- Purification and characterization of molybdenum-containing aldehyde dehydrogenase that oxidizes benzyl maltol derivative from Pseudomonas nitroreducens SB32154
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Maltol derivatives are used in a variety of fields due to their metal-chelating abilities. In the previous study, it was found that cytochrome P450 monooxygenase, P450nov, which has the ability to effectively convert the 2-methyl group in a maltol derivative, transformed 3-benzyloxy-2-methyl-4-pyrone (BMAL) to 2-(hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one (BMAL-OH) and slightly to 3-benzyloxy-4-oxo-4 H-pyran-2-carboxaldehyde (BMAL-CHO). We isolated Pseudomonas nitroreducens SB32154 with the ability to convert BMAL-CHO to BMAL-COOH from soil. The enzyme responsible for aldehyde oxidation, a BMAL-CHO dehydrogenase, was purified from P. nitroreducens SB32154 and characterized. The purified BMAL-CHO dehydrogenase was found to be a xanthine oxidase family enzyme with unique structure of heterodimer composed of 75 and 15 kDa subunits containing a molybdenum cofactor and [Fe-S] clusters, respectively. The enzyme showed broad substrate specificity toward benzaldehyde derivatives. Furthermore, one-pot conversion of BMAL to BMAL-COOH via BMAL-CHO by the combination of the BMAL-CHO dehydrogenase with P450nov was achieved.
- Hibi, Makoto,Kozono, Iori,Ogawa, Jun,Takeuchi, Michiki
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p. 2390 - 2400
(2020/08/05)
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- Method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by one-pot process
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The invention relates to a method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by a one-pot process. The method is characterized by comprising the following steps: (1) dissolving pyromeconicacid with the concentration of 0.1-5 mol/L in a solvent, adding an alkali, controlling the molar ratio of pyromeconic acid to the alkali to be 1:(0.5-5), adding a formaldehyde aqueous solution with the weight percentage content of 20-50%, controlling the molar ratio of formaldehyde to pyromeconic acid to be (1-3):1, and reacting for 1-24 hours at the temperature of 0-100 DEG C; and (2) directly adding an alkylation reagent into step (1), controlling the molar ratio of the alkylation reagent to pyromeconic acid to be (1-3):1, and reacting at 10-100 DEG C for 1-24 hours. The method has the following advantages: on the basis of ensuring the reaction yield and the product quality, the separation of an intermediate is omitted, the operation steps are reduced, and the production period is shortened; and consumption of solvents and acid-base materials is reduced, and production cost is saved.
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Paragraph 0014; 0017-0031
(2020/09/12)
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- Preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
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The invention relates to a novel synthesis route of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. 3-hydroxy-2-methyl-4H-pyran-4-one used as a raw material undergoes acetyl protection, a brominationreaction, benzyl protection and oxidation reaction to synthesize a dolutegravir intermediate in four steps at a high yield. The above preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid has the advantages of high yield, low cost, environmental protection, easiness operation, and suitableness for realizing industrialization.
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- Synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
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The invention discloses a synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. The synthesis method takes furfuryl alcohol as a starting raw material and four-step reaction including rearrangement, addition, hydroxyl protection and oxidization is carried out; the total mol yield of a synthesis route is greater than 32 percent; the synthesis method has the characteristics of relatively moderate reaction conditions and the like, and the yield and purity of the 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid are remarkably improved; meanwhile, the synthesis method has the advantagesof detailed technological operation steps, specific parameters, controllable conditions and stable technology, and can realize industrial large-batch production.
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Paragraph 0024; 0026; 0028; 0030
(2019/04/02)
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- ANTIVIRAL AGENT
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The present invention provides an integrase inhibitor. The inventors have have found the following compound of formula (I) possessing an integrase inhibitory activity. (wherein, R C and R D taken together with the neighboring carbon atoms form a ring which may be a condensed ring, Y is hydroxy, mercapto or amino; Z is O, S or NH ; R A is a group shown by (wherein, C ring is N-containing aromatic heterocycle) or the like)
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- Orally active iron (III) chelators
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A novel 3-hydroxypyridin-4-one compound of formula I is provided wherein R is hydrogen or a group that is removed by metabolism in vivo to provide the free hydroxy compound, R1 is an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by a hydroxy group or a carboxylic acid ester, sulpho acid ester or a C1-6 alkoxy, C6-aryloxy or C7-10aralkoxy ether thereof, R3 is selected from hydrogen and C1-6alkyl; and R4 is selected from hydrogen, C1-6alkyl and a group as described for R2; characterised in that R2 is selected from groups —CONH—R5??(i) —CH2NHCO—R5??(ii) —SO2NH—R5??(iii) —CH2NHSO2—R5??(iv) —CR6R6OR7??(v) —CONHCOR5??(viii) ?wherein R5 is selected from hydrogen and optionally hydroxy, alkoxy, or aralkoxy substituted C1-13 alkyl, aryl and C71-13 aralkyl, R6 is independently selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl, and R7 is selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl or a pharmaceutically acceptable salt of any such compound with the proviso that when R7 is hydrogen, R6 is not selected from aryl and with the proviso that the compound is not 1-ethyl-2-(1′-hydroxyethyl)-3-hydroxypyridin-4-one.
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- Orally active iron (III) chelators
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A compound of formula I wherein R is hydrogen or a group that is removed by metabolism in vivo to provide the free hydroxy compound, R1is an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by a hydroxy group or a carboxylic acid ester, sulpho acid ester or a C1-6alkoxy, C6-aryloxy or C7-10aralkoxy ether thereof, and R3is selected from hydrogen and C1-6alkyl; characterized in that R2is selected from groups (i) —CONH—R5(ii)—CR6R6OR7(iii) —CONHCOR5and (iv) —CON(CnH2n+1)2 R4is selected from hydrogen, C1-6alkyl and a group as described for R2; R5is selected from hydrogen and optionally hydroxy, alkoxy, aryloxy or aralkoxy substituted C1-13alkyl, aryl and C7-13alkyl R6is independently selected from hydrogen and C1-13alkyl, R7is selected from hydrogen, C1-13alkyl, aryl and C7-13aralkyl or a pharmaceutically acceptable salt of any such compound and CnH2n+1is C1-6alkyl with the proviso that the compound is not one of 1-ethyl-2-(1′-hydroxyethyl)-3-hydroxypyridin-4-one and 1-methyl-2-hydroxymethyl-3-hydroxypyridoin-4-one.
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