- Large-scale synthesis of the glucosylceramide synthase inhibitor N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
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A synthetic route for the preparation of glucosylceramide synthase inhibitor N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin methanesulfonic acid salt (AMP-DNM) has been developed. Herein we report the development and optimization of this synthetic route from its initial version in an academic research laboratory at milligram-scale to the final optimized route that was implemented in a cGMP miniplant on kilogram-scale. The definitive route starts with the separate synthesis of building blocks 2,3,4,6-tetra-O- benzyl-1-deoxynojirimycin and 5-(adamantan-1-ylmethoxy)-pentanal. The aldehyde was synthesized from 1,5-pentanediol in five steps and 45% overall yield. Protected 1-deoxynojirimycin was prepared by a successive hemiacetal reduction/Swern oxidation/double reductive amination sequence of 2,3,4,5-tetra-O-benzyl-D-glucopyranose in 52% overall yield. Reductive amination of the two building blocks produced the benzylprotected penultimate that was isolated as its crystalline (+)DTTA salt in 68% yield. Hydrogenolysis of the penultimate and crystallization of the end product as its methanesulfonic acid salt produced AMP-DNM in 76% yield with a purity of >99.5%. The described route enables the production of multikilogram amounts of inhibitor AMP-DNM as a stable crystalline solid with high purity under cGMP control.
- Wennekes, Tom,Lang, Bemhard,Leeman, Michel,Van Der Marel, Gijsbert A.,Smits, Elly,Weber, Matthias,Van Wiltenburg, Jim,Wolberg, Michael,Aerts, Johannes M.F.G.,Overkleeft, Herman S.
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- Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors
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We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (
- Ahuja-Casarín, Ana I.,Merino-Montiel, Penélope,Vega-Baez, José Luis,Montiel-Smith, Sara,Fernandes, Miguel X.,Lagunes, Irene,Maya, Inés,Padrón, José M.,López, óscar,Fernández-Bola?os, José G.
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p. 138 - 146
(2020/11/27)
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- Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors
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To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyldeoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NBDNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1- (4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5- methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α- glucosidase. Additionally, an arene-arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene-arene interaction resulted in a low binding energy (-5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type II diabetes.
- Zeng, Fanxin,Yin, Zhongping,Chen, Jiguang,Nie, Xuliang,Lin, Ping,Lu, Tao,Wang, Meng,Peng, Dayong
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- Structure–Activity Studies of N-Butyl-1-deoxynojirimycin (NB-DNJ) Analogues: Discovery of Potent and Selective Aminocyclopentitol Inhibitors of GBA1 and GBA2
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Analogues of N-butyl-1-deoxynojirimycin (NB-DNJ) were prepared and assayed for inhibition of ceramide-specific glucosyltransferase (CGT), non-lysosomal β-glucosidase 2 (GBA2) and the lysosomal β-glucosidase 1 (GBA1). Compounds 5 a–6 f, which carry sterically demanding nitrogen substituents, and compound 13, devoid of the C3 and C5 hydroxy groups present in DNJ/NB-DGJ (N-butyldeoxygalactojirimycin) showed no inhibitory activity for CGT or GBA2. Inversion of stereochemistry at C4 of N-(n-butyl)- and N-(n-nonyl)-DGJ (compounds 24) also led to a loss of activity in these assays. The aminocyclopentitols N-(n-butyl)- (35 a), N-(n-nonyl)-4-amino-5-(hydroxymethyl)cyclopentane- (35 b), and N-(1-(pentyloxy)methyl)adamantan-1-yl)-1,2,3-triol (35 f), were found to be selective inhibitors of GBA1 and GBA2 that did not inhibit CGT (>1 mm), with the exception of 35 f, which inhibited CGT with an IC50 value of 1 mm. The N-butyl analogue 35 a was 100-fold selective for inhibiting GBA1 over GBA2 (Ki values of 32 nm and 3.3 μm for GBA1 and GBA2, respectively). The N-nonyl analogue 35 b displayed a Ki value of ?14 nm for GBA1 inhibition and a Ki of 43 nm for GBA2. The N-(1-(pentyloxy)methyl)adamantan-1-yl) derivative 35 f had Ki values of ≈16 and 14 nm for GBA1 and GBA2, respectively. The related N-bis-substituted aminocyclopentitols were found to be significantly less potent inhibitors than their mono-substituted analogues. The aminocyclopentitol scaffold should hold promise for further inhibitor development.
- Gu, Xingxian,Gupta, Vijayalaxmi,Yang, Yan,Zhu, Jin-Yi,Carlson, Erick J.,Kingsley, Carolyn,Tash, Joseph S.,Sch?nbrunn, Ernst,Hawkinson, Jon,Georg, Gunda I.
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p. 1977 - 1984
(2017/11/30)
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- Concise synthesis of 1-epi-castanospermine
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1-epi-Castanospermine (5) was synthesized from readily available 2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin (11) in 9 steps and 21% overall yield, with selective debenzylation, Barbier reaction and reductive amination as the main reaction steps.
- Cheng, Bin,Li, Yi-Xian,Jia, Yue-Mei,Yu, Chu-Yi
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supporting information
p. 1688 - 1692
(2017/07/27)
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- A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase
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Human nonlysosomal glucosylceramidase (GBA2) is one of several enzymes that controls levels of glycolipids and whose activity is linked to several human disease states. There is a major need to design or discover selective GBA2 inhibitors both as chemical tools and as potential therapeutic agents. Here, we describe the development of a fluorescence polarization activity-based protein profiling (FluoPol-ABPP) assay for the rapid identification, from a 350+ library of iminosugars, of GBA2 inhibitors. A focused library is generated based on leads from the FluoPol-ABPP screen and assessed on GBA2 selectivity offset against the other glucosylceramide metabolizing enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA), and the cytosolic retaining β-glucosidase, GBA3. Our work, yielding potent and selective GBA2 inhibitors, also provides a roadmap for the development of high-throughput assays for identifying retaining glycosidase inhibitors by FluoPol-ABPP on cell extracts containing recombinant, overexpressed glycosidase as the easily accessible enzyme source.
- Lahav, Dani?l,Liu, Bing,Van Den Berg, Richard J.B.H.N.,Van Den Nieuwendijk, Adrianus M. C. H.,Wennekes, Tom,Ghisaidoobe, Amar T.,Breen, Imogen,Ferraz, Maria J.,Kuo, Chi-Lin,Wu, Liang,Geurink, Paul P.,Ovaa, Huib,Van Der Marel, Gijsbert A.,Van Der Stelt, Mario,Boot, Rolf G.,Davies, Gideon J.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.
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supporting information
p. 14192 - 14197
(2017/10/17)
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- Selenoureido-iminosugars: A new family of multitarget drugs
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Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for tackling simultaneously the Gaucher disease (by selective inhibition of β-glucosidase, Ki= 1.6–5.5 μM, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, Kiup to 5.8 μM). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2(Kcat/Kuncatup to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)2and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders.
- Olsen, Jacob Ingemar,Plata, Gabriela B.,Padrón, José M.,López, óscar,Bols, Mikael,Fernández-Bola?os, José G.
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p. 155 - 160
(2016/08/01)
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- High sugar composition for treatment and method
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The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of hyperglycemia may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of insulin resistance, diabetes mellitus, diabetes insipidus, type 1 diabetes, type 2 diabetes, microvascular complications, macrovascular complications, lipid disorders, prediabetes, obesity, arrhythmia, myocardial infarction, stroke, neuropathy, renal complications, hypertriglyceridemia, cardiovascular complications, and post prandial hyperglycemia.
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Paragraph 0095-0098
(2017/03/25)
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- Chemical synthesis of 1-deoxy-L-fructose and L-sorbose through carbonyl translocation
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Two rare sugars - 1-deoxy-L-fructose and L-sorbose - were synthesized from inexpensive starting materials by a carbonyl translocation method developed in our laboratory. Reduction of a known starting compound gave a 1,5-diol derivative. Selective protecti
- Wu, Hsin-Pei,Hsu, Nai-Yun,Lu, Tai-Ni,Chang, Che-Chien
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p. 378 - 382
(2015/03/05)
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- Compositions and methods for the treatment of hyperglycemia
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The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of hyperglycemia may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of insulin resistance, diabetes mellitus, diabetes insipidus, type 1 diabetes, type 2 diabetes, microvascular complications, macrovascular complications, lipid disorders, prediabetes, obesity, arrhythmia, myocardial infarction, stroke, neuropathy, renal complications, hypertriglyceridemia, cardiovascular complications, and post prandial hyperglycemia.
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Page/Page column 25; 26
(2015/10/28)
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- Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate
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The total synthesis of (+)-valienamine and (-)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.
- Li, Qing Ri,Kim, Seung In,Park, Sook Jin,Yang, Hye Ran,Baek, A Reum,Kim, In Su,Jung, Young Hoon
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p. 10384 - 10390
(2013/11/19)
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- Iminosugar analogues of phosphatidyl inositol as potential inhibitors of protein kinase B (Akt)
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A small virtual library of iminosugar derivatives was evaluated by docking experiments carried out by sampling a protein region corresponding to the phosphoinositide binding site of the PH domain of Akt. Four compounds were selected and efficiently synthesised from a common precursor. All compounds were subjected to preliminary biological evaluation on purified enzyme, and - among them - compound 9 exhibited the best inhibitory activity. A small virtual library of iminosugar-based Akt inhibitors have been designed and evaluated by using docking calculations. Selected compounds have been conveniently synthesised, and preliminary biological evaluation identified compound 9 as a possible lead compound for further development of iminosugar-based Akt inhibitors. Copyright
- Orsato, Alexandre,Barbagallo, Emanuela,Costa, Barbara,Olivieri, Sandro,De Gioia, Luca,Nicotra, Francesco,La Ferla, Barbara
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experimental part
p. 5012 - 5019
(2011/11/14)
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- Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol
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A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright
- Zhang, Zhen-Xing,Wu, Baolin,Wang, Bin,Li, Tie-Hai,Zhang, Peng-Fei,Guo, Li-Na,Wang, Wen-Jun,Zhao, Wei,Wang, Peng George
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supporting information; experimental part
p. 3802 - 3804
(2011/08/09)
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- Stereocontrolled formation of protected aminodeoxyalditols from simple carbohydrate precursors by debenzylating cycloetherification
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A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ringforming reaction sequence from glucose, mannose, and galactose derivatives
- Jiang, Yuhua,Fang, Zhijie,Zheng, Qiangang,Jia, Hailang,Cheng, Jie,Zheng, Baohui
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experimental part
p. 2756 - 2760
(2010/01/21)
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- Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
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Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either d-glucose or l-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
- Cumpstey, Ian,Gehrke, Sebastian,Erfan, Sayeh,Cribiu, Riccardo
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p. 1675 - 1692
(2008/12/21)
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- Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man
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(Chemical Equation Presented) In this article, we present a straightforward synthesis of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives. The used synthetic routes are flexible and can be used to create a wide variety of lipophilic mo
- Wennekes, Tom,Van Den Berg, Richard J. B. H. N.,Donker, Wilma,Van Der Marel, Gijsbert A.,Strijland, Anneke,Aerts, Johannes M. F. G.,Overkleeft, Herman S.
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p. 1088 - 1097
(2007/10/03)
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- Cis-stereoselective SmI2-promoted reductive coupling of keto-nitrones: First synthesis of 1-epitrehazolamine
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An expeditious synthesis of 1-epitrehazolamine is presented from readily available 2,3,4,6-tetra-O-benzyl-D-glucose. The key step involves a samarium diiodide-promoted reductive cyclization of a masked keto-nitrone to form a fivemembered ring aminocyclito
- Masson, Geraldine,Philouze, Christian,Py, Sandrine
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p. 2067 - 2069
(2007/10/03)
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- Reductive ring-opening reaction of 1,2-O-benzylidene and 1,2-O-p-methoxybenzylidene-α-D-glucopyranose using diisobutyl aluminum hydride
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Regioselectivity in the reductive ring-opening reaction of 3,4,6-tri-O-benzyl-1,2-O-benzylidene and 3,4,6-tri-O-benzyl-1,2-O-p- methoxybenzylidene-α-D-glucopyranose using diisobutyl aluminum hydride (DIBAH) was examined. The ratio of the 1-O- and 2-O-p-me
- Suzuki, Katsuhiko,Nonaka, Hisato,Yamaura, Masanori
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p. 253 - 259
(2007/10/03)
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- Nitrogen inversion as a diastereomeric relay in azasugar synthesis: The first synthesis of adenophorine
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A temperature-dependent relay of chirality is based on the inversion of the nitrogen lone pair in cyclic azasugars. Elimination from the conformation preferred at a given temperature leads to a cyclic imine, and in a subsequent nucleophilic attack the ste
- Maughan, Michael A. T.,Davies, Ieuan G.,Claridge, Timothy D. W.,Courtney, Steve,Hay, Phil,Davis, Benjamin G.
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p. 3788 - 3792
(2007/10/03)
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- Cyclization dichotomy of D-xylo-hex-5-ulosonamides and synthesis of piperidine analogs of aldohexoses and aldohexono-1,5-lactones
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The preparation of 2,3,4,6-tetra-O-benzyl-S-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino-2,3,4,6-tetra-O-benzyl-S-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra
- Kovarikova, Radka,Ledvina, Miroslav,Saman, David
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p. 673 - 684
(2007/10/03)
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- Synthesis of 1-deoxynojirimycin and N-butyl-1-deoxynojirimycin
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1-Deoxynojirimycin (1) is a natural alkaloid with several biological activities; the analog N-butyl-1-deoxynojirimycin (4), for example has shown potent anti HIV-1 and HIV-2 activity without cytotoxicity. As part of a program to synthesize compounds with biological activity against retroviruses, we developed an efficient route for the preparation of 1 and 4 employing as raw material glucose and others inexpensive reagents.
- Matos, Carlos R. R.,Lopes, Rosangela S. C.,Lopes, Claudio C.
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p. 571 - 573
(2007/10/03)
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- A Highly Efficient Pinacol Coupling Approach to Trehazolamine Starting from D-Glucose
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A short and very efficient synthesis of trehazolamine (3), the aglycon of the potent trehalase inhibitor trehazolin (2), has been achieved starting from D-glucose. The key transformation in this approach is a high-yielding two-step, one-pot sequence consisting of a Swern oxidation of a 1,5-diol followed by a reductive carbocyclization of the resultant 1,5-dicarbonyl compound promoted by samarium diiodide. The overall yield of 3 is 39% over nine steps from 2,3,4,6-tetra-O-benzyl-D-glucose (5). An even shorter synthesis of 30, a diastereoisomeric analogue of 3, is also described starting from 5. The key transformation in this second route is a highly stereoselective ketone oxime ether reductive carbocyclization promoted also by samarium diiodide. The overall yield of 30 is 57% over four steps from 5.
- De Gracia, Isabel Storch,Dietrich, Hansjoerg,Bobo, Sofia,Chiara, Jose Luis
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p. 5883 - 5889
(2007/10/03)
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- Diastereoselectivity of the cyclization of hexos-5-uloses by Sm2-mediated pinacol coupling
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2,3,4,6-Tera-O-benzyl-hexos-5-uloses derived from D-glucose, D- mannose and D-galactose have been cyclized to cis-diols by a one pot Swerm oxidation/SmI2-mediated pinacol coupling procedure. The effect of the substituent orientation on the diastereoselectivity of the coupling step is examined.
- Adinolfi, Matteo,Barone, Gaspare,Iadonisi, Alfonso,Mangoni, Lorenzo
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p. 2021 - 2024
(2007/10/03)
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- SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-L-IDOPYRANOSE
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A synthesis of 2,3,4,6-tetra-O-benzyl-L-idopyranose (15) is described, based on L-sorbose as the starting material.By a succession of well known, high-yielding procedures, the ketose was converted into a 2:1 mixture of 1,3,4,5-tetra-O-benzyl-2-O-(tert-but
- Helleur, Robert,Rao, Vanga S.,Perlin, Arthur S.
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- C-Nucleoside Studies. Part 13. A New Synthesis of 2,3,5-Tri-O-benzyl-α(and β)-D-ribofuranosylethyne Involving Benzyloxy Participation, and a Synthesis of α-Showdomycin
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2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60 deg C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group.The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-benzyl-1-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its O-5 oxyanion.Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α (and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose.A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer showdomycin, from (20) is described.
- Aslani-Shotorbani, Gaffar,Buchanan, J. Grant,Edgar, Alan R.,Shanks, Colin T.,Williams, Gavin C.
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p. 2267 - 2272
(2007/10/02)
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- Regioselective eliminations in reactions of carbohydrate derivatives with superoxide, or with borohydride in 2-propanol
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The reaction between 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol (2) and potassium superoxide resulted in the loss of H-4 and the 5-mesyloxy (as well as 1-mesyloxy) substituent, and an almost quantitative conversion into enol ether 4, i.e., 1,3,4,5-tetra-O-benzyl-3-dehydro-2-deoxy-L-threo-hex-2-enitol.When the reaction was performed with 8, in which the 1-O-mesyl group (of 2) is replaced by O-(methoxy)trityl, the outcome was wholly different: an olefin was formed through the removal of a primary (H-6) rather than a secondary (H-4) proton, and nucleophilic displacement also took place.Results similar to those for 8 were obtained with the 2-epimer of 2, i.e., 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-mannitol (12).It is suggested that selective displacement of the 1-O-mesyl group of 2 by superoxide generates a 1-peroxy anion (6) that abstracts H-4 intramolecularly, promoting concomitant loss of the 5-mesyloxy group.The transition state for proton abstraction within anion 6 appears to be more stable than that of the corresponding anion in the manno series, accounting for the different reaction routes for 2 and 12.Elimination occured also in the reduction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with sodium borohydride in 2-propanol, en route to 2, affording 2,4,6-tri-O-benzyl-2-dehydro-3-deoxy-D-threo-hex-2-enitol (21).The (1)H nmr spectra of alditol derivatives 2, 8, and 12 show that these molecules depart substantially from extended zigzag conformations, in contrast to configurationally related peracetylated acyclic derivatives.
- Rao, Vanga S.,Perlin, Arthur S.
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p. 333 - 338
(2007/10/02)
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