- ALKANE OXIDATION BY MODIFIED HYDROXYLASES
-
This invention relates to modified hydroxylases. The invention further relates to cells expressing such modified hydroxylases and methods of producing hydroxylated alkanes by contacting a suitable substrate with such cells.
- -
-
Paragraph 0323; 0324
(2016/02/16)
-
- Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes
-
Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral methyl carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times.
- Veguillas, Marcos,Solà, Ricard,Shaw, Luke,Maciá, Beatriz
-
p. 1788 - 1794
(2016/04/05)
-
- Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes
-
An efficient catalyst for the enantioselective synthesis of chiral methyl carbinols from aldehydes is presented. The system uses methyltriisopropoxytitanium as a nucleophile and a readily available binaphthyl derivative as a chiral ligand. The enantioselective methylation of both aromatic and aliphatic aldehydes proceeds with good yields and high enantioselectivities under mild conditions.
- Veguillas, Marcos,Solà, Ricard,Fernández-Iba?ez, M. ángeles,Maciá, Beatriz
-
p. 643 - 648
(2016/07/11)
-
- Identification of an ε-keto ester reductase for the efficient synthesis of an (R)-α-lipoic acid precursor
-
Abstract A novel reductase (CpAR2) with unusually high activity toward an ε-keto ester, ethyl 8-chloro-6-oxooctanoate, was isolated from Candida parapsilosis. The asymmetric reduction of ethyl 8-chloro-6-oxooctanoate using Escherichia coli cells coexpressing CpAR2 and glucose dehydrogenase genes gave ethyl (R)-8-chloro-6-hydroxyoctanoate, a key precursor for the synthesis of (R)-α-lipoic acid, in high space-time yield (530 gL-1d-1) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10-L scale. This method provides a greener and more cost-effective method for the industrial production of (R)-α-lipoic acid.
- Zhang, Yu-Jun,Zhang, Wen-Xia,Zheng, Gao-Wei,Xu, Jian-He
-
supporting information
p. 1697 - 1702
(2015/06/02)
-
- Identification of key residues in Debaryomyces hansenii carbonyl reductase for highly productive preparation of (S)-aryl halohydrins
-
Key residues of Debaryomyces hansenii carbonyl reductase in the determination of the reducing activity towards aryl haloketones were identified through combinatorial mutation of conserved residues. This study provides a green and efficient biocatalyst for the synthesis of (S)-aryl halohydrins.
- Xu, Guo-Chao,Shang, Yue-Peng,Yu, Hui-Lei,Xu, Jian-He
-
supporting information
p. 15728 - 15731
(2015/11/02)
-
- A novel P450-based biocatalyst for the selective production of chiral 2-alkanols
-
A P450 monooxygenase from Nocardia farcinica (CYP154A8) catalyses the stereo- and regioselective hydroxylation of n-alkanes, still a challenging task in chemical catalysis. In a biphasic reaction system, the regioselectivity for the C2-position of C7-C9 alkanes was over 90%. The enzyme showed strict S-selectivity for all tested substrates, with enantiomeric excess (ee) of up to 91%. This journal is the Partner Organisations 2014.
- Von Bühler, Clemens J.,Urlacher, Vlada B.
-
supporting information
p. 4089 - 4091
(2014/04/03)
-
- Facile access to chiral alcohols with pharmaceutical relevance using a ketoreductase newly mined from Pichia guilliermondii
-
Chiral secondary alcohols with additional functional groups are frequently required as important and valuable synthons for pharmaceuticals, agricultural and other fine chemicals. With the advantages of environmentally benign reaction conditions, broad reaction scope, and high stereoselectivity, biocatalytic reduction of prochiral ketones offers significant potential in the synthesis of optically active alcohols. A CmCR homologous carbonyl reductase from Pichia guilliermondii NRRL Y-324 was successfully overexpressed. Substrate profile characterization revealed its broad substrate specificity, covering aryl ketones, aliphatic ketones and ketoesters. Furthermore, a variety of ketone substrates were asymmetrically reduced by the purified enzyme with an additionally NADPH regeneration system. The reduction system exhibited excellent enantioselectivity (>99% ee) in the reduction of all the aromatic ketones and ketoesters, except for 2-bromoacetophenone (93.5% ee). Semi-preparative reduction of six ketones was achieved with high enantioselectivity (>99% ee) and isolation yields (>80%) within 12 h. This study provides a useful guidance for further application of this enzyme in the asymmetric synthesis of chiral alcohol enantiomers. Copyright
- Xu, Guochao,Yu, Huilei,Xu, Jianhe
-
p. 349 - 354
(2013/08/22)
-
- Continuous biphasic enzymatic reduction of aliphatic ketones
-
Biphasic reactions offer an attractive alternative for the utilisation of enzymes for conversion of hardly water soluble substrates. Especially, the alcohol dehydrogenase from Lactobacillus brevis was successfully used for the reductive synthesis of enantiopure secondary aliphatic alcohols. With the enzymatic catalyst and the cofactor effectively retained in the reactive aqueous phase, the continuous operation was demonstrated by continuous addition and withdrawal of the non-reactive phase. The four tested substrates 2-heptanone, 2-octanone, 2-nonanone, and 2-decanone showed that the space time yield and turnover numbers (TON) of the enzyme decrease as the availability of the substrate decreases with increasing partition coefficients. Nevertheless, a TONLbADH of up to 478 × 103 could be achieved. Remarkably, the cofactor utilisation turned out to be very high and a TON NADP+ of more than 20 × 103 was easily achievable for both 2-heptanone and 2-octanone by substrate coupled cofactor regeneration with excess of 2-propanol.
- Leuchs, Susanne,Nonnen, Thomas,Dechambre, Dominique,Na'Amnieh, Shukralla,Greiner, Lasse
-
-
- Ionic liquid facilitates biocatalytic conversion of hardly water soluble ketones
-
Ionic liquids represent a promising alternative to conventional cosolvents as biocompatible solubilisers for biocatalysis. This was shown using water miscible ionic liquids to facilitate the stereoselective reduction of hardly water soluble, aliphatic ketones catalysed by the alcohol dehydrogenase from Lactobacillus brevis. Ten ionic liquids were screened for activity and solubility. Improved storage stabilities besides improved enzyme activities, as well as reduced substrate surplus and product inhibitions were found, while applying the most promising AMMOENG 101 in more detailed investigations. Batch reactions with cofactor regeneration via a glucose dehydrogenase showed increased reaction rates; thus underlining the positive influence of AMMOENG 101. For (R)-3-octanol, (R)-2-nonanol, (R)-2-decanol, and (R)-2-octanol space time yields between 250 and 350 mmol L-1 d -1 were achieved.
- Kohlmann, Christina,Robertz, Nora,Leuchs, Susanne,Dogan, Zuebeyde,Luetz, Stephan,Bitzer, Katrin,Na'Amnieh, Shukrallah,Greiner, Lasse
-
experimental part
p. 147 - 153
(2011/10/08)
-
- Utilising hardly-water soluble substrates as a second phase enables the straightforward synthesis of chiral alcohols
-
So far, the alcohol dehydrogenase-catalysed conversion of longer chain aliphatic substrates has been challenging due to their low solubility in aqueous solution. However, by utilising the ketone directly as a second organic phase, the straightforward synthesis of long chain aliphatic chiral alcohols is enabled. The Royal Society of Chemistry.
- Kohlmann, Christina,Robertz, Nora,Leuchs, Susanne,Greiner, Lasse,Na'Amnieh, Shukralla
-
supporting information; experimental part
p. 3093 - 3095
(2011/12/05)
-
- Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid
-
Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99% ee) was observed in the reduction of tert-alkyl ketones. Asymmetric reduction of acyl silanes using chiral anti-pentane-2,4-diol and DNBSA proceeded efficiently in the absence of octanethiol and the corresponding α-silyl alcohols were obtained in high yields with high ees.
- Matsuo, Jun-Ichi,Hattori, Yu,Hashizume, Mio,Ishibashi, Hiroyuki
-
experimental part
p. 6062 - 6069
(2010/10/02)
-
- Preparation of passion fruit-typical 2-alkyl ester enantiomers via lipase-catalyzed kinetic resolution
-
The preparation of ester enantiomers (acetates, butanoates, hexanoates and octanoates) of the secondary alcohols 2-pentanol, 2-heptanol and 2-nonanol via lipase-catalyzed kinetic resolutions was investigated. Conversion rates and stereochemical courses of esterification and hydrolysis reactions catalyzed by commercially available enzyme preparations were followed for the homologous series of these passion fruit-typical 2-alkyl esters by capillary gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)- β-cyclodextrin as chiral stationary phase. An efficient method was developed to prepare the ester enantiomers via lipase-catalyzed esterifications: optically pure (R)-2-alkyl esters (ee > 99.9%) were obtained by esterification of the racemic alcohols with enantioselective Candida antarctica lipase B (immobilized) as catalyst. The subsequent esterification of the unreacted alcohols using lipase from Candida cylindracea yielded the optically enriched (S)-esters (ee > 81.4%). The separation of the products via liquid solid chromatography using a mixture of silica gel and aluminum oxide (basic) resulted in high chemical purities and yields (> 40 mol %).
- Strohalm, Hedwig,Dold, Susanne,Pendzialek, Kathrin,Weiher, Monika,Engel, Karl-Heinz
-
p. 6328 - 6333
(2011/08/09)
-
- Escherichia coli BioH: A highly enantioselective and organic solvent tolerant esterase for kinetic resolution of sec-alcohols
-
Escherichia coli BioH, which is obligatory for biotin synthesis, was found to be an organic solvent tolerant esterase with high enantioselectivity for the kinetic resolution of sec-alcohols using free enzyme powder. With this esterase, a variety of racemic sec-alcohols were efficiently resolved with ee values of up to 99%.
- Wang, Bo,Tang, Xiaoling,Liu, Ji,Yu, Hongwei
-
supporting information; experimental part
p. 6360 - 6364
(2011/01/04)
-
- Enantiocomplementary inverting sec-alkylsulfatase activity in cyano- and thio-bacteria Synechococcus and Paracoccus spp.: selectivity enhancement by medium engineering
-
Whole resting cells of cyano- and thio-bacteria Synechococcus and Paracoccus spp. were shown to possess inverting alkylsulfatase activity for a broad spectrum of sec-alkylsulfate esters, which furnished either (R)- or (S)-sec-alcohols from the correspondi
- Gadler, Petra,Reiter, Tamara C.,Hoelsch, Kathrin,Weuster-Botz, Dirk,Faber, Kurt
-
experimental part
p. 115 - 118
(2009/05/30)
-
- Enantioselective reduction of prochiral ketones employing sprouted Pisum sativa as biocatalyst
-
Sprouted green peas have been used for the first time as biocatalysts for enantioselective reduction of prochiral ketones. The reactions are highly enantioselective to furnish chiral alcohols in good yields. The sprouted peas as biocatalysts are a cheap and easy way for generating some interesting chiral alcohols. This process is efficient and convenient to produce chiral secondary alcohols in water. Georg Thieme Verlag Stuttgart.
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Sreelakshmi, Chittamuru,Rao, Adari Bhaskar
-
experimental part
p. 1881 - 1885
(2010/01/16)
-
- Mechanistic investigation of the Candida albicans CCT 0776 stereoinversion system and application to obtain enantiopure secondary alcohols
-
Phenylethanol deracemization with Candida albicans CCT 0776 whole cells yields the (R)-enantiomer in over 99% enantiomeric excess and 98% yield. The deracemization process involves, in the first step, a fast, highly (S)-selective oxidation (NADP and O2 dependent) and, in the second step, a slower partially (S)-selective reduction (NADH dependent) of the intermediate ketone. The process was extended to other 2-alkanols, 1,2-diols and 1,3-diols and, with the exception of 1,3-diol (unreactive), the enantiomeric excess and yield of the deracemization were about 99% and 62-98%, respectively.
- Mantovani, Simone M.,Angolini, Celio F.F.,Marsaioli, Anita J.
-
experimental part
p. 2635 - 2638
(2010/03/30)
-
- Enzymatic ketone reduction: mapping the substrate profile of a short-chain alcohol dehydrogenase (YMR226c) from Saccharomyces cerevisiae
-
A short-chain alcohol dehydrogenase (YMR226c) from Saccharomyces cerevisiae was cloned and expressed in Escherichia coli, and the encoded protein was purified. The activity and enantioselectivity of this recombinant enzyme were evaluated with a series of ketones. The alcohol dehydrogenase (YMR226c) was found to effectively catalyze the enantioselective reductions of aryl-substituted acetophenones, α-chloroacetophenones, aliphatic ketones, and α- and β-ketoesters. While the enantioselectivity for the reduction of β-ketoesters was moderate, the acetophenone derivatives, aromatic α-ketoesters, some substituted α-chloroacetophenones, and aliphatic ketones were reduced to the corresponding chiral alcohols with excellent enantioselectivity. The enantiopreference of this enzyme generally followed Prelog's rule for the simple ketones. The ester functionality played some role in determining the enzyme's enantiopreference for the reduction of α- and β-ketoesters. The present study serves as a valuable guidance for the future applications of this versatile biocatalyst.
- Yang, Yan,Zhu, Dunming,Piegat, Timothy J.,Hua, Ling
-
p. 1799 - 1803
(2008/02/12)
-
- Synthesis of a fluorous ligand and its application for asymmetric addition of dimethylzinc to aldehydes
-
A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.
- Sokeirik, Yasser S.,Mori, Hiroyuki,Omote, Masaaki,Sato, Kazuyuki,Tarai, Atsushi,Kumadaki, Itsumaro,Ando, Akira
-
p. 1927 - 1929
(2008/02/02)
-
- Stereoselective enzymatic synthesis of chiral alcohols with the use of a carbonyl reductase from Candida magnoliae with anti-prelog enantioselectivity
-
In our effort to search for carbonyl reductases with anti-Prelog enantioselectivity, the activity and enantioselectivity of a carbonyl reductase from Candida magnoliae have been examined with various ketones of diverse structures. This carbonyl reductase catalyzed the reduction of a series of ketones, α-and β-ketoesters, to anti-Prelog configurated alcohols in excellent optical purity. The usefulness of this carbonyl reductase has been demonstrated by synthesis of several chiral alcohol intermediates of pharmaceutical importance.
- Zhu, Dunming,Yang, Yan,Hua, Ling
-
p. 4202 - 4205
(2007/10/03)
-
- Maximise equilibrium conversion in biphasic catalysed reactions: How to obtain reliable data for equilibrium constants?
-
For the prediction and optimisation of the equilibrium conversion in biphasic catalysed reactions, the equilibrium constant of the desired reaction and the partition coefficients of all reactants have to be known. Within this contribution we have examined the alcohol dehydrogenase-catalysed reduction of several linear and aromatic ketones in biphasic reaction media with respect to equilibrium conversion. In this example, the equilibrium constant can be expressed in terms of differences in oxidation-reduction potentials ΔE0. However, for a large variety of organic compounds, these data are quite rare in the literature. To overcome this lack of data, we have utilised methods of computational chemistry to calculate data for the Gibbs free energy ΔGR leading to the equilibrium constants of a homologous series of linear ketones. To obtain comparable data for the reduction of substituted acetophenone derivatives, the Hammett relation leads to the necessary equilibrium constants. Furthermore, we compare the equilibrium conversions of a set of cofactor regeneration methods for the alcohol dehydrogenase-catalysed reductions. These results lead to a time-saving experimental design for the enantioselective reduction of 2-octanone to (R)-2-octanol on a preparative scale utilising biphasic reaction conditions.
- Eckstein,Lembrecht,Schumacher,Eberhard,Spiess,Peters,Roosen,Greiner,Leitner,Kragl
-
p. 1597 - 1604
(2007/10/03)
-
- Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea
-
rac-sec-Alkyl sulfate esters 1a-8a were resolved in low to excellent enantioselectivities with E-values up to > 200 using whole cells of aerobically-grown hyperthermophilic sulfur-metabolizers, such as Sulfolobus solfataricus DSM 1617, Sulfolobus shibatae DSM 5389 and, most notably, Sulfolobus acidocaldarius DSM 639. Significantly enhanced selectivities were obtained using cells grown on sucrose-enriched Brock-medium. The stereochemical course of this biohydrolysis was shown to proceed with strict inversion of configuration, thus the preferred (R)-enantiomers were converted into the corresponding (S)-sec-alcohols to furnish a homochiral product mixture. The Royal Society of Chemistry 2005.
- Wallner, Sabine R.,Nestl, Bettina M.,Faber, Kurt
-
p. 2652 - 2656
(2007/10/03)
-
- Highly enantioselective sec-alkyl sulfatase activity of the marine planctomycete Rhodopirellula baltica shows retention of configuration
-
(Chemical Equation Presented) Hydrolytic enzymes: The marine planctomycete Rhodopirellula baltica DSM 10527 displays high stereo- and enantioselective alkyl sulfatase activity towards (±)-sec-alkyl sulfates with retention of configuration through cleavage of their S-O bond (see scheme; pathway B), whereas inversion of configuration is observed upon cleavage of the C-O bond (pathway A).
- Wallner, Sabine R.,Bauer, Marga,Wuerdemann, Chris,Wecker, Patricia,Gloeckner, Frank O.,Faber, Kurt
-
p. 6381 - 6384
(2007/10/03)
-
- Synthesis of novel axially chiral Rh-NHC complexes derived from BINAM and application in the enantioselective hydrosilylation of methyl ketones
-
Novel axially chiral Rh N-heterocyclic carbene complexes were prepared from axially dissymmetric 1,1′-binaphthalenyl-2,2′-diamine and applied in the Rh-catalyzed enantioselective hydrosilylation of methyl ketones. The corresponding sec-alcohols can be obtained in high yields with good to excellent ee.
- Duan, Wei-Liang,Shi, Min,Rong, Guo-Bin
-
p. 2916 - 2917
(2007/10/03)
-
- Biocatalytic asymmetric hydrogen transfer employing Rhodococcus ruber DSM 44541
-
Nonracemic sec-alcohols of opposite absolute configuration were obtained either by asymmetric reduction of the corresponding ketone using 2-propanol as hydrogen donor or by enantioselective oxidation through kinetic resolution of the rac-alcohol using acetone as hydrogen acceptor employing whole lyophilized cells of Rhodococcus ruber DSM 44541. The microbial oxidation/reduction system exhibits not only excellent stereo- and enantioselectivity but also a broad substrate spectrum. Due to the exceptional tolerance of the biocatalyst toward elevated concentrations of organic materials (solvents, substrates and cosubstrates), the process is highly efficient. The simple preparation of the biocatalyst and its ease of handling turns this system into a versatile tool for organic synthesis.
- Stampfer, Wolfgang,Kosjek, Birgit,Faber, Kurt,Kroutil, Wolfgang
-
p. 402 - 406
(2007/10/03)
-
- Asymmetric reduction of ketones by Geotrichum candidum in the presence of Amberlite Xad, A solid organic solvent
-
Asymmetric reduction of ketones by Geotrichum candidum in the presence of Amberlite XAD, a solid organic solvent, was described. A hydrophobic polymer, XAD, was used as material to control the stereochemical course of microbial reductions. Aliphatic and aromatic ketones were reduced to the corresponding (S)-alcohols in excellent enantiomeric excess (ee) in the presence of XRD while low enantioselectivities were observed in the absence of the polymer.
- Nakamura, Kaoru,Fujii, Mikio,Ida, Yoshiteru
-
p. 3205 - 3211
(2007/10/03)
-
- From Highly Enantioselective Monomeric Catalysts to Highly Enantioselective Polymeric Catalysts: Application of Rigid and Sterically Regular Chiral Binaphthyl Polymers to the Asymmetric Synthesis of Chiral Secondary Alcohols
-
A 1,1′-binaphthyl-based polymeric chiral catalyst with the most general enantioselectivity for the alkylzinc addition to a broad range of aldehydes has been obtained. This polymer can be easily recovered, and the recycled polymer shows the same catalytic properties as the original polymer. A highly enantioselective catalytic diphenylzinc addition to aldehydes has also been achieved by using the chiral binaphthyl monomer and polymer catalysts. Particularly, the excellent enantioselectivity observed for the addition of diphenylzinc to aromatic aldehydes allows the preparation of optically active diaryl carbinols that are synthetically useful but difficult to access by asymmetric catalysis. A novel asymmetric reduction of ketones catalyzed by the mono- and polybinaphthyl zinc complexes has been discovered. Our work on the asymmetric organozinc addition to aldehydes and the asymmetric reduction of ketones catalyzed by the zinc complexes of chiral binaphthyl monomer (R)-12 and polybinaphthyl (R)-43 has not only provided new methods to prepare optically active secondary alcohols but also demonstrated that incorporation of an enantioselective monomeric catalyst into a rigid and sterically regular polymer structure could almost completely preserve the catalytic properties of the monomeric catalyst. This strategy may find general application in converting existing highly enantioselective monomer catalysts into polymer catalysts of similar enantioselectivity provided that the catalytically active species of the monomer catalysts contain only the monomeric units rather than the aggregates of the monomers. By using this strategy, it is possible to overcome the drawbacks associated with the traditional approach to preparing polymeric chiral catalysts where the microenvironments of the catalytic sites in the polymers are often significantly altered from those in the monomeric catalysts due to the flexible and sterically irregular polymer chains.
- Huang, Wei-Sheng,Hu, Qiao-Sheng,Pu, Lin
-
p. 7940 - 7956
(2007/10/03)
-
- Goat Liver Lipase : An Efficient Biocatalyst for Enantioselective Transesterification of Secondary Alcohols using Vinyl Acetate as Acyl Donor
-
Lipase from fresh goat liver has been shown to catalyze enantioselective transesterification of secondary alcohols in hexane using vinyl acetate as acyl source. In most of the cases transesterification takes place with alcohols of R-configuration, whereas in the case of cholesterol only the natural isomer (3S) is acylated with >99% ee.
- Saikia, Anil K.,Bez, Ghanashyam,Bezbarua, Maitreyee S.,Barua, Nabin C.
-
p. 937 - 939
(2007/10/03)
-
- A New NAD-dependent Alcohol Dehydrogenase with Opposite Facial Selectivity useful for Asymmetric Reduction and Cofactor Regeneration
-
A new NAD-dependent alcohol dehydrogenase isolated from a Pseudomonas species catalysed the reduction of many acyclic ketones to optically active alcohols with very high enantioselectivity (90 to >98percent enantiomeric excess); the stereochemical course of the reduction was determined to be the transfer of the pro-(R) hydrogen from NADH to the Si face of the carbonyl group, a process different from that for other known alcohol dehydrogenases.
- Shen, Gwo-Jenn,Wang, Yi-Fong,Bradshaw, Curt,Wong, Chi-Huey
-
p. 677 - 679
(2007/10/02)
-
- ENANTIOSELECTIVE ADDITION OF CHIRALLY MODIFIED METHYLTITANIUM REAGENTS TO AROMATIC ALDEHYDES
-
N-Sulfonylated derivatives of norephedrine are excellent ligands for chirally modified methyltitanium reagents, the latter reacting enantioselectively with aromatic aldehydes (ee ca. 90percent) to form R-cunfigurated carbinols.
- Reetz, M. T.,Kuekenhoehner, T.,Weinig, P.
-
p. 5711 - 5714
(2007/10/02)
-