Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1488-1494
DOI: 10.1039/C3OB41421C, PaperSilvia Bezer, Masaomi Matsumoto, Michael W. Lodewyk, Stephen J. Lee, Dean J. Tantillo, Michel R. Gagne, Marcey L. Waters
A high-throughput screening method is used for identification of new catalytic functionalities for transesterification reaction in organic solvent.
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Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1603-1610
DOI: 10.1039/C3OB41982G, PaperF. Di Maria, I. E. Palama, M. Baroncini, A. Barbieri, A. Bongini, R. Bizzarri, G. Gigli, G. Barbarella
Newly synthesized cell-permeant thiophene fluorophores experience a distinct fate inside live cells: from cytoplasm staining to selective tagging of globular proteins.
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Callyspongisines A-D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1579-1584
DOI: 10.1039/C4OB00091A, PaperFabien Plisson, Pritesh Prasad, Xue Xiao, Andrew M. Piggott, Xiao-cong Huang, Zeinab Khalil, Robert J. Capon
An Australian Callyspongia sp. yielded the new bromopyrrole alkaloids callyspongisines A-D. Callyspongisine A is only the second reported example of a natural imino-oxazoline and the first to feature a spiro heterocyclic framework.
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Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1570-1578
DOI: 10.1039/C3OB42516A, PaperRobert E. Thompson, Frederic Collin, Anthony Maxwell, Katrina A. Jolliffe, Richard J. Payne
Using a combination of solid-phase peptide synthesis and fragment assembly strategies a library of full-length and truncated analogues of the antibacterial post-translationally modified peptide microcin B17 have been synthesised. Both antibacterial and DNA gyrase poisoning activities are also described for the synthetic analogues.
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Synthesis, structure and inhibitory activity of a stereoisomer of oseltamivir carboxylate

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1561-1569
DOI: 10.1039/C3OB42069H, PaperAndrea Sartori, Luca Dell'Amico, Lucia Battistini, Claudio Curti, Silvia Rivara, Daniele Pala, Philip S. Kerry, Giorgio Pelosi, Giovanni Casiraghi, Gloria Rassu, Franca Zanardi
A versatile asymmetric synthesis of the C-4 epimer of oseltamivir carboxylate (OC) is reported. A marked drop in inhibitory activity toward influenza virus neuraminidase was observed and rationalized.
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Identification of BP16 as a non-toxic cell-penetrating peptide with highly efficient drug delivery properties

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1652-1663
DOI: 10.1039/C3OB42422G, PaperMarta Soler, Marta Gonzalez-Bartulos, David Soriano-Castell, Xavi Ribas, Miquel Costas, Francesc Tebar, Anna Massaguer, Lidia Feliu, Marta Planas
BP16 is a non-toxic cell-penetrating peptide with high cellular uptake in vitro. This peptide is an efficient vector for the delivery of therapeutic agents into cells, as has been shown for the anticancer drug chlorambucil.
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Ring contraction of 1,3-diphenylbenzo[1,2,4]triazinyl radicals to 1,2-diphenylbenzimidazoles

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1641-1648
DOI: 10.1039/C3OB42130A, PaperAndrey A. Berezin, Panayiotis A. Koutentis
Optimized conditions for the reductive ring contraction of benzotriazinyl radicals and related analogues afford benzimidazoles in near quantitative yields.
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Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1664-1670
DOI: 10.1039/C3OB42396D, PaperChada Raji Reddy, Gaddam Krishna, Motatipally Damoder Reddy
A new approach for the synthesis of 5-substituted 3-furoates from MBH-acetates of acetylenic aldehydes has been developed. This methodology provided an entry to Elliott's alcohol, a key subunit of resmethrin.
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Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1547-1550
DOI: 10.1039/C3OB42486C, CommunicationMing Yu Jin, Sun Min Kim, Hui Mao, Do Hyun Ryu, Choong Eui Song, Jung Woon Yang
Chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio.
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A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1633-1640
DOI: 10.1039/C3OB42209G, PaperHao Liu, Ruijiao Chen, Xiaochuan Chen
A flexible protocol for the asymmetric syntheses of renieramycin-type alkaloids featuring a temperature-dependent Pictet-Spengler cyclization and the subsequent lactamization is described.
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A fluorene-based material containing triple azacrown ether groups: synthesis, characterization and application in chemosensors and electroluminescent devices

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1419-1429
DOI: 10.1039/C3OB42054J, PaperChia-Shing Wu, Ying-Ju Lin, Yun Chen
A novel fluorene-based FTC containing triple azacrown ether groups is applied as a chemical sensor and as an electron injection layer simultaneously.
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NMR elucidation of the role of Mg2+ in the structure and stability of the conserved RNA motifs of the EMCV IRES element

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1495-1509
DOI: 10.1039/C3OB41840E, PaperSadia Mohammed, Marie M. Phelan, Usman Rasul, Vasudevan Ramesh
NMR structure of the highly conserved and functionally significant 16mer RNA motif endowed with a classic "GNRA" tetraloop of the novel EMCV IRES element.
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Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1475-1487
DOI: 10.1039/C3OB42380H, PaperElisabeth Nagaradja, Floris Chevallier, Thierry Roisnel, Vincent Dorcet, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Florence Mongin
1-Aryl-1H-benzotriazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based Li-Zn combination. The regioselectivity has been discussed in the light of DFT-calculated CH acidities (THF solution).
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Measurement of supramolecular effective molarities for intramolecular H-bonds in zinc porphyrin-imidazole complexes

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1440-1447
DOI: 10.1039/C3OB42246A, PaperMichael A. Jinks, Hongmei Sun, Christopher A. Hunter
Effective molarities measured for the formation of H-bonds in a variety of zinc porphyrin-imidazole complexes are all between 3 mM and 200 mM, and the values measured for flexible and rigid ligand systems are comparable.
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Water/alcohol soluble electron injection material containing azacrown ether groups: synthesis, characterization and application to enhancement of electroluminescence

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1430-1439
DOI: 10.1039/C3OB42070A, PaperChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo, Yun Chen
A copoly(p-phenylene) containing pendant azacrown ether and ethylene glycol ether groups was prepared as a highly efficient electron injection layer for PLEDs.
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Total synthesis of alkyl citrate natural products

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1367-1382
DOI: 10.1039/C3OB42231C, Review ArticleMark A. Rizzacasa, Dayna Sturgess
This review highlights the synthesis of members of the alkyl citrate family of natural products. The focus is on the stereoselective construction of the alkyl citrate moiety common to these compounds.
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Copper-catalyzed annulation of [small alpha]-substituted diazoacetates with 2-ethynylanilines: the direct synthesis of C2-functionalized indoles

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1387-1390
DOI: 10.1039/C3OB42350F, CommunicationGang Liu, Guangyang Xu, Jian Li, Dong Ding, Jiangtao Sun
Copper-catalyzed direct annulation of [small alpha]-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yields.
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A concise formation of N-substituted 3,4-diarylpyrroles - synthesis and cytotoxic activity

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1518-1524
DOI: 10.1039/C3OB42309C, PaperMaxim Egorov, Bernard Delpech, Genevieve Aubert, Thierry Cresteil, Maria Concepcion Garcia-Alvarez, Pascal Collin, Christian Marazano
Sequential condensation of a phenacyl halide with a primary amine and a phenylacetaldehyde led to N-substituted 3,4-diarylpyrroles. Synthesis of analogs of the marine alkaloid halitulin and cytotoxic studies are reported.
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Enzyme-controllable F-NMR turn on through disassembly of peptide-based nanospheres for enzyme detection

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1383-1386
DOI: 10.1039/C3OB42078G, CommunicationJie Gao, Yang Shi, Youzhi Wang, Yanbin Cai, Jie Shen, Deling Kong, Zhimou Yang
The enzyme tyrosinase could trigger the disassembly of peptide-based nanospheres, resulting in F-NMR signal turning on.
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Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers

17 February, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,1463-1474
DOI: 10.1039/C3OB42270D, PaperStephanie S. Le Corre, Mathieu Berchel, Nawal Belmadi, Caroline Denis, Jean-Pierre Haelters, Tony Le Gall, Pierre Lehn, Tristan Montier, Paul-Alain Jaffres
The synthesis of a series of new cationic lipids possessing two different lipid chains is detailed. The transfection efficacies have shown the interest to associate a phytanyl chain with either, a lauryl or oleyl chain.
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