • L Le Goff, M Beljanski. The in vitro effects of opines and other compounds on DNAs originating from bacteria, and from healthy and tumorous plant tissues. Experimental cell biology. 1985; 53(6):335-50. doi: 10.1159/000163331. [PMID: 3935498]
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  • V Knauf, M Yanofsky, A Montoya, E Nester. Physical and functional map of an Agrobacterium tumefaciens tumor-inducing plasmid that confers a narrow host range. Journal of bacteriology. 1984 Nov; 160(2):564-8. doi: 10.1128/jb.160.2.564-568.1984. [PMID: 6094476]
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  • P J Hooykaas, M Hofker, H den Dulk-Ras, R A Schilperoort. A comparison of virulence determinants in an octopine Ti plasmid, a nopaline Ti plasmid, and an Ri plasmid by complementation analysis of Agrobacterium tumefaciens mutants. Plasmid. 1984 May; 11(3):195-205. doi: 10.1016/0147-619x(84)90026-x. [PMID: 6087390]
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  • K Lahners, M C Byrne, M D Chilton. T-DNA fragments of hairy root plasmid pRi8196 are distantly related to octopine and nopaline Ti plasmid T-DNA. Plasmid. 1984 Mar; 11(2):130-40. doi: 10.1016/0147-619x(84)90018-0. [PMID: 6328555]
  • C Lichtenstein, H Klee, A Montoya, D Garfinkel, S Fuller, C Flores, E Nester, M Gordon. Nucleotide sequence and transcript mapping of the tmr gene of the pTiA6NC octopine Ti-plasmid: a bacterial gene involved in plant tumorigenesis. Journal of molecular and applied genetics. 1984; 2(4):354-62. doi: ". [PMID: 6330262]
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  • P Dhaese, H De Greve, J Gielen, L Seurinck, M Van Montagu, J Schell. Identification of sequences involved in the polyadenylation of higher plant nuclear transcripts using Agrobacterium T-DNA genes as models. The EMBO journal. 1983; 2(3):419-26. doi: 10.1002/j.1460-2075.1983.tb01439.x. [PMID: 11894958]
  • G Ooms, A Bakker, L Molendijk, G J Wullems, M P Gordon, E W Nester, R A Schilperoort. T-DNA organization in homogeneous and heterogeneous octopine-type crown gall tissues of Nicotiana tabacum. Cell. 1982 Sep; 30(2):589-97. doi: 10.1016/0092-8674(82)90255-0. [PMID: 6291777]
  • R K Prakash, R A Schilperoort. Relationship between Nif plasmids of fast-growing Rhizobium species and Ti plasmids of Agrobacterium tumefaciens. Journal of bacteriology. 1982 Mar; 149(3):1129-34. doi: 10.1128/jb.149.3.1129-1134.1982. [PMID: 7061382]
  • B P Koekman, P J Hooykaas, R A Schilperoort. A functional map of the replicator region of the octopine Ti plasmid. Plasmid. 1982 Mar; 7(2):119-32. doi: 10.1016/0147-619x(82)90072-5. [PMID: 6281832]
  • J Hille, I Klasen, R Schilperoort. Construction and application of R prime plasmids, carrying different segments of an octopine Ti plasmid from Agrobacterium tumefaciens, for complementation of vir genes. Plasmid. 1982 Mar; 7(2):107-18. doi: 10.1016/0147-619x(82)90071-3. [PMID: 6281831]
  • M W Bevan, M D Chilton. T-DNA of the Agrobacterium Ti and Ri plasmids. Annual review of genetics. 1982; 16(?):357-84. doi: 10.1146/annurev.ge.16.120182.002041. [PMID: 6297376]
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