purifying organic compounds and combinatorial libraries in .NET

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purifying organic compounds and combinatorial libraries
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O CH3 O O OH CH3 O OCH3 H3CO OH O OH O O H3CO CH3 OCH3 OCH3
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Figure 10.1. Structure of elloramycin.
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Table 10.2. Purity and Recovery of Elloramycin by Column Particle Size Particle Size (mm) 10 15 25 Original Purity (%) 96 20 96 20 Final Purity (%) 100 100 97 80 Recovery (%) 93 69 92 83
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loading is increased. A study of the percentage of recovery for pharmaceutical compounds in overloaded column circumstances has been carried out and reported.7 When there is enough separation resolution (e.g., a > 1), the recovery of a desired product nevertheless turns out to be close to 100%. For the puri cation of hydrophobic anthraquinone antibiotics, such as elloramycin (structure in Figure 10.1), the in uence of particle size of the C-18 stationary phase on the puri cation ef ciency has been studied.8 The separation resolution, product purity, and recovery were compared with use of 10 mm and 15 25 mm Nucleosil C-18 column. The results shown in Table 10.2 demonstrate that with small and homogeneous particles used as the stationary phase, the separation resolution and product purity increases dramatically, though the recovery is not signi cantly affected. The C-8 column has been studied for automatic puri cation of reaction mixtures of the amines and aldehydes after the parallel solution-phase reaction.9 The typical column size is 20 50 or 20 75 with 5-mm particle size for 50-mmol materials. The yield of the desired products varied from 20% to 90% with purity >95%.
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reversed-phase semipreparative hplc 10.2.2. Effects of the Mobile Phase
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Combinatorial compounds are highly diverse, although the choice of solid phase is usually limited. The separation of different kinds of the compounds can nevertheless be accomplished by choosing the right mobile phase. The solvent type, ow rate, gradient slope, and chemical modi ers can in uence the separation ef ciency, product recovery, product purity, puri cation speed, and the puri cation cost. Generally, the best solvents for preparative LC mobile phase have the following characteristics:
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Low boiling point for easy and economical sample recovery. Low viscosity for minimum column back pressure and maximum ef ciency. Low levels of nonvolatile impurities. Chemically inertness so as not to cause modi cation of sample and stationary phase. Good solubility properties for sample. Low ammability and toxicity for safety in storage and handling.
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The theoretical studies for condition optimization of the preparative chromatograph has been published.10,11 The theoretical models will not be discussed here, but the results from the studies will simplify the process of method development.They can be used as guidelines, as summarized below:
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The column should be operated at the highest ow rate to maximize the puri cation speed. The loading factor, which is the ratio of the total amount of sample to the column saturation capacity, is higher in gradient elution than in isocratic elution condition. The average concentration of the collected fractions and the puri cation speed are higher in gradient elution than in isocratic. The recovery yield achieved under optimum conditions is the same in gradient and in isocratic elution. The optimum gradient steepness depends mostly on the elution order. It is higher for the puri cation of the less retained component than for that of the more retained one. The volume of the solvents required to wash and to regenerate the column after a batch separation will always be larger in gradient than in isocratic elution.
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purifying organic compounds and combinatorial libraries The gradient retention factor is a more signi cant parameter than the gradient steepness because the former incorporates the retention factor at the initial mobile phase composition. The gradient elution may use less ef cient columns than isocratic elution. The performance in gradient mode is very sensitive to the retention factor of the two components to be separated. Optimizing their retention factors would improve the recovery yield and the purity of the nal products.
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In the methods for the high-throughput puri cation reported in the literature,1 4,12 16 the steep and fast (4 6 minutes) gradient modes were employed for reverse-phase preparative HPLC. For puri cation of small organic molecules, water/acetonitrile or ware/methanol are the most commonly used solvent systems as the mobile phase. Offer 0.05% to 0.1% TFA is added to the mobile phases as a modi er. However, TFA is not a desirable chemical in the nal compound. It may decompose some compounds and is detrimental to the biological screening. Other additives such as formic acid, acetic acid, or propanol may be used instead. The addition of triethylamine or ammonium acetate is to reduce the tailing of basic components in the samples. Using the acidic aqueous mobile phase can make all of the ionized groups protonated and avoid the formation of multiple forms of ions in the column. For separation of the acid labile compounds, the neutral or slightly basic conditions can be used. 10.2.3. Effects of Other Factors
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The scale of a combinatorial library is often on the order of tens of milligrams. In order to work on this scale, a larger diameter column (typically 20-mm internal diameter) is needed. The mobile phase linear velocity (u) is expressed as u= where F = ow rate e0 = column porosity d = column diameter 4F , pe 0 d 2 (10.1)
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