Use of RP-TLC to Determine the log P Values of Isomers of Organic Compounds

Stefaniak, Marta; Niestroj, Anna; Klupsch, J.; Śliwiok, J.; Pyka, Alina

doi:10.1365/s10337-005-0569-9

Cited by 13 publications

(9 citation statements)

References 10 publications

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“… a Log P values, taken from Laane et al (17) and Stefaniak et al (30), were calculated from hydrophobic fragmental constants according to Rekker et al (31). …”

Section: Resultsmentioning

confidence: 99%

Microbial Oxidation of Naphthalene to cis‐1,2‐Naphthalene Dihydrodiol Using Naphthalene Dioxygenase in Biphasic Media

McIver

Garikipati

Bankole

et al. 2008

Biotechnology Progress

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The selective oxidation of aryl substrates to chiral cis‐1,2‐dihydrodiols is an industrially important reaction for the production of intermediates that can be used to produce fine chemicals, pharmaceuticals, and many other bioactive natural products. More specifically, the oxidation of naphthalene to produce optically pure (+)‐ cis‐(1 R,2 S)‐1,2‐napthalene dihydrodiol (NDHD) to be used as a chiral synthon for specialty chemicals has gained much interest. Escherichia coli JM109(DE3) pDTG141 expresses naphthalene dioxygenase which catalyzes this reaction. Poor substrate solubility and substrate toxicity are barriers to using the power of these enzymes in large‐scale aqueous whole cell systems. A biphasic reaction system was chosen to overcome these barriers. The optimal biphasic conditions for E. coli JM109(DE3) pDTG141 were determined to be 20% dodecane as the organic solvent containing 40 g/L naphthalene. The productivity of the biotransformation using resting cells was 1.75 g‐diol/g‐cdw/h for the first 6 h with 20% organic phase, which was increased from 0.59 g‐diol/g‐cdw/h for growing cells with 40% organic phase. The biocatalytic activity was retained for at least 12 h. The biocatalyst could be recycled for at least four runs in both suspended and immobilized form. The stability of the 12 h recycle was improved by immobilization in calcium alginate beads. The process has been improved both environmentally and economically by reducing the amount of solvent used and by recycling the biocatalyst.

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“… a Log P values, taken from Laane et al (17) and Stefaniak et al (30), were calculated from hydrophobic fragmental constants according to Rekker et al (31). …”

Section: Resultsmentioning

confidence: 99%

Microbial Oxidation of Naphthalene to cis‐1,2‐Naphthalene Dihydrodiol Using Naphthalene Dioxygenase in Biphasic Media

McIver

Garikipati

Bankole

et al. 2008

Biotechnology Progress

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“…The logP octanol/water values of α-terpineol and oleic acid are 3. 13 .3 and 7, respectively (21). The discrepancy between the polarity of the enhancer-containing oil phase and the aqueous phase was smaller for α-terpineol.…”

Section: Discussionmentioning

confidence: 93%

Permeation Enhancer-Containing Water-In-Oil Nanoemulsions as Carriers for Intravesical Cisplatin Delivery

et al. 2009

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“…Generally, the measurement of experimental log P values has been accomplished using reversed-phase highpressure liquid chromatography [36] or reversed-phase thin-layer chromatography techniques [37]. Moreover, the prediction of log P is often developed using complicated, characterized substructure-based methods and wholemolecule approaches, but one of the possible reasons that these methods have not been successful for complex structures is due to the complexity of quantum mechanical methods and the fact that the solute-solvent interactions are described by the Boltzmann's distribution [36].…”

Section: Log P Prediction -Methods Of Calculations Examples Of Pmentioning

confidence: 99%

The log P Parameter as a Molecular Descriptor in the Computer-aided Drug Design – an Overview

Kujawski¹,

Popielarska²,

Myka³

et al. 2012

CMST

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The computer-aided drug design is an important tool in modern medicinal chemistry. Molecular lipophilicity, usually quantified as log P, is an important molecular characteristic in medicinal chemistry and also in rationalized drug design. The log P coefficient is well-known as one of the principal parameters for the estimation of lipophilicity of chemical compounds and determines their pharmacokinetic properties. This parameter has been measured using known experimental methods, but recently huge progress in determination of log P using computational chemistry methods is observed. The number of methodological publications about lipophilicity predictions has gradually increased over the last ten years, but the number of programs available for an on-line prediction of this important parameter remains limited. This paper presents some of log P prediction methods and very popular programs connected to this topic. The prediction of log P is highly important for the pharmaceutical industry since it limits time-consuming experiments to measure log P required to optimize pharmacodynamic and pharmacokinetic properties of hits and leads. Development of the methods reviewed in this paper concerning log P prediction seems to be a significant tendency in the modern pharmaceutical industry.

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Use of RP-TLC to Determine the log P Values of Isomers of Organic Compounds

Cited by 13 publications

References 10 publications

Microbial Oxidation of Naphthalene to cis‐1,2‐Naphthalene Dihydrodiol Using Naphthalene Dioxygenase in Biphasic Media

Microbial Oxidation of Naphthalene to cis‐1,2‐Naphthalene Dihydrodiol Using Naphthalene Dioxygenase in Biphasic Media

Permeation Enhancer-Containing Water-In-Oil Nanoemulsions as Carriers for Intravesical Cisplatin Delivery

The log P Parameter as a Molecular Descriptor in the Computer-aided Drug Design – an Overview

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