Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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The chemical biology of dimethylsulfoniopropionate

19 January, 2015 - 06:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02407A, Review ArticleJeroen S. Dickschat, Patrick Rabe, Christian A. Citron
This review addresses synthesis, biosynthesis, transport and degradation of dimethylsulfoniopropionate and its derivatives.
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Expedient access to [small alpha],[small beta]-difunctionalized azepenes using [small alpha]-halo eneformamides: application to the one-pot synthesis of 2-benzazepanes

19 January, 2015 - 06:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02183E, PaperDaniel P. Bassler, Laura Spence, Amir Alwali, Oliver Beale, Timothy K. Beng
The regioselective synthesis of [small alpha],[small beta]-difunctionalized (alkenyl, aryl, sulfonyl, allyl, or alkynyl) azepenes has been accomplished through [small alpha]-halo eneformamides.
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Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02408G, PaperPei-Pei Yeh, David S. B. Daniels, Charlene Fallan, Eoin Gould, Carmen Simal, James E. Taylor, Alexandra M. Z. Slawin, Andrew D. Smith
The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented.
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Mixed alkyl aryl phosphonate esters as quenched fluorescent activity-based probes for serine proteases

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02444C, PaperSevnur Serim, Philipp Baer, Steven H. L. Verhelst
The synthesis of quenched fluorescent activity-based probes for serine proteases based on a phosphonate reactive group is reported.
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Energy transfer between amphiphilic porphyrin polymer shells and upconverting nanoparticle cores in water-dispersible nano-assemblies

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02401J, PaperT. Wu, S. Kaur, N. R. Branda
The synthesis and optical properties of water-dispersible nano-assemblies containing upconverting nanoparticles (UCNPs) and porphyrin molecules using a one-pot method is described.
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Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02440K, PaperMarek Stankevic
Birch reduction of symmetrical diarylphosphinous acid-borane amides possessing a chiral amido group, proceeds with diastereoselectivity up to 72%.
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A supramolecular topical gel derived from a non-steroidal anti-inflammatory drug, fenoprofen, is capable of treating skin inflammation in mice

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02344G, PaperJoydeb Majumder, Pavani Yedoti, Parthasarathi Dastidar
A small [small beta]-dipeptide functionalized fenoprofen bioconjugate forms supramolecular gel with menthol containing methylsalicylate solvent. The resulting gel shows topical self-delivery application in treating imiquimod induced skin inflammation in mice.
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Fluoride binding in water with the use of micellar nanodevices based on salophen complexes

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02298J, PaperFlore Keymeulen, Paolo De Bernardin, Ilaria Giannicchi, Luciano Galantini, Kristin Bartik, Antonella Dalla Cort
Uranyl-salophen complexes incorporated into micelles are evaluated as supramolecular nanosystems for the binding of fluoride in water.
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A facile and high-yield formation of dipyrrin-boronic acid dyads and triads: a light-harvesting system in the visible region based on the efficient energy transfer

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02351J, PaperMasaki Yamamura, Shinya Yazaki, Motofumi Seki, Yasunori Matsui, Hiroshi Ikeda, Tatsuya Nabeshima
Artificial light-harvesting systems, Ar,O-BODIPY dyads and triads conjugated with a light harvester, were synthesized in high yield by the reaction of an N2O2-type dipyrrin with boronic acids.
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An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane

15 January, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02109F, PaperMaria Moccia, Robert J. Wells, Mauro. F. A. Adamo
A two-step preparation of 3-methyl-4-nitro-5-alkylethenyl isoxazoles is herein reported. These were reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee).
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Highly selective and sensitive detection of glutathione using mesoporous silica nanoparticles capped with disulfide-containing oligo(ethylene glycol) chains

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1017-1021
DOI: 10.1039/C4OB02083A, CommunicationSameh El Sayed, Cristina Gimenez, Elena Aznar, Ramon Martinez-Manez, Felix Sancenon, Maurizio Licchelli
Mesoporous silica nanoparticles loaded with safranin O and capped with disulfide-containing oligo(ethylene glycol) chains were used for the selective and sensitive fluorimetric detection of GSH.
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A chiral borane catalyzed asymmetric hydrosilylation of imines

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1013-1016
DOI: 10.1039/C4OB02419B, CommunicationXiaxia Zhu, Haifeng Du
An enantioselective hydrosilylation of imines was achieved using an in situ generated chiral borane to furnish amines with up to 82% ee.
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Water-soluble aryl-extended calix[4]pyrroles with unperturbed aromatic cavities: synthesis and binding studies

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1022-1029
DOI: 10.1039/C4OB02108H, PaperD. Hernandez-Alonso, S. Zankowski, L. Adriaenssens, P. Ballester
An aryl-extended calix[4]pyrrole receptor with four carboxylic groups at the lower rim binds N-oxides in water with high stability constants.
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Investigation of end processing and degradation of premature tRNAs and their application to stabilization of in vitro transcripts in wheat germ extract

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1008-1012
DOI: 10.1039/C4OB02221A, CommunicationAtsushi Ogawa, Yasunori Doi
We investigated the end processing and degradation of premature tRNAs in wheat germ extract (left), which led to the findings of end protectors for efficiently stabilizing an in vitro transcript (purple, right).
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Developing piperine towards TRPV1 and GABAA receptor ligands - synthesis of piperine analogs via Heck-coupling of conjugated dienes

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,990-994
DOI: 10.1039/C4OB02242D, CommunicationLaurin Wimmer, David Schonbauer, Peter Pakfeifer, Angela Schoffmann, Sophia Khom, Steffen Hering, Marko D. Mihovilovic
Synthetic analogs of piperine, the pungent alkaloid of black pepper, were identified as selective ligands for either GABAA or TRPV1 receptors.
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An expedient approach to 1,2-dihydroisoquinoline derivatives via cobalt catalysed 6-endo dig cyclization followed by Mannich condensation of o-alkynylarylaldimines

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1000-1007
DOI: 10.1039/C4OB02036G, Communication Urvashi, Gaurav K. Rastogi, Sandeep K. Ginotra, Alka Agarwal, Vibha Tandon
A highly effective 6-endo dig cyclisation of o-alkynyl aldimines to 1,2-dihydroisoquinolines has been described via direct and nitro Mannich condensation using inexpensive and readily available cobalt chloride as catalyst.
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Ruthenium-catalyzed direct C3 alkylation of indoles with [small alpha],[small beta]-unsaturated ketones

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1254-1263
DOI: 10.1039/C4OB02124J, PaperShuai-Shuai Li, Hui Lin, Xiao-Mei Zhang, Lin Dong
In this paper, a simple and highly efficient ruthenium-catalyzed direct C3 alkylation of indoles with various [small alpha],[small beta]-unsaturated ketones without chelation assistance has been developed.
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Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1243-1248
DOI: 10.1039/C4OB01844C, PaperHaipin Zhou, Kuo Gai, Aijun Lin, Jinyi Xu, Xiaoming Wu, Hequan Yao
A palladium-catalyzed oxidative cross-coupling reaction between azole-4-carboxylates and indoles forming 5-(3-indolyl)azoles with excellent regioselectivity has been developed.
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Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1249-1253
DOI: 10.1039/C4OB02377C, PaperH. Muchalski, L. Xu, N. A. Porter
We report here that H-atom tunneling facilitates the propagation step in the tocopherol-mediated peroxidation (TMP) of 7-dehydrocholesterol. This process likely becomes a major propagation pathway when radical intermediates are isolated in cellular organelles or lipid particles such as low-density lipoproteins. In TMP of 7-DHC and deuterium-reinforced 7-DHC, the KIE of removing hydrogen/deuterium at C9 was found to be 21 +/- 1.
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Metal-catalyzed formation of 1,3-cyclohexadienes: a catalyst-dependent reaction

13 January, 2015 - 04:54

Org. Biomol. Chem., 2015, 13,1225-1233
DOI: 10.1039/C4OB01922A, PaperShifa Zhu, Xiaobing Huang, Tian-Qi Zhao, Tongmei Ma, Huanfeng Jiang
A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was used as the catalyst, however, another isomer 2,4-cyclohexadiene (2,4-CHD) was furnished instead.
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