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ECSOC-17

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 May 2014) | Viewed by 32759

Special Issue Editor

Departamento de Química Orgánica, Universidad de Santiago de Compostela, Facultad de Ciencias-Campus de Lugo, Alfonso X el Sabio, 27002 Lugo, Spain
Interests: synthesis of compounds with biologic activity; synthesis of compounds with interest for agro-food field; solation, structural determination and synthesis of natural products; microwave organic reactions enhancement
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Special Issue Information

For more information on The 17th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-17), please go to: http://www.sciforum.net/conf/ecsoc-17

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Published Papers (5 papers)

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Research

4174 KiB  
Article
Calculating Distortions of Short DNA Duplexes with Base Pairing Between an Oxidatively Damaged Guanine and a Guanine
by Masayo Suzuki, Katsuhito Kino, Masayuki Morikawa, Takanobu Kobayashi and Hiroshi Miyazawa
Molecules 2014, 19(8), 11030-11044; https://doi.org/10.3390/molecules190811030 - 28 Jul 2014
Cited by 6 | Viewed by 6046
Abstract
DNA is constantly being oxidized, and oxidized DNA is prone to mutation; moreover, guanine is highly sensitive to several oxidative stressors. Several oxidatively damaged forms of guanine—including 2,2,4-triamino-5(2H)-oxazolone (Oz), iminoallantoin (Ia), and spiroiminodihydantoin (Sp)—can be paired with guanine, and cause G:C-C:G [...] Read more.
DNA is constantly being oxidized, and oxidized DNA is prone to mutation; moreover, guanine is highly sensitive to several oxidative stressors. Several oxidatively damaged forms of guanine—including 2,2,4-triamino-5(2H)-oxazolone (Oz), iminoallantoin (Ia), and spiroiminodihydantoin (Sp)—can be paired with guanine, and cause G:C-C:G transversions. Previous findings indicate that guanine is incorporated more efficiently opposite Oz than opposite Ia or Sp, and that these differences in efficiency cannot be explained by differences in the stabilities of G:Oz, G:Ia, and G:Sp base pairs calculated ab initio. Here, to explain previous experimental result, we used a 3-base-pair model DNA duplex to calculate the difference in the stability and the distortion of DNA containing a G:Oz, G:Ia, or G:Sp base pair. We found that the stability of the structure containing 5ꞌ and 3ꞌ base pairs adjacent to G:Oz was more stable than that containing the respective base pairs adjacent to G:Ia or G:Sp. Moreover, the distortion of the structure in the DNA model duplex that contained a G:Oz was smaller than that containing a G:Ia or G:Sp. Therefore, our discussion can explain the previous results involving translesion synthesis past an oxidatively damaged guanine. Full article
(This article belongs to the Special Issue ECSOC-17)
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2294 KiB  
Article
Batch and Continuous Flow Preparation of Hantzsch 1,4-Dihydropyridines under Microwave Heating and Simultaneous Real-time Monitoring by Raman Spectroscopy. An Exploratory Study
by Sylvain Christiaens, Xavier Vantyghem, Marilena Radoiu and Jean Jacques Vanden Eynde
Molecules 2014, 19(7), 9986-9998; https://doi.org/10.3390/molecules19079986 - 09 Jul 2014
Cited by 15 | Viewed by 6902
Abstract
Dialkyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates have been prepared in a batch mode under conventional heating as well as under continuous flow conditions in the Miniflow 200SS, Sairem’s microwave-assisted batch and continuous flow equipment. Real-time monitoring of the reactions by Raman spectroscopy enabled to compare both heating [...] Read more.
Dialkyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates have been prepared in a batch mode under conventional heating as well as under continuous flow conditions in the Miniflow 200SS, Sairem’s microwave-assisted batch and continuous flow equipment. Real-time monitoring of the reactions by Raman spectroscopy enabled to compare both heating modes and to determine (optimized) reaction times. Full article
(This article belongs to the Special Issue ECSOC-17)
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501 KiB  
Article
Formation of a Flavin-Linked Peptide
by Masayuki Morikawa, Katsuhito Kino, Takeshi Senda, Masayo Suzuki, Takanobu Kobayashi and Hiroshi Miyazawa
Molecules 2014, 19(7), 9552-9561; https://doi.org/10.3390/molecules19079552 - 04 Jul 2014
Cited by 3 | Viewed by 5803
Abstract
In a previous study, we showed that formylmethylflavin (FMF) can bind to cysteine. In this study, FMF was reacted with native peptides (CG and CKLVFF) containing an N-terminal cysteine. The formation of flavin-CG and flavin-CKLVFF was confirmed using HPLC and ESI-MS. Storage of [...] Read more.
In a previous study, we showed that formylmethylflavin (FMF) can bind to cysteine. In this study, FMF was reacted with native peptides (CG and CKLVFF) containing an N-terminal cysteine. The formation of flavin-CG and flavin-CKLVFF was confirmed using HPLC and ESI-MS. Storage of flavin-CKLVFF in DMSO at −30 °C for 7 days resulted in no detectable deposition. In contrast, flavin-CKLVFF formed deposits when stored in water at −30 °C for 1 day, but no deposit was observed in the aqueous solution of flavin-CKLVFF after 7 days storage in the presence of 0.1% Triton X-100. Full article
(This article belongs to the Special Issue ECSOC-17)
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419 KiB  
Article
New Potentially Active Pyrazinamide Derivatives Synthesized Under Microwave Conditions
by Ondrej Jandourek, Martin Dolezal, Jiri Kunes, Vladimir Kubicek, Pavla Paterova, Matus Pesko, Vladimir Buchta, Katarina Kralova and Jan Zitko
Molecules 2014, 19(7), 9318-9338; https://doi.org/10.3390/molecules19079318 - 03 Jul 2014
Cited by 6 | Viewed by 7464
Abstract
A series of 18 N-alkyl substituted 3-aminopyrazine-2-carboxamides was prepared in this work according to previously experimentally set and proven conditions using microwave assisted synthesis methodology. This approach for the aminodehalogenation reaction was chosen due to higher yields and shorter reaction times compared [...] Read more.
A series of 18 N-alkyl substituted 3-aminopyrazine-2-carboxamides was prepared in this work according to previously experimentally set and proven conditions using microwave assisted synthesis methodology. This approach for the aminodehalogenation reaction was chosen due to higher yields and shorter reaction times compared to organic reactions with conventional heating. Antimycobacterial, antibacterial, antifungal and photosynthetic electron transport (PET) inhibiting in vitro activities of these compounds were investigated. Experiments for the determination of lipophilicity were also performed. Only a small number of substances with alicyclic side chain showed activity against fungi which was the same or higher than standards and the biological efficacy of the compounds increased with rising lipophilicity. Nine pyrazinamide derivatives also inhibited PET in spinach chloroplasts and the IC50 values of these compounds varied in the range from 14.3 to 1590.0 μmol/L. The inhibitory activity was connected not only with the lipophilicity, but also with the presence of secondary amine fragment bounded to the pyrazine ring. Structure-activity relationships are discussed as well. Full article
(This article belongs to the Special Issue ECSOC-17)
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333 KiB  
Article
Microwave-Assisted Kinetic Resolution of Homochiral (Z)-Cyclooct-5-ene-1,2-diol and (Z)-2-Acetoxycyclooct-4-enyl Acetate Using Lipases
by Hervé Rouillard, Emmanuel Deau, Lisianne Domon, Jean-René Chérouvrier, Marianne Graber and Valérie Thiéry
Molecules 2014, 19(7), 9215-9227; https://doi.org/10.3390/molecules19079215 - 02 Jul 2014
Cited by 5 | Viewed by 5871
Abstract
Over the last decade, the use of biocatalysts has become an attractive alternative to conventional chemical methods, especially for organic synthesis, due to their unusual properties. Among these enzymes, lipases are the most widely used, because they are cheap, easily available, cofactor-free, and [...] Read more.
Over the last decade, the use of biocatalysts has become an attractive alternative to conventional chemical methods, especially for organic synthesis, due to their unusual properties. Among these enzymes, lipases are the most widely used, because they are cheap, easily available, cofactor-free, and have broad substrate specificity. Combined to microwave heating in non-aqueous medium, recent results suggest that irradiation may influence the enzyme activity. This Communication reports the benefits of lipases and the microwave irradiation on the kinetic resolution of racemic homochiral (Z)-cyclooct-5-ene-1,2-diol and (Z)-2-acetoxycyclooct-4-enyl acetate. In order to best achieve the kinetic resolution, different parameters were studied including the type of lipase, the temperature, the impact of microwave power compared to conventional heating. Optimization of the reaction parameters lead to the obtainment of highly enriched or enantiopure diols and diesters in a clean, efficient and safe way. Full article
(This article belongs to the Special Issue ECSOC-17)
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