Org. and Biomol. Chem.

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The Synthesis of Head-to-Tail Cyclic Sulfono-[gamma]-AApeptides

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02232G, CommunicationHaifan Wu, Fengyu She, Wen-Yang Gao, Austin Prince, Yaqiong Li, Lulu Wei, Allison Mercer, Lukasz Wojtas, Shengqian Ma, Jianfeng cai
We report an efficient method for the preparation of unprecedented head-to-tail cyclic sulfono-[gamma]-AApeptides. Following this method, a number of cyclic sequences bearing two to five subunits were efficiently synthesized. In...
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Direct oxidative coupling of thiols and benzylic ethers via C(sp3)-H activation and C-O cleavage to lead thioesters

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02250E, CommunicationJie Feng, Meifang Lv, Guoping Lu, Chun Cai
An unprecedented C-S formation method via the direct oxidative C(sp3)-H bond functionalization and C-O cleavage of benzylic ethers was developed. Various thioesters including thioester structure containing drug intermediate could be...
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Palladium Catalyzed unactivated [small beta]-methylene C(sp3)-H Bond Alkenylation of Aliphatic Amides and Application in A sequential C(sp3)-H/C(sp2)-H Bond Alkenylation

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02389G, Communicationyu rao, gang shan, guiyi huang
A palladium(II) catalyzed [small beta]-methylene C(sp3)-H bond alkenylation of acyclic aliphatic amides with alkenyl halides has been developed. Both (E)-olefin and (Z)-olefin can be readily accessed by this method and a...
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Unprecedented One-Pot Sequential Thiolate Substitutions of 8-methylthio-BODIPY under Mild Conditions leading to a Red Emissive BODIPY Dye 3,5,8-tris(PhS)-BODIPY.

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01892C, CommunicationKeith Pannell, Alejandro Jose Metta Magana, Eduardo Pena-Cabrera, Robinson Roacho
The simple reaction of phenylthiol with 8-MeS-BODIPY (1) in dichloromethane was readily accomplished to form 8-PhS-BODIPY (2). If the reaction is performed in THF 3,8-bis(phenylthio)-BODIPY (3) and 3,5,8-tris(phenylthio)-BODIPY (4) are...
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The synthesis of [18F]pitavastatin as a tracer for hOATP using the Suzuki coupling

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01953A, PaperYusuke Yagi, Hiroyuki Kimura, Kenji Arimitsu, Masahiro Ono, Kazuya Maeda, Hiroyuki Kusuhara, Tetsuya Kajimoto, Yuichi Sugiyama, Hideo Saji
Fluorine-18 labeled radiotracers, such as [18F]fluorodeoxyglucose, can be used as practical diagnostic agents in positron emission tomography (PET). Furthermore, the properties of pharmaceuticals can be enhanced significantly by the introduction...
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Studies Towards Asymmetric Synthesis of 4(S)-11-Dihydroxydocosahexaenoic acid (diHDHA) Featuring Cross-Coupling of Chiral Stannane under Mild Conditions

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02324B, CommunicationRUI WANG, John Falck
The presented discoveries herein is to utilize the mild Stille coupling reactions of chiral [small alpha]-generated stannane, which is previously developed by our group. We subsequently assembled these three segments and...
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The Development of a Complementary Pathway for the Synthesis of Aliskiren

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01963F, PaperFu-She Han, Le-Le Li, Jin-Ying Ding, Lianxun Gao
The synthesis of aliskiren (1), a recently marketed drug for the treatment of hypertensive disease, is presented. The focus of our synthetic effort is the development of an efficient pathway...
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Characterizations of cationic [gamma]-carbolines binding with double-stranded DNA by spectroscopic methods and AFM imaging

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01905A, PaperTao Jia, Jing Wang, Peng GUO, Junping Yu
Two cationic [gamma]-carbolines, MPII and DPII, were synthesized, and the DNA binding properties of the cationic [gamma]-carbolines were elucidated. Through a series of experiments, we proved that the two cationic...
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[gamma]-CYCLODEXTRIN MODULATES CHEMICAL REACTIVITY BY MULTIPLE COMPLEXATION

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02113D, PaperLuis Garcia Rio, Josefa Fernandez-Rosas, Marcia Pessego, Marjorie Cepeda, Nuno Basilio, Mercedes Parajo, Pedro Rodriguez-Dafonte
Multiple complexation by [gamma]-CD have been studied both by self-diffusion coefficients (DOSY) and chemical kinetic experiments (using 4-methoxybenzenesulfonyl chloride, MBSC, solvolysis as a chemical probe). Surfactant addition as third component...
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Design and Synthesis of Troger's Base Ditopic Receptors: Host-Guest Interactions, a Combined Theoretical and Experimental Study

21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02266A, PaperManjula Alla, Bhaskar Reddy Manda, Shailaja Myadaraboina, J. Richard Premkumar, G. Narahari Sastry, Sirisha Katkuri, Sarma VS Akella
Two flexible Troger's base ditopic receptors C4TB and C5TB incorporating monoaza crown ether were designed and synthesized for bisammonium ion complexation. Comprehensive study of host-guest interactions were established by 1H...
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Synthesis and Tautomerization of Hydroxylated Isoflavones Bearing Heterocyclic Hemi-Aminals

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02137A, PaperMykhailo M Frasinyuk, Svitlana P Bondarenko, Volodymyr P Khilya, Chunming Liu, David Watt, Vitaliy M Sviripa
The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of...
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Modulation of the charge transfer and photophysical properties in non-fused tetrathiafulvalene-benzothiadiazole derivatives

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02100B, PaperFlavia Pop, Sabine Seifert, Jihane Hankache, Jie Ding, Andreas Hauser, Narcis Avarvari
Bis(thiomethyl)- and bis(thiohexyl)-tetrathiafulvalene-bromo-benzothiadiazoles, containing electron donor tetrathiafulvalene (TTF) and electron acceptor benzothiadiazole (BTD) units, have been prepared by Stille coupling reactions between the TTF-SnMe3 precursors and BTD-Br2. In another series...
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Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02185A, PaperRalph Appel, Sebastian Tacke, Jurgen Klingauf, Pol Besenius
We report the synthesis of a series of anionic dendritic peptide amphiphiles of increasing hydrophobic character. By establishing state diagrams we describe their pH and ionic strength triggered self-assembly into...
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Interactions of Arene Ruthenium Metallaprisms with Human Proteins

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02194K, PaperLydia E. H. Paul, Bruno Therrien, Julien Furrer
Interactions between three hexacationic arene ruthenium metallaprisms, ([(p-cymene)6Ru6(tpt)2(dhnq)3]6+, [(p-cymene)6Ru6(tpt)2(dhbq)3]6+ and [(p-cymene)6Ru6(tpt)2(oxa)3]6+, and a series of human proteins including human serum albumin, transferrin, cytochrome c, myoglobin and ubiquitin have been studied...
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Hydroformylation of olefins and reductive carbonylation of aryl halides with syngas formed ex situ from dehydrogenative decarbonylation of hexane-1,6-diol

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01958J, PaperRobert Madsen, Stig Holden Christensen, Esben Paul Krogh Olsen, Jascha Rosenbaum
A variety of primary alcohols have been investigated as convenient substrates for the ex situ delivery of carbon monoxide and molecular hydrogen in a two-chamber reactor. The gaseous mixture is...
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Indole-Based Novel Small Molecules for the Modulation of Bacterial Signalling Pathways

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02096K, PaperNripendra Nath Biswas, Samuel Kutty, Nicolas Barraud, George M Iskander, A/Prof Renate Griffith, Scott Rice, Mark DP Willcox, David StClair Black, Naresh Kumar
Gram-negative bacteria such as Pseudomonas aeruginosa use N-acylated L-homoserine lactones (AHLs) as autoinducers (AIs) for quorum sensing (QS), a major regulatory and cell-to-cell communication system for social adaptation, virulence factor...
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Selective detection of Al3+ and citric acid with a fluorescent amphiphile

19 November, 2014 - 15:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02095B, PaperZiya Kostereli, Kay Severin
The assembly and disassembly of a fluorescent amphiphile by Al3+ and citrate, respectively, can be used to sense these analytes by fluorescence spectroscopy.
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A Mild Copper-catalyzed Aerobic Oxidative Thiocyanation of Arylboronic Acids with TMSNCS

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02208D, CommunicationNan Sun, Liusheng Che, Weimin Mo, Baoxiang Hu, Zhenlu Shen, Xinquan Hu
A facile and efficient transformation of arylboronic acids to their corresponding arylthiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under...
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Bioorthogonal labelling of 3-nitrotyrosine in peptides and proteins through diazotisation mediated azidation

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02133A, CommunicationJohn Yee Ng, Jason Wing Hon Wong
A new chemical derivatisation method to functionalise peptide and protein bound 3-nitrotyrosine residues is described. By transforming 3-nitrotyrosine to 3-azidotyrosine, the method enables 'click chemistry'-based labelling of the 3-nitrotyrosine residues...
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Cationic dialkylarylphosphates: new family of bio-inspired cationic lipids for gene delivery.

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01770F, PaperPaul-Alain Jaffres, Stephanie Sandra Le Corre, Nawal Belmadi, Mathieu Berchel, Tony Le GAll, Jean-Pierre Haelters, Pierre Lehn, Tristan Montier
In this work, that aims to synthesize and evaluate new cationic lipids as vectors for gene delivery, we report the synthesis of a series of cationic lipids in which a...
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