Org. and Biomol. Chem.

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Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2663-2674
DOI: 10.1039/C3OB42258E, PaperCatarina Carvalho, David Siegel, Martyn Inman, Rui Xiong, David Ross, Christopher J. Moody
Benzofuran- and benzimidazole-quinones are effective inhibitors of the tryptophan metabolizing enzyme indoleamine-2,3-dioxygenase (IDO).
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A computational and experimental study of O-glycosylation. Catalysis by human UDP-GalNAc polypeptide:GalNAc transferase-T2

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2645-2655
DOI: 10.1039/C3OB42569J, PaperHansel Gomez, Raul Rojas, Divya Patel, Lawrence A. Tabak, Jose M. Lluch, Laura Masgrau
GalNAc-T2 catalyses GalNAc O-glycosylation via a front-side nucleophilic attack in which stabilization of the UDP leaving group is crucial.
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Synthesis of carbazole-based hetero-core-modified porphyrins

11 April, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,2656-2662
DOI: 10.1039/C3OB42564A, PaperChihiro Maeda, Motoki Masuda, Naoki Yoshioka
Annulation reaction of a 1,1[prime or minute]-(1,3-butadiyne)-8,8[prime or minute]-(2,5-thiophene)-bridged carbazole dimer 10 provided the carbazole-based isophlorines 11a-11c and 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13.
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Gold-catalyzed tandem Diels-Alder reactions of enynals/enynones with alkenes: generation and trapping of cyclic o-QDMs

11 April, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00321G, PaperShifa Zhu, Lang Hu, Huanfeng Jiang
Gold-catalyzed generation of the highly reactive cyclic o-QDM species and application in preparation of structurally unique propeller-like molecules.
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Enhancing circularly polarised luminescence by extending the [small pi]-conjugation of axially chiral compounds

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00340C, PaperYoko Kitayama, Tomoyuki Amako, Nozomu Suzuki, Michiya Fujiki, Yoshitane IMAI
Circularly polarised luminescence (CPL) and photoluminescence (PL) properties of [small pi]-conjugated (R)- and (S)-2,2-diphenyl-4-biphenanthrol (VAPOL) exhibited an efficient CPL (~1.3[times]10-3) with a quantum yield (ФF) of 0.20 at 376 nm. By...
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Rhodium(III)-Catalyzed Formal Oxidative [4+1] Cycloaddition of Benzohydroxamic Acids and alpha-Diazoester. A Facile Synthesis of Functionalized Benzolactams

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00512K, PaperWing Yiu Yu, Wai-Wing Chan, Zhongyuan Zhou, Hon-Wah Lam, Ka-Yi Man
A Rh(III)-catalyzed oxidative [4+1] cycloaddition of benzohydroxamic acids and alpha-diazoesters is achieved to afford benzolactams in up to 93% yields. With N-OAc amido moiety as a directing group, the ortho-C-H...
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Non-stoichiometric O-acetylation of Shigella flexneri 2a O-specific polysaccharide: synthesis and antigenicity

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C3OB42586J, PaperCharles Gauthier, Pierre Chassagne, Francois-Xavier Theillet, Catherine Guerreiro, Francoise Thouron, Farida Nato, Muriel Delepierre, Philippe J Sansonetti, Armelle Phalipon, Laurence A. MULARD
Synthetic functional mimics of the O-antigen from Shigella flexneri 2a are seen as promising vaccine components against endemic shigellosis. Herein, the influence of the polysaccharide non-stoichiometric di-O-acetylation on antigenicity is...
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Fluorescent Push-pull pH-responsive Probes for Ratiometric Detection of Intracellular pH

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00147H, PaperMartin Ipuy, Guillaume Micouin, Jacques Samarut, Chantal Andraud, Yann Bretonniere, Cyrielle Billon
A family of fluorescent push-pull pH-responsive probes based on 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofurane as strong electron acceptor group is described. Small structural variations allow obtaining pKa ranging from 4.8 to 8.6 underlining the...
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Structure-properties relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: Effect of branching topology and chirality

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00048J, PaperThomas Markowski, Simon Drescher, Annette Meister, Alfred Blume, Bodo Dobner
Three novel diglycerol tetraether lipids with one membrane-spanning chain have been synthesized. These lipids contain only two or four racemic methyl branches at selected positions of the hydrophobic chains in...
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[small beta]-Amyrin synthase from Euphorbia tirucalli. Steric bulk, not the [small pi]-electrons of Phe, at position 474 has a key role in affording the correct folding of the substrate to complete the normal polycyclization cascade

9 April, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00064A, PaperRyousuke Ito, Yukari Masukawa, Chika Nakada, Kanako Amari, Chiaki Nakano, Tsutomu Hoshino
The importance of the steric bulk at 474 residue is described for completion of the cyclization cascade, but not the [small pi]-electrons of the Phe residue.
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Synthesis of homochiral tris-indanyl molecular rods

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00011K, PaperNiels Due Kjeldsen, Erik Daa Funder, Kurt Vesterager Gothelf
Homochiral tris-indanyl molecular rods designed for supramolecular surface self-assembly were synthesized. The chiral indanol moiety was constructed via a Ti-mediated alkyne trimerization. Further manipulations resulted in a homochiral indanol monomer....
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Lipase-Catalyzed Asymmetric Synthesis of Oxathiazinanones through Dynamic Covalent Kinetic Resolution

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00365A, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Lei Hu, Yan Zhang, Olof Ramstrom
A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore...
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Copper-catalyzed bis-arylations of alkenes leading to oxindole derivatives

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00576G, CommunicationLiangliang Shi, Yuyuan Wang, Haijun Yang, Hua Fu
A simple and practical copper-catalyzed approach to oxindole derivatives by copper-catalyzed bis-arylation of N-alkyl-N-phenylacrylamides with diaryliodonium triflates has been developed under mild conditions, and the method is of tolerance towards...
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Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00294F, CommunicationRemya Ramesh, D SRINIVASA REDDY
A simple, fast and efficient method for allylation and propargylation of chlorosilanes through zinc mediation and ultrasound promotion is reported. As a direct application of the resulting bis-allylsilanes, three novel,...
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Silyl alkynylphosphine-boranes: key-precursors of triazolylphosphines via tandem desilylation-Click chemistry

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00397G, PaperCarole Alayrac, Annie Claude Gaumont , Romain Veillard, Ibrahim Abdellah, Jean-Francois Lohier, Elise Bernoud
A versatile synthesis of 1,2,3-triazolyl-4-phosphines from the borane complexes of phosphino-alkynes is reported. The efficiency of the procedure relies on the use of readily available silyl-protected alkynylphosphine-boranes, which were submitted...
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Cap analogs containing 6-thioguanosine - reagents for the synthesis of mRNAs selectively photo-crosslinkable with cap-binding biomolecules

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00059E, PaperMonika Nowakowska, Joanna Kowalska, Franck Martin, Arnaud d'Orchymont, Joanna Zuberek, Maciej Lukaszewicz, Edward Darzynkiewicz, Jacek Jemielity
Numerous biomolecules recognize the 7-methylguanosine cap structure present at the 5' ends of eukaryotic mRNAs. Photo-crosslinking is a valuable technique to study these interactions. We report three anti-reverse cap analogs...
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Direct Olefination of Benzaldehydes into 1,3-diarylpropenes via Copper-Catalyzed Heterodomino Knoevenagel-Decarboxylation-Csp3-H Activation Sequence

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00155A, PaperGonghua Song, yaping zhao, Yanqing Peng, Jiayi Wang, tieqiang zeng, lu sun
Copper-catalyzed direct olefination of benzaldehydes into 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp3-H activation sequence is reported. This method provides a concise and effective route toward the synthesis of unsymmetrical 1,3-diarylpropenes...
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Aggregation-induced Emission Enhancement Upon Al3+ Complexation With Tetrasulfonated Calix[4]bisazacrown Fluorescent Molecular Sensor

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00187G, PaperYibin Ruan, Alexis Depauw, Isabelle Leray
Aggregation-induced emission and aggregation-induced emission enhancement have attracted much attention due to its great potential in real-world applications. Up to now most of the reports are based on the restriction...
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An Enantioselective Strategy for the Total Synthesis of (S)-Tylophorine via Catalytic Asymmetric Allylation and One-Pot DMAP-Promoted Isocyanate Formation/Lewis Acid Catalyzed Cyclization Sequence

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00200H, PaperQingmin Wang, Bo Su, Hui Zhang, Meng Deng
A new asymmetric total synthesis of phenanthroindolizidine alkaloid (S)-tylophorine was reported, which features a catalytic asymmetric allylation of aldehyde and an unexpected one-pot DMAP promoted isocyanate formation and Lewis acid...
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A porphyrin/[small beta]-cyclodextrin conjugated nano-system having a Pan-Lid molecular structure for smart drug carrier applications

9 April, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00393D, PaperPlacido Mineo
In this study, the 5,10,15-tri[p(9-methoxy-triethyleneoxy)phenyl]-20-[p-phenylisophthalate-[small beta]-cyclodextrin] porphyrin, a compound containing a porphyrin and a [small beta]-cyclodextrin unit covalently linked by means of an isophthalic bridge, was synthesized and characterized by NMR, MALDI-TOF...
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