Biosynthesis of phloroglucinol and preparation of 1,3-dihydroxybenzene therefrom
A phloroglucinol, biosynthetic technology, used in the preparation of organic compounds, active ingredients of hydroxyl compounds, aldehyde/ketone condensation polymer binders, etc.
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[0089] Phloroglucinol (1a, Scheme 1, ie Figure 1) was found as a substituent in various natural products. However, the biosynthesis of phloroglucinol 1a as an independent molecule has not been described. As part of this biosynthetic activity study, acetylphloroglucinol formed in Pseudomonas fluorescens Pf-5 was analyzed (6 and 7, Scheme 1). B. Novak-Thompson et al., Can. J. Microbiol. 40:1064 (1994). Phloroglucinol biosynthesis was examined. Later heterologous expression of Pseudomonas fluorescens phlD resulted in the accumulation of phloroglucinol 1a in E. coli cultures. In addition to inferences about the biosynthesis of acetylphloroglucinol, these findings establish the basis for a new environmentally benign synthesis of phloroglucinol and resorcinol.
[0090]Activated 3,5-diketonhexanoate (diketonhexanoate) 2 (i.e., activated 3,5-diketocaproate (3,5-diketocaproate)) is probably the two structurally simplest polyketide natural Products, precursors of phloroglucinol 1a a...
Embodiment 2
[0105] Example 2. Expression of PhlD in E.coli and the resulting synthesis of phloroglucinol
[0106] Plasmid pJA3.131 (Kan R ,lacI Q , P T7 -phlD, serA) was chromosomally transfected into serA - E. coli strains BL21(DE3), W3110(DE3), and JWF1(DE3) [ie, RB791serA -(DE3)], and in strain KL3(DE3) [ie AB2834(serA::aroB)] (E. coli strains RB791 and AB2834 are available from the E. coli GeneticStock Center in New Haven, Connecticut, USA) . All DE3 strains were obtained by integrating the λDE3 prophage into the cell chromosome.
[0107] Cells were grown in fed-batch mode in mineral salts and limited glucose. Although all transformed strains expressed abundant levels of phloroglucinol, the BL21 and W3110 strains produced higher titers of 3.0 and 3.1 g / L phloroglucinol, respectively; These strains produced higher phloroglucinol yields of 4.4 and 3.1 mol phloroglucinol per 100 mol glucose (% mol / mol).
[0108] These experiments also compared the same use of phlD in Ptac or P T...
Embodiment 3
[0109] Example 3. Extracted phloroglucinol fermentation
[0110] Anion-exchange resin column-based extractive fermentation was used to remove phloroglucinol to reduce or eliminate its cytotoxicity and inhibition of phloroglucinol synthesis during fermentation. The shaking box reactor was equipped with tubing leading into the anion exchange column and back to the shaking box; the tubing was equipped with a peristaltic pump to circulate the matrix through the column. A Bio-Rad Econo column (25×200mm) equipped with 80mL (column bed volume) AG1-X8 resin was used with 15 column bed volumes of KH 2 PO 4 (0.8M) to convert the tertiary ammonium salts to the phosphate form prior to in situ extraction. A total of 3 to 5 columns were used per fermentation; each column was used for about 6-12 hours before being replaced with another column to keep the phloroglucinol concentration in the medium below about 1.5 g / L. All columns were operated in fluidized bed mode and their circulation fl...
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