Acaterin

Acaterin

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Acaterin
Category Enzyme inhibitors
Catalog number BBF-00539
CAS 144398-20-9
Molecular Weight 226.31
Molecular Formula C13H22O3
Purity >98%

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Description

Acarbose is an acyl-CoA isolated from Pseudomonas species. A92. In the presence of oxidized low-density lipoprotein in macrophages J744, the synthesis of cholesterol enzymes is inhibited, with an IC50 of 45 µmol/L, and the IC50 for inhibiting ACAT in rat liver microsomes is 120 µmol/L. Inhibition of ACAT is non-competitive Sexual.

Specification

Synonyms (2R)-4-[(1R)-1-hydroxyoctyl]-2-methyl-2H-furan-5-one; 3-(1-Hydroxyoctyl)-5-methyl-2(5H)-furanone
Storage Store at -20°C
IUPAC Name (2R)-4-[(1R)-1-hydroxyoctyl]-2-methyl-2H-furan-5-one
Canonical SMILES CCCCCCCC(C1=CC(OC1=O)C)O
InChI InChI=1S/C13H22O3/c1-3-4-5-6-7-8-12(14)11-9-10(2)16-13(11)15/h9-10,12,14H,3-8H2,1-2H3/t10-,12-/m1/s1
InChI Key YUMHJXLSSASJGN-ZYHUDNBSSA-N

Properties

Appearance Light Brown Oil
Boiling Point 382.4°C at 760 mmHg
Density 1.03 g/cm3
Solubility Soluble in DMSO

Reference Reading

1. Biosynthesis of Pseudomonas-Derived Butenolides
Martin Klapper, Kevin Schlabach, André Paschold, Shuaibing Zhang, Somak Chowdhury, Klaus-Dieter Menzel, Miriam A Rosenbaum, Pierre Stallforth Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5607-5610. doi: 10.1002/anie.201914154. Epub 2020 Jan 29.
Butenolides are well-known signaling molecules in Gram-positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram-negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas-derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.
2. Biosynthesis of acaterin: mechanism of the reaction catalyzed by dehydroacaterin reductase
Sayaka Nakano, Wataru Sakane, Hiroshi Oinaka, Yoshinori Fujimoto Bioorg Med Chem. 2006 Sep 15;14(18):6404-8. doi: 10.1016/j.bmc.2006.05.039. Epub 2006 Jun 9.
Dehydroacaterin reductase is an enzyme which catalyzes the final step of acaterin biosynthesis, that is, the reduction of the C-4/C-5 double bond of dehydroacaterin. The mechanism of the reduction was investigated with a cell-free preparation obtained from the acaterin-producing microorganism, Pseudomonas sp. A 92. Incubation of dehydroacaterin in the presence of [4,4- 2H2]NADPH or D2O followed by 2H NMR analysis of the resulting acaterin revealed that the deuterium atom from NADPH was incorporated into the C-5 position of acaterin, while the deuterium atom from D2O was introduced into the C-4 position. It was further demonstrated that the pro-R hydrogen at C-4 of NADPH was stereospecifically utilized in this reduction.
3. Isolation and structure elucidation of Peronosporomycetes hyphal branching-inducing factors produced by Pseudomonas jessenii EC-S101
Eduardo Hatano, Yasuyuki Hashidoko, Abhinandan Deora, Yukiharu Fukushi, Satoshi Tahara Biosci Biotechnol Biochem. 2007 Jun;71(6):1601-5. doi: 10.1271/bbb.70119.
Pseudomonas jessenii EC-S101 produced hyphal branching-inducing and mitosis-accelerating factors active towards Peronosporomycetes, Aphanomyces cochlioides hyphae. In searching for the active substances, EtOAc-solubles extracted from EC-S101-cultured solid medium were fractionated under the guidance of a paper disc assay using an A. cochlioides mycelium. Two active substances were subsequently isolated and the structure was elucidated by spectroscopic analysis to be (+)-4,5-didehydroacaterin (1) and 3-[(1R)-hydroxyhexyl]-5-methylene-2(5H)-furanone (2), both of which accelerated the mitotic process of A. cochlioides hyphae along with excessive branching at 1.0 microg per disc. These compounds are likely to affect the morphophysiological development of certain eukaryotic organisms in the terrestrial ecosystem.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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