Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides

3 hours 1 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01883D, CommunicationBani Kanta Sarma, Xiaodan Liu, Hao Wu, Yu Gao, Thomas Kodadek
Solid phase synthesis of 1,3,4-oxadiazin-5(6R)-one and 1,3,4-oxadiazol-2-one scaffolds from resin-bound acyl hydrazides is described.
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Enantioselective synthesis of [small alpha]-benzylated lanthionines and related tripeptides for biological incorporation into E. coli peptidoglycan

3 hours 1 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01476F, PaperThibaut Denoel, Astrid Zervosen, Christian Lemaire, Bernard Joris, Mireille Herve, Didier Blanot, Guillermo Zaragoza, Andre Luxen
The synthesis of modified tripeptides (S)-Ala-[gamma]-(R)-Glu-X, where X = (R,S) or (R,R) diastereomers of [small alpha]-benzyl or [small alpha]-(4-azidobenzyl)lanthionine, was carried out.
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Enantioselective Total Synthesis of Sch-725674

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02136C, PaperKrishna P Kaliappan, Kota Ramakrishna
An enantioselective total synthesis of Sch-725674, a unique 14-membered macrolactone, has been accomplished in 13 steps. The step-wise dithiane alkylation served as a strategic step to assemble the northern and...
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Palladium(0)-Catalyzed Synthesis of Cyclic Glucosides

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01975J, PaperXin Huang, Chunling Fu, Shengming Ma
A highly regio- and stereo-selective synthesis of cyclic [small beta]-D-glucosides 3 via Pd(0)-catalyzed coupling cyclization of allenyl [small beta]-D-glucoside 1 and organic iodides in the yields of 20~38% is reported. After the...
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Design and Synthesis of a Mitochondria-Targeting Carrier for Small Molecule Drugs

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01981D, CommunicationJunyan Han, Dae Hoon Lee, Ching-Hsuan Tung, Daniel Lee
A novel mitochondria-targeting carrier QCy7HA was developed. QCy7HA transported the covalently attached doxorubicin (DOX) to mitochondria specifically. The conjugate limited the effects of P-glycoprotein (Pgp) efflux pumps of multidrug-resistant cells...
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Kinetic evaluation of glucose 1-phosphate analogues with a thymidylyltransferase using a continuous coupled enzyme assay

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02057J, PaperStephanie M. Forget, Alison Jee, Deborah A Smithen, Rajendra Jagdhane, Stephen A Beaton, Raymond T Syvitski, David RJ Palmer, David L Jakeman
Cps2L, a thymidylytransferase, is the first enzyme in Streptococcus pneumoniae L-rhamnose biosynthesis and an antibacterial target. We herein report the evaluation of six sugar phosphate analogues selected to further probe...
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Rhodium(II)-Catalyzed Intramolecular Formal [4+3] Cycloadditions of Dienyltriazoles: Rapid Access to Fused 2,5-Dihydroazepines

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01910E, PaperYefeng Tang, Yu Tian, Yuanhao Wang, Hai Shang, Xudong Xu
Rhodium(II)-catalyzed intramolecular [4+3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-Cope rearrangement.
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Developing a Targeting System for Bacterial Membranes: Measuring Receptor-Phosphatidylglycerol Interactions with 1H NMR, ITC, and Fluorescence Correlation Spectroscopy

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01895H, PaperAmanda Alliband, Zifan Wang, Christopher Thacker, Douglas S. English, Dennis Huntington Burns
An ammonium picket porphyrin that targets bacterial membranes has been prepared and shown to bind to phosphatidylglycerol (PG), a bacterial lipid, when the lipid was in solution, contained within synthetic...
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Highly Efficient Modular Metal-Free Synthesis of 3-Substituted 2-Quinolones

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02131B, CommunicationAlexander V Aksenov, Alexander N Smirnov, Nicolai A Aksenov, Inna V Aksenova, Asiyat S Bijieva, Michael Rubin
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
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Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral [small alpha]-substituted carboxylic acids from [small alpha]-substituted [small alpha]-[small beta] unsaturated aldehydes.

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02282C, PaperTanja Knaus, Francesco G Mutti, Luke Humphreys, Nicholas J Turner, Nigel S Scrutton
Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, [small alpha]-[small beta] unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkanes...
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L-Valine Derived Chiral N-Sulfinamides as Effective Organocatalysts for the Asymmetric Hydrosilylation of N-Alkyl and N-Aryl Protected Ketimines

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01257G, PaperChao Wang, Li Zhou, Jian Sun, Xinjun Wu
L-Valine derived N-sulfinamides have been developed as efficient enantioselective Lewis basic organocatalysts for the asymmetric reduction of N-aryl and N-alkyl ketimines with trichlorosilane. Catalyst 3c afforded up to 99% yield...
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The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02105C, PaperSteffen Glockner, Duc N Tran, Richard Ingham, Sabine Fenner, Zoe E Wilson, Claudio Battilocchio, Steven V Ley
A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature with inversion of stereochemistry from [small beta]-hydroxy amides using...
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Preparation of Asymmetrical Polyynes by a Solid-Supported Glaser-Hay Reaction

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02196G, PaperJessica Lampkowski, Corinn Durham, Marshall Padilla, Douglas Dean Young
Polyynes exhibit both unique photophysical properties and biological activities, obviating the necessity for efficient syntheses towards these core structures. A novel methodology for the construction of highly conjugated asymmetrical polyynes...
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Virtual screening and biological evaluation of novel small molecular inhibitors against protein arginine methyltransferase 1 (PRMT1)

3 hours 1 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01591F, PaperYiqian Xie, Ran Zhou, Fulin Lian, Yan Liu, Limin Chen, Zhe Shi, Naixia Zhang, Mingyue Zheng, Bairong Shen, Hualiang Jiang, Zhongjie Liang, Cheng Luo
Two novel inhibitors against PRMT1 were identified through virtual screening and biochemical assays. Their binding with PRMT1 was validated and they also displayed an anti-proliferation effect in three cancer cell lines.
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6-Substituted 1,2-benzoxathiine-2,2-dioxides are Isoform-Selective Inhibitors Towards Human Carbonic Anhydrases IX, XII and VA

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02155J, CommunicationFabrizio Carta, Muhammet tanc, Andrea Scozzafava, Claudiu Supuran
A series of 6-substituted 2-benzoxathiine-2,2-dioxides were synthesized starting from 2,5-dihydroxybenzaldehyde, and then screened in vitro for their inhibition profiles against five human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms. All the...
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A PEPTIDE TOPOLOGICAL TEMPLATE FOR THE DISPERSION OF [60]FULLERENE IN WATER

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02102A, CommunicationMiriam Mba, Alessandro Moretto, Silvia Bartocci, Daniela Mazzier
Solubilization of [60]fullerene in water is a major challenge for biological and medical applications. To this purpose in this communication we describe for the first time a new dispersing system...
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A highly efficient and eco-friendly method for synthesis of 1,3-indandione ring-fused 3-oxindoles bearing two contiguous quaternary stereocenters via Aldol reaction in aqueous media

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02103G, PaperXiong-Li Liu, Bo-Wen Pan, Wen-Hui Zhang, Chao Yang, Jun Yang, Yang Shi, Ting-Ting Feng, Ying Zhou, Weicheng Yuan
A highly efficient and environmentally benign method for the synthesis of oxindoles featuring two contiguous quaternary carbon centers via Aldol reaction starting from various 3-substituted oxindoles has been established. A...
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Cyclen-based cationic lipids containing pH-sensitive moiety as gene delivery vectors

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01856G, PaperXiao-Qi Yu, Zheng Huang, Yan-Hong Liu, Yi-Mei Zhang, Ji Zhang, Qiang Liu
A series of novel cationic lipids based on 1, 4, 7, 10-tetrazacyclododecane (cyclen) with imidazole group as pH-sensitive moiety and various aliphatic long chains were designed and synthesized. Cationic liposomes...
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Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones

3 hours 1 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02146K, CommunicationSubhas Chandra Pan, Buddhadeb Mondal
Primary amino acids are found to be good enantioselective catalysts for the direct asymmetric Mannich reaction between 2-amino acetophenone and aldehydes. The 2-aryl-2,3-dihydro-4-quinoline products are obtained in moderate to good...
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A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

3 hours 1 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02107J, CommunicationChou-Hsiung Chen, Sivaneswary Genapathy, Peter M. Fischer, Weng C. Chan
Utilising a chiral auxiliary-facilitated Strecker amino acid synthesis strategy, indole-substituted (S)-tryptophans have been obtained from corresponding indoles; the former in turn were used for the synthesis of a potent antibacterial agent, argyrin and its analogues.
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