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Organic Letters

Volumn 9, Issue 13, 2007, Pages 2449-2451

Fumimycin: A peptide deformylase inhibitor with an unusual skeleton produced by Aspergillus fumisynnematus

(4) Kwon, Yun Ju a Sohn, Mi Jin a Zheng, Chang Ji a Kim, Won Gon a

a Korea Research Institute of Bioscience and Biotechnology (KRIBB) (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; BENZOFURAN DERIVATIVE; FUMIMYCIN; PEPTIDE DEFORMYLASE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; METABOLISM; STAPHYLOCOCCUS AUREUS;

AMIDOHYDROLASES; ASPERGILLUS; BENZOFURANS; MOLECULAR STRUCTURE; STAPHYLOCOCCUS AUREUS;

EID: 34547226538 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0703231 Document Type: Article

Times cited : (83)

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- The solate was identified as Aspergillus fumisynnematus Horie et al. 1993 on the basis of standard biological and physiological tests and taxonomic determination. Fermentation was carried out in liquid culture using YPS medium (2% glucose, 0.2% yeast extract, 0.5% peptone, 0.05% MgSO 4, and 0.1, KH2PO4, pH 5.7 before sterilization, A piece of a colony from a mature agar plate culture was inoculated into a 500-mL Erlenmeyer flask containing 80 mL of the above sterile seed liquid medium and cultured on a rotary shaker (150 rpm) at 28°C for 3 days. For the production of active compounds. 15 mL of the seed culture were transferred into 1000-mL Erlenmeyer flasks containing 300 mL of YPS medium and cultivated on a rotary shaker (150 rpm) for 7 days at 28°C
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- The culture broth (12 liters) was extracted with 50% aqueous acetone and evaporated to remove acetone. The resultant water phase was partitioned with an equal of EtOAc three times and the EtOAc layer was concentrated in vacuo. The resultant residue (4.39 g) was subjected to SiO2 (Merck Art No. 7734.9025) column chromatography using stepwise elution with CHCl 3-MeOH, 10:1, 5:1. 2:1. 1:1, The active fractions eluted with CHCl3-MeOH (1:1) were pooled and concentrated in vacuo to give an oily residue. The residue was applied to a Sephadex LH-20 column and then eluted with MeOH. The active fraction dissolved in MeOH was further purified by reversed-phase HPLC (20 × 250 mm, YMC C18) with a photodiode array detector. The column was eluted with MeOH-H2O (50: 50) containing 0.01%TFA at a flow rate of 3.5 mL/minute to afford 1 (11 mg) with a retention time of 28 minutes as a white powder. Compound 1: a white powder; λ
- 7Na requires 356.07407

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- A mixture of 2 mL MeOH, 0.04 mL H2SO4, and 5 mg fumimycin was stirred for 6 h at room temperature, poured into 50 mL water, and extracted twice with 50 mL EtOAc. The solvent of the organic layer was evaporated. The residue was subjected to preparative ODS TLC developed with 50% aqueous MeOH containing 0.01% TFA to yield a methylated product (2 mg, Fumimycin methyl ester: a white powder. ESI-MS: m/z 346.3 (M, H, 348.3 (M, H, 370.3 (M, Na, H NMR (300 MHz, CD3Cl, CD3OD, δ 6.95 (1H, d, 15.6. H-14, 6.65 (1H, d, 15.6, H-15, 6.62 (1H, dq, 16.2, 6.6. H-10, 6.51 (1H. s. H-4, 6.33 (1H, dq, 16.2, 1.2, H-9, 3.75 (3H, s, COOCH3, 1.89 (3H, dd, 6.6, 1.2, H-11, 1.65 (3H, s, H-8, 13C NMR (800 MHz, CD 3Cl, CD3OD) δ 177.0 (C-6, 166.2 (C-16, 163.1 (C-13, 145.6 (C-3, C-4a, 140.0 (C-2, 135.0 (C-14, 133.6 (C-10, 130.1 (C-15, 121.60-9
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