Anguibactin
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| Category | Antibiotics |
| Catalog number | BBF-00470 |
| CAS | 104245-09-2 |
| Molecular Weight | 348.38 |
| Molecular Formula | C15H16N4O4S |
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Description
It is produced by the strain of Vibrio angullarum. It is an antibiotic that acts as a Siderophore and has a very strong affinity with Fe+3.
Specification
| Synonyms | (2Z)-N-hydroxy-2-(5-hydroxy-6-oxo-1-cyclohexa-2,4-dienylidene)-N-[2-(3H-imidazol-4-yl)ethyl]thiazolidine-4-carboxamide; ACMC-20m71m; (2Z)-N-hydroxy-2-(5-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)-N-[2-(1H-imidazol-5-yl)ethyl]-1,3-thiazolidine-4-carboxamide |
| IUPAC Name | 2-(2,3-dihydroxyphenyl)-N-hydroxy-N-[2-(1H-imidazol-5-yl)ethyl]-4,5-dihydro-1,3-thiazole-4-carboxamide |
| Canonical SMILES | C1C(N=C(S1)C2=C(C(=CC=C2)O)O)C(=O)N(CCC3=CN=CN3)O |
| InChI | InChI=1S/C15H16N4O4S/c20-12-3-1-2-10(13(12)21)14-18-11(7-24-14)15(22)19(23)5-4-9-6-16-8-17-9/h1-3,6,8,11,20-21,23H,4-5,7H2,(H,16,17) |
| InChI Key | GBKVAPJMXMGXJK-UHFFFAOYSA-N |
Properties
| Boiling Point | 766.4 °C at 760 mmHg |
| Density | 1.609 g/cm3 |
Reference Reading
1. Synthesis and Characterization of Anguibactin To Reveal Its Competence To Function as a Thermally Stable Surrogate Siderophore for a Gram-Negative Pathogen, Acinetobacter baumannii
Haeun Lee, Woon Young Song, Minju Kim, Min Wook Lee, Soojeung Kim, Ye Song Park, Kyungwon Kwak, Man Hwan Oh, Hak Joong Kim Org Lett. 2018 Oct 19;20(20):6476-6479. doi: 10.1021/acs.orglett.8b02789. Epub 2018 Oct 8.
Total synthesis of anguibactin was accomplished for the first time, and the following biochemical characterizations allowed for the determination of its Fe(III) binding mode as well as the demonstration of its iron delivery capability for Acinetobacter baumannii. These properties, in addition to the thermal stability over acinetobactin, render anguibactin as a competent surrogate siderophore that can be useful for the future development of a siderophore-based antibiotic delivery system against A. baumannii.
2. The anguibactin biosynthesis and transport genes are encoded in the chromosome of Vibrio harveyi: a possible evolutionary origin for the pJM1 plasmid-encoded system of Vibrio anguillarum?
Hiroaki Naka, Luis A Actis, Jorge H Crosa Microbiologyopen. 2013 Feb;2(1):182-94. doi: 10.1002/mbo3.65. Epub 2013 Jan 18.
Many Vibrio anguillarum serotype O1 strains carry 65-kb pJM1-type plasmids harboring genes involved in siderophore anguibactin biosynthesis and transport. The anguibactin system is an essential factor for V. anguillarum to survive under iron-limiting conditions, and as a consequence, it is a very important virulence factor of this bacterium. Our comparative analysis of genomic data identified a cluster harboring homologs of anguibactin biosynthesis and transport genes in the chromosome of Vibrio harveyi. We have purified the putative anguibactin siderophore and demonstrated that it is indeed anguibactin by mass spectrometry and specific bioassays. Furthermore, we characterized two genes, angR and fatA, in this chromosome cluster that, respectively, participate in anguibactin biosynthesis and transport as determined by mutagenesis analysis. Furthermore, we found that the V. harveyi FatA protein is located in the outer membrane fractions as previously demonstrated in V. anguillarum. Based on our data, we propose that the anguibactin biosynthesis and transport cluster in the V. anguillarum pJM1 plasmid have likely evolved from the chromosome cluster of V. harveyi or vice versa.
3. Plasmid- and chromosome-encoded siderophore anguibactin systems found in marine vibrios: biosynthesis, transport and evolution
Hiroaki Naka, Moqing Liu, Luis A Actis, Jorge H Crosa Biometals. 2013 Aug;26(4):537-47. doi: 10.1007/s10534-013-9629-z. Epub 2013 May 10.
Vibrio anguillarum is a marine pathogen that causes vibriosis, a hemorrhagic septicemia in aquatic invertebrate as well as vertebrate animals. The siderophore anguibactin system is one of the most important virulence factors of this bacterium. Most of the anguibactin biosynthesis and transport genes are located in the 65-kb pJM1 virulence plasmid although some of them are found in the chromosome of this fish pathogen. Over 30 years of research unveiled the role numerous chromosomal and pJM1 genes play in the synthesis of anguibactin and the transport of cognate ferric complexes into the bacterial cell. Furthermore, these studies showed that pJM1-carrying strains might be originated from pJM1-less strains producing the chromosome-mediated siderophore vanchrobactin. Additionally, we recently identified a chromosome-mediated anguibactin system in V. harveyi suggesting the possible evolutional origin of the V. anguillarum anguibactin system. In this review, we present our current understanding of the mechanisms and evolution hypothesis of the anguibactin system that might have occurred in these pathogenic vibrios.
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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 ╳
