Agglomerin
![]() | |
Names | |
---|---|
Preferred IUPAC name
3-Decanoyl-4-hydroxy-5-methylidenefuran-2(5H)-one | |
Other names
3-[(Z)-1-hydroxydecylidene]-5-methylenetetrahydrofuran-2,4-dione
| |
Identifiers | |
3D model (JSmol)
|
|
ChEMBL | |
ChemSpider | |
PubChemCID
|
|
CompTox Dashboard(EPA)
|
|
| |
| |
Properties | |
C15H22O4 | |
Molar mass | 266.34 g/mol |
Appearance | Colorless crystalline powders (Na salt) |
Melting point | 113-115 (A), 85-88 (B), 125-128 (C), 103-106 (D) |
Insoluble (Na salt) | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
|
Agglomerinsarebacterialnatural products,identified asmetabolitesofPantoea agglomeranswhich was isolated in 1989 from river water inKobe,Japan.[1]They belong to the class of tetronate antibiotics, which includetetronomycin,tetronasin,andabyssomicin C.The members of the agglomerins differ only in the composition of the acyl chain attached to the tetronate ring. They possess antibiotic activity against anaerobic bacteria and weak activity against aerobic bacteriain vitro.The structures were solved in 1990.[2]Agglomerin A is the major component (38%), followed by agglomerin B (30%), agglomerin C (24%), and agglomerin D (8%).[3]
Biosynthesis
[edit]The biosynthetic gene cluster for agglomerins is 12 kb, and codes for 7open reading frames.The glyceryl-S-ACP is derived from D-1,3-bisphosphoglycerate by Agg2 (glyceryl-S-ACP synthase) and Agg3 (acyl carrier protein).[4]The acyl chain is taken from primary metabolism as a 3-oxoacyl-CoA thioester. The glyceryl-S-ACP and 3-oxoacyl-CoA thioester are joined by Agg1, a FabH-like ketosynthase, forming new C-C and C-O bonds. The primary alcohol of the intermediate4is then acylated by Agg4, using acetyl-CoA, before the abstraction of a proton and concomitant loss of acetate catalyzed by Agg5 to generate the exocyclic double bond.[5]
![](https://upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Agglomerin_Biosynthesis.png/800px-Agglomerin_Biosynthesis.png)
References
[edit]- ^Shoji, Jun'Ichi; Sakazaki, Ryuji; Hattori, Teruo; Matsumoto, Koichi; Uotani, Nobuo; Yoshida, Tadashi (1989)."Isolation and characterization of agglomerinsA, B, C and D."The Journal of Antibiotics.42(12): 1729–1733.doi:10.7164/antibiotics.42.1729.ISSN0021-8820.PMID2621155.
- ^Terui, Yoshihiro; Sakazaki, Ryuji; Shoji, Jun'Ichi (1990)."Structures of agglomerins".The Journal of Antibiotics.43(10): 1245–1253.doi:10.7164/antibiotics.43.1245.ISSN0021-8820.PMID2258324.
- ^Microbiology Abstracts: Bacteriology.Information Retrieval. 1990.
- ^Sun, Yuhui; Hong, Hui; Gillies, Fraser; Spencer, Jonathan B.; Leadlay, Peter F. (2008). "Glyceryl-S-Acyl Carrier Protein as an Intermediate in the Biosynthesis of Tetronate Antibiotics".ChemBioChem.9(1): 150–156.doi:10.1002/cbic.200700492.PMID18046685.S2CID43868662.
- ^Kanchanabanca, Chompoonik; Tao, Weixin; Hong, Hui; Liu, Yajing; Hahn, Frank; Samborskyy, Markiyan; Deng, Zixin; Sun, Yuhui; Leadlay, Peter F. (2013). "Unusual Acetylation-Elimination in the Formation of Tetronate Antibiotics".Angewandte Chemie International Edition.52(22): 5785–5788.doi:10.1002/anie.201301680.PMID23606658.