Royal Society of Chemistry

Synthesis of chitin and chitosan stereoisomers by thermostable alpha-glucan phosphorylase-catalyzed enzymatic polymerization of alpha-D-glucosamine 1-phosphate

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00167F, PaperJun-ichi Kadokawa, Riko Shimohigoshi, Kento Yamashita, Kazuya Yamamoto
The relationship between two aminopolysaccharide stereoisomers, namely alpha-(1,4)- and beta-(1,4)-linked (N-acetyl)-D-glucosamine polymers, is of significant interest within the field of polysaccharide science, as they correspond to amino analogs of the...
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Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to [small alpha],[small beta]-unsaturated acyl phosphonates for the synthesis of 3,3'-disubstituted oxindoles with chiral squaramides

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00317B, CommunicationLin Chen, Yong You, Ming-Liang Zhang, Jian-Qiang Zhao, Jian Zuo, Xiao-Mei Zhang, Weicheng Yuan, Xiao-Ying Xu
A highly enantioselective Michael addition of 3-monosubstituted oxindoles to [small alpha],[small beta]-unsaturated acyl phosphonates with chiral squaramides as catalysts was investigated for the first time. A wide range of 3,3'-disubstituted oxindole adducts...
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PtI2-Catalyzed Cyclization of 3-Acyloxy-1,5-enynes with the Elimination of HOAc and a benzyl Shift: Synthesis of Unsymmetrical m-Terphenyls

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02336F, Paperlingyan liu, Jing Li, xiufang xu, Kaimeng Huang, Hongkai Wang, Junying Wang, Xiaona Ke, Chenchen Zhou
A novel cyclization of 3-acyloxy-1,5-enynes was developed in the presence of PtI2 for the synthesis of substituted unsymmetrical m-terphenyls in good to excellent yields. Two unique steps were involved in...
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Synthesis of novel tryptamine-based macrocycles using a Ugi 4-CR/microwave assisted click-cycloaddition reaction protocol

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00067J, CommunicationLuis D. Miranda, Lizbeth Chavez-Acevedo
A practical synthesis of novel tryptamine-based macrocycles using a Ugi 4-CR/click-cycloaddition sequential reaction protocol is descrived. The main features of the macrocyclic scaffolds are a peptoid moiety, a 1,3-substituted indole...
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Palladium-Catalyzed Oxidative C-H/C-H Cross-Coupling of 1-Substituted 1,2,3-Triazoles with Furans and Thiophenes

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00102A, PaperXin Yu, Wei Liu, Suping Shi, Chunxiang Kuang, Zhendong Huang
Palladium-catalyzed heteroarylation of 1-substituted 1,2,3-triazoles with furans and thiophens has been developed, in the presence of pyridine and Ag2CO3. The procedure is suitable for the regioselective preparation of 1,5-disubstituted 1,2,3-triazoles...
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Chirality Extension of Oxazine Building Block En Route to Total Syntheses of (+)-Hyacinthacine A2 and Sphingofungin B

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00251F, PaperSeok-Hwi Park, Xiangdan Jin, Jong-Cheol Kang, Changyoung Jung, Seong-Soo Kim, Sung-Soo Kim, Kee-Young Lee, Won Hun Ham
Concise and stereocontrolled syntheses of (+)-hyacinthacine A2 and sphingofungin B were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include palladium(0)-catalyzed intramolecular oxazine formation and diastereoselective nucleophilic addition...
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Peptide-DNA conjugates as tailored bivalent binders of the oncoprotein c-Jun

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00318K, PaperElena Pazos, Cecilia Portela, Cristina Penas, M. Eugenio Vazquez, Jose Luis Mascarenas
We describe a ds-oligonucleotide-peptide conjugate that is able to efficiently dismount preformed DNA complexes of the bZIP regions of oncoproteins c-Fos and c-Jun (AP-1), and therefore might be useful as...
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Near-infrared emission of dibenzoxanthenium and its application in the design of nitric oxide probes

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00042D, PaperWu Liu, Chen Fan, Ru Sun, Yu-Jie Xu, Jian-Feng Ge
Two dibenzoxanthenium derivatives bearing a 3,4-diaminophenyl group, compounds 1a and 1b, have been prepared and evaluated as near-infrared probes for the detection of nitric oxide. Compound 1a gave a 3-fold...
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Synthesis of 2,4-diarylsubstituted-pyridines through Ru-catalyzed four component reaction

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00162E, CommunicationGuo-Jun Deng, Yang Bai, Lichang Tang, Huawen Huang
A ruthenium-catalyzed one-pot synthesis of 2,4-diarylsubstituted pyridines from acetophenones, ammonium acetate and DMF under oxygen atmosphere is described. The carbon atom situated at C6 of the pyridine ring comes from...
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Chemical Synthesis of Outer Core Oligosaccharide of Escherichia coli R3 and Immunological Evaluation

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00177C, PaperWenjing Shang, Zhongying Xiao, Zaikuan Yu, Na Wei, Guohui Zhao, Qing Zhang, Mohui Wei, Xuan Wang, Peng George Wang, Tiehai Li
Lipopolysaccharides (LPS), major virulence determinants in Gram?negative bacteria, are responsible for many pathophysiological responses and can elicit strong immune responses. In order to better understand the role of LPS in...
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Facile synthesis of spirooxindole-pyrazolines and spirobenzofuranone-pyrazolines and their fungicidal activity

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00258C, PaperChangjiang Yang, Juanjuan Li, Rong Zhou, Xiangyu Chen, Yunpeng Gao, Zhengjie He
Novel spirooxindole-pyrazolines and spirobenzofuranone-pyrazolines have been synthesized in good to excellent yields via the annulation reactions of the corresponding 3-alkylideneoxindoles and 3-alkylidenebenzofuranones with Huisgen zwitterions. The preliminary bioassay has demonstrated...
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An Efficient Access to Enantiopure 1,3-disubstituted Isoindolines from Selective Catalytic Fragmentation of Original Desymmetrized Rigid Overbred Template

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00229J, PaperGanesh Pandey, Rajesh Varkhedkar, Divya Tiwari
An efficient and scalable synthesis of various enantiopure 1,3- disubstituted isoindolines are reported. The base catalyzed nucleophilic fragmentation of a rigid overbred template is established with various substrates to afford...
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Concise Synthetic Approach to Brazilin via Pd-Catalyzed Allylic Arylation

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00216H, PaperYoungeun Jung, Ikyon Kim
A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed...
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Regioselective solid-phase synthesis of N-mono-hydroxylated and N-mono-methylated acylpolyamine spider toxins using an 2-(ortho-nitrophenyl)ethanal-modified resin

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00108K, PaperStefan Bienz, Denise Pauli
A recently introduced new SPS resin, possessing an 2-(ortho-nitrophenyl)ethanal linker, was used for the regioselective on-resin synthesis of N-mono-hydroxylated and N-mono-methylated polyamine spider toxins of Agelenopsis aperta and Larinioides folium....
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Effect of hairpin loop structure on reactivity, sequence preference and adduct orientation of a DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumour agent

Org. and Biomol. Chem. - 4 March, 2015 - 17:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02405B, PaperDavid E. Thurston, Higia Vassoler, Paul J. M. Jackson, Colin H. James, Khondaker M. Rahman
Pyrrolobenzodiazepine (PBD) monomer GWL-78 reacts faster with DNA hairpins containing a hexaethylene glycol (HEG) loop compared to hairpins containing a TTT loop due to the greater structural flexibility of the HEG.
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Novel carbapenem chalcone derivatives: Synthesis, cytotoxicity and molecular docking studies

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00197H, PaperDevendar Reddy Kommidi, ramakanth pagadala, Surjyakanta Rana, Parvesh Singh, Suhas Ashok Shintre, Neil Koorbanally, Sreekantha Babu Jonnalagadda, Brenda Moodley
One pot efficient synthetic protocol is described for the synthesis of carbapenem chalcone derivatives using AAPTMS@MCM-41 heterogeneous catalyst. Various substituted aromatic aldehydes were attached to highly chiral and reactive carbapenem...
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Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: Dual stereocontrol with nearly perfect diastereoselectivity

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00322A, CommunicationYi-Shuang Zhao, Qiang Liu, Ping Tian, Jingchao Tao, guoqiang lin
Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of chiral auxiliary and chiral copper complex, has played an important role in achieving the...
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One Pot Synthesis of Diarylfurans from Aryl Esters and PhI(OAc)2 via Palladium-associated Iodonium Ylides

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00273G, CommunicationYong-Sheng Bao, agula bao, Bao Zhaorigetu, Meilin Jia, Menghe Baiyin
The example of palladium-catalyzed intermolecular cyclization for synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and another one...
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Receptor-Templated Stapling of Intrinsically Disordered Peptide Ligands

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00269A, CommunicationConor M. Haney, William Seth Horne
We report here a chemoselective peptide "stapling" method that can be performed on ligand-receptor complexes in situ. An appropriately structured macrocyclic bis-oxime linkage is shown to improve the affinity of...
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Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

Org. and Biomol. Chem. - 4 March, 2015 - 17:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00131E, PaperAlexander V Aksenov, Alexander N Smirnov, Nicolai A Aksenov, Asiyat S Bijieva, Inna V Aksenova, Michael Rubin
PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles,...
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