Agglomerin

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Agglomerin A
Agglomerin A.png
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
  • InChI=1S/C15H22O4/c1-3-4-5-6-7-8-9-10-12(16)13-14(17)11(2)19-15(13)18/h17H,2-10H2,1H3
    Key: YFNGFFUIVKWQHE-UHFFFAOYSA-N
  • O=C(C1=C(O)C(OC1=O)=C)CCCCCCCCC
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 their standard state (at 25 °C [77 °F], 100 kPa).

Agglomerins are bacterial natural products, identified as metabolites of Pantoea agglomerans which was isolated in 1989 from river water in Kobe, Japan.[1] They belong to the class of tetronate antibiotics, which include tetronomycin, tetronasin, and abyssomicin 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 bacteria in 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 7 open 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 intermediate 4 is 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]

Agglomerin biosynthesis – the biosynthesis of agglomerins A-D by Agg1, Agg2, Agg3, Agg4 and Agg5

References[edit]

  1. ^ 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. ISSN 0021-8820. PMID 2621155.
  2. ^ 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. ISSN 0021-8820. PMID 2258324.
  3. ^ Microbiology Abstracts: Bacteriology. Information Retrieval. 1990.
  4. ^ 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. PMID 18046685. S2CID 43868662.
  5. ^ 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. PMID 23606658.