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F-14329 Sale

(Synonyms: Tolypocladenol B) 目录号 : GC47329

A metal chelator

F-14329 Chemical Structure

Cas No.:942195-19-9

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1 mg
¥4,437.00
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产品描述

F-14329 is a tetramic acid fungal metabolite and a metal chelator that has been found in Chaunopycnis.1 It chelates iron, copper, magnesium, zinc, and aluminum ions in cell-free assays.

1.Shang, Z., Li, L., Esposito, B.P., et al.New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.Org. Biomol. Chem.13(28)7795-7802(2015)

Chemical Properties

Cas No. 942195-19-9 SDF
别名 Tolypocladenol B
Canonical SMILES O=C([C@@]([C@@H](O)C1=CC=C(O)C=C1)([H])NC/2=O)C2=C([C@H](C[C@@H](C)C/C=C/C)C)\O
分子式 C21H27NO5 分子量 373.4
溶解度 Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.6781 mL 13.3905 mL 26.7809 mL
5 mM 0.5356 mL 2.6781 mL 5.3562 mL
10 mM 0.2678 mL 1.339 mL 2.6781 mL
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Research Update

A Synthetic Route to β-Hydroxytyrosine-Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F-14329

Chemistry 2017 Apr 27;23(24):5692-5695.PMID:28345765DOI:10.1002/chem.201701259.

3-Acyltetramic acids derived from β-hydroxytyrosine are synthetically challenging. The first route to this structural motif, based upon a condensation between a Meldrum's acid conjugate bearing the acyl side chain, and a β-hydroxytyrosinate, N-protected by an ortho-nitrobenzyl group is presented. This group enables the Dieckmann cyclization of the resulting N-(β-ketoacyl)amino ester, after which it can be removed photolytically without compromising the delicate 3'-hydroxy group. This strategy was applied to the first total synthesis of the fungal metabolite F-14329 (1).

New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp

Org Biomol Chem 2015 Jul 28;13(28):7795-802.PMID:26107107DOI:10.1039/c5ob01058f.

Chemical analysis of a marine-derived fungus, Chaunopycnis sp. (CMB-MF028), isolated from the inner tissue of a pulmonate false limpet Siphonaria sp., collected from rock surfaces in the intertidal zone of Moora Park, Shorncliffe, Queensland, yielded the tetramic acid F-14329 (1) and new analogues, chaunolidines A-C (2-4), together with the new pyridinone chaunolidone A (5), and pyridoxatin (6). Structures inclusive of absolute configurations were assigned to 1-6 on the basis of detailed spectroscopic analysis, X-ray crystallography, electronic circular dichroism (ECD), biosynthetic considerations and chemical interconversion. Chaunolidine C (4) exhibits modest Gram-positive antibacterial activity (IC50 5-10 μM), while chaunolidone A (5) is a selective and potent inhibitor (IC50 0.09 μM) of human non-small cell lung carcinoma cells (NCI-H460). Tetramic acids 1-4 form metal chelates with Fe(III), Al(III), Cu(II), Mg(II) and Zn(II).