Agrocin 84
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00392 |
| CAS | 59111-78-3 |
| Molecular Weight | 702.50 |
| Molecular Formula | C22H36N6O16P2 |
Online Inquiry
Description
It is produced by the strain of Agrobacterium radiobacter. It can inhibit DNA synthesis, and sterilize Agrobacterium Tume Faciens.
Specification
| Synonyms | Agrocin; D-Glucofuranose,1-[hydrogen[9-[3-deoxy-5-O-[[(4,5-dideoxy-4-methyl-D-threo-pentonoyl)amino]hydroxyphosphinyl]-b-D-threo-pentofuranosyl]-9H-purin-6-yl]phosphoramidate]; Mono-D-glucofuranosyl[9-[3-deoxy-5-O-[[(4,5-dideoxy-4-methyl-D-threo-pentonoyl)amino]hydroxyphosphinyl]-b-D-threo-pentofuranosyl]-9H-purin-6-yl]phosphoramidate |
| IUPAC Name | [(3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-N-[9-[(3S,5S)-5-[[[[(2S,3R)-2,3-dihydroxy-4-methylpentanoyl]amino]-hydroxyphosphoryl]oxymethyl]-3-hydroxyoxolan-2-yl]purin-6-yl]phosphonamidic acid |
| Canonical SMILES | CC(C)C(C(C(=O)NP(=O)(O)OCC1CC(C(O1)N2C=NC3=C(N=CN=C32)NP(=O)(O)OC4C(C(C(O4)C(CO)O)O)O)O)O)O |
| InChI | InChI=1S/C22H36N6O16P2/c1-8(2)13(32)15(34)20(36)27-45(37,38)41-5-9-3-10(30)21(42-9)28-7-25-12-18(23-6-24-19(12)28)26-46(39,40)44-22-16(35)14(33)17(43-22)11(31)4-29/h6-11,13-17,21-22,29-35H,3-5H2,1-2H3,(H2,27,36,37,38)(H2,23,24,26,39,40)/t9-,10-,11+,13+,14+,15-,16+,17-,21?,22?/m0/s1 |
| InChI Key | FIMRCGIHIAIVOL-DUQSPLRMSA-N |
Properties
| Density | 2.070 g/cm3 |
Reference Reading
1. 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
H Kim, S K Farrand J Bacteriol. 1997 Dec;179(23):7559-72. doi: 10.1128/jb.179.23.7559-7572.1997.
The acc locus from the Ti plasmid pTiC58 confers utilization of and chemotaxis toward agrocinopines A and B (A+B), as well as susceptibility to a highly specific antiagrobacterial antibiotic, agrocin 84. DNA sequence analyses revealed that acc is composed of eight open reading frames, accR and accA through accG. Previous work showed that accR encodes the repressor which regulates this locus, and accA codes for the periplasmic binding protein of the agrocinopine transport system (S. Beck Von Bodman, G. T. Hayman, and S. K. Farrand, Proc. Natl. Acad. Sci. USA 89:643-647, 1992; G. T. Hayman, S. Beck Von Bodman, H. Kim, P. Jiang, and S. K. Farrand, J. Bacteriol. 175:5575-5584, 1993). The predicted proteins from accA through accE, as a group, have homology to proteins that belong to the ABC-type transport system superfamily. The predicted product of accF is related to UgpQ of Escherichia coli, which is a glycerophosphoryl diester phosphodiesterase, and also to agrocinopine synthase coded for by acs located on the T-DNA. The translated product of accG is related to myoinositol 1 (or 4) monophosphatases from various eucaryotes. Analyses of insertion mutations showed that accA through accE are required for transport of both agrocin 84 and agrocinopines A+B, while accF and accG are required for utilization of the opines as the sole source of carbon. Mutations in accF or accG did not abolish transport of agrocin 84, although we observed slower removal of the antibiotic from the medium by the accF mutant compared to the wild type. However, the insertion mutation in accF abolished detectable uptake of agrocinopines A+B. A mutation in accG had no effect on transport of the opines. The accF mutant was not susceptible to agrocin 84 although it took up the antibiotic. This finding suggests that agrocin 84 is activated by AccF after being transported into the bacterial cell.
2. Characterization and mapping of the agrocinopine-agrocin 84 locus on the nopaline Ti plasmid pTiC58
G T Hayman, S K Farrand J Bacteriol. 1988 Apr;170(4):1759-67. doi: 10.1128/jb.170.4.1759-1767.1988.
Overlapping segments of pTiC58 inserted into cosmid vectors were used to characterize the agrocinopine-agrocin 84 locus from the nopaline/agrocinopine A and B Agrobacterium tumefaciens strain C58. All of the clones conferring agrocin 84 sensitivity on agrobacteria also conferred uptake of agrocin 84 and agrocinopines A and B. Transposon Tn3-HoHo1 insertion mutations of one such clone were generated that simultaneously abolished agrocin 84 sensitivity and transport of agrocinopines A and B and agrocin 84. Such insertions were found to cluster within a 4.4-kilobase region. Analysis of beta-galactosidase activity in these insertion mutants suggested a single transcriptional unit regulated at the transcriptional level by agrocinopines A and B. The smallest DNA fragment subcloned from the region to confer all three activities was 8.5 kilobases long. This subclone was still properly regulated, indicating that the regulatory gene is closely linked to the locus. The data are consistent with a single operon encoding catabolism of agrocinopines A and B and conferring sensitivity to agrocin 84. Based on these results, we support the locus name acc, for agrocinopine catabolism.
3. Esters of Glucose-2-Phosphate: Occurrence and Chemistry
Qiang Zhang, Si-Zhe Li, Mohammed Ahmar, Laurent Soulère, Yves Queneau Molecules. 2020 Jun 19;25(12):2829. doi: 10.3390/molecules25122829.
Phosphodiesters of glucose-2-phosphate (G2P) are found only in few natural compounds such as agrocinopine D and agrocin 84. Agrocinopine D is a G2P phosphodiester produced by plants infected by Agrobacterium fabrum C58 and recognized by the bacterial periplasmic binding protein AccA for being transported into the bacteria before cleavage by the phosphodiesterase AccF, releasing G2P, which promotes virulence by binding the repressor protein AccR. The G2P amide agrocin 84 is a natural antibiotic produced by the non-pathogenic Agrobacterium radiobacter K84 strain used as a biocontrol agent by competing with Agrobacterium fabrum C58. G2P esters are also found in irregular glycogen structures. The rare glucopyranosyl-2-phophoryl moiety found in agrocin 84 is the key structural signature enabling its action as a natural antibiotic. Likewise, G2P and G2P esters can also dupe the Agrobacterium agrocinopine catabolism cascade. Such observations illustrate the importance of G2P esters on which we have recently focused our interest. After a brief review of the reported phosphorylation coupling methods and the choice of carbohydrate building blocks used in G2P chemistry, a flexible access to glucose-2-phosphate esters using the phosphoramidite route is proposed.
Recommended Products
| BBF-03753 | Baicalin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01825 | Loganin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
