Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Fluorinated hydroxypiperidines as selective [small beta]-glucosidase inhibitors

28 May, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,5983-5996
DOI: 10.1039/C5OB00721F, PaperClothilde Le Guen, Teresa Mena-Barragan, Carmen Ortiz Mellet, David Gueyrard, Emmanuel Pfund, Thierry Lequeux
Synthesis and glucosidase inhibitory activity of piperidines revealed a reverse selectivity between F- and H-alkenes.
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Heparan sulfate phage display antibodies recognise epitopes defined by a combination of sugar sequence and cation binding

28 May, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,6066-6072
DOI: 10.1039/C5OB00564G, PaperValeria Solari, Timothy R. Rudd, Scott E. Guimond, Andrew K. Powell, Jeremy E. Turnbull, Edwin A. Yates
Sugar sequence and M+ binding defines HS phage display Ab recognition.
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HIV-1 drug discovery: targeting folded RNA structures with branched peptides

28 May, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,5848-5858
DOI: 10.1039/C5OB00589B, Review ArticleJessica E. Wynn, Webster L. Santos
Branched peptides utilize multivalent binding to selectively recognize HIV RNA.
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Synthesis of nisin AB dicarba analogs using ring-closing metathesis: influence of sp3versus sp2 hybridization of the [small alpha]-carbon atom of residues dehydrobutyrine-2 and dehydroalanine-5 on the lipid II binding affinity

28 May, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,5997-6009
DOI: 10.1039/C5OB00336A, PaperJack C. Slootweg, Eric. F. van Herwerden, Mark. F. M. van Doremalen, Eefjan Breukink, Rob M. J. Liskamp, Dirk T. S. Rijkers
An alkane-bridged bicyclic nisin mimic with [small alpha],[small beta]-dehydroamino acids in the backbone was synthesized.
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Facile synthesis of 4- and 7-azaindoles from the corresponding imines by palladium-catalyzed cascade C-C and C-N coupling

28 May, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,6047-6058
DOI: 10.1039/C5OB00720H, PaperNgo Nghia Pham, Thanh Tuan Dang, Ngoc Thang Ngo, Alexander Villinger, Peter Ehlers, Peter Langer
The cyclization of 2,3-dihalopyridines with readily available imines provides a convenient and regioselective approach to 4- and 7-azaindoles.
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Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,6082-6102
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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Ring size in cyclic endomorphin-2 analogs modulates receptor binding affinity and selectivity

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,6039-6046
DOI: 10.1039/C5OB00565E, PaperJustyna Piekielna, Alicja Kluczyk, Luca Gentilucci, Maria Camilla Cerlesi, Girolamo Calo', Csaba Tomboly, Krzysztof Lapinski, Tomasz Janecki, Anna Janecka
A series of endomorphin-2 cyclic analogs with 17- to 14-membered rings was synthesized and evaluated in terms of opioid affinity and selectivity. Conformational studies enabled us to rationalize biological results.
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Binding of pixantrone to DNA at CpA dinucleotide sequences and bulge structures

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5972-5982
DOI: 10.1039/C5OB00526D, PaperShyam K. Konda, Haiqiang Wang, Suzanne M. Cutts, Don R. Phillips, J. Grant Collins
The anti-cancer drug pixantrone intercalates predominantly from the minor groove at adenine bulge sites, but with approximately equal frequency from the minor and major grooves at CpA sites.
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Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,6031-6038
DOI: 10.1039/C5OB00499C, PaperLucas Cunha Dias de Rezende, Shaiani Maria Gil de Melo, Stijn Boodts, Bram Verbelen, Wim Dehaen, Flavio da Silva Emery
Thiocyanation and formation of thioalkylated BODIPYs is a simple and reliable way for their chemical modification and photophysical tuning.
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A mechanistic investigation of anti-elimination in (Z)-1,2-bis(arylseleno)-1-alkenes and their sulfur analogs

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5964-5971
DOI: 10.1039/C5OB00490J, PaperAsami Tarao, Yukako Tabuchi, Eri Sugimoto, Miki Ikeda, Hitomi Uchimoto, Kenji Arimitsu, Hiroyuki Kimura, Ikuo Kawasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kiyoharu Nishide
Selenoxide anti-elimination in (Z)-1,2-bis(arylseleninyl)-1-alkenes is induced by the SeO interaction, whereas the sulfur analogs lacks this type of nonbonding interaction.
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Synthesis of multiply substituted 1,6-dihydropyridines through Cu(I)-catalyzed 6-endo cyclization

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5955-5963
DOI: 10.1039/C5OB00356C, PaperHaruki Mizoguchi, Ryo Watanabe, Shintaro Minami, Hideaki Oikawa, Hiroki Oguri
Copper-catalyzed 6-endo cyclization of N-propargylic [small beta]-enaminocarbonyls was developed for the synthesis of oxidation-labile 1,6-dihydropyridines.
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An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5859-5861
DOI: 10.1039/C5OB00494B, CommunicationRoomi Mohima Chowdhury, Jonathan D. Wilden
A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N[prime or minute]-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.
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Targeting intracellular bacteria with an extended cationic amphiphilic polyproline helix

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5930-5936
DOI: 10.1039/C5OB00227C, PaperManish Nepal, Shankar Thangamani, Mohamed N. Seleem, Jean Chmielewski
Eradicating pathogenic bacteria that reside within mammalian cells is currently quite difficult. Herein we describe an agent with the dual properties of efficient mammalian cell penetration and potent antibacterial activity. Significantly, these activities can be combined to target pathogenic bacteria within macrophages.
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Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to [small alpha],[small beta]-unsaturated nitriles

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5918-5923
DOI: 10.1039/C5OB00394F, PaperBrij Bhushan Ahuja, Arumugam Sudalai
An efficient catalytic route for the synthesis of [small alpha],[small beta]-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed.
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Rhenium-catalyzed dehydrogenative olefination of C(sp3)-H bonds with hypervalent iodine(III) reagents

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5880-5884
DOI: 10.1039/C5OB00619H, CommunicationHaidong Gu, Congyang Wang
A dehydrogenative olefination of C(sp3)-H bonds is developed by merging rhenium catalysis with an alanine-derived hypervalent iodine(III) reagent.
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A lactone-fused cyclohexadiene as a versatile platform for diversified synthesis of 5,6,5-tricyclic scaffolds

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5862-5866
DOI: 10.1039/C5OB00729A, CommunicationM. Shibuya, T. Sudoh, T. Kawamura, Y. Yamamoto
A new lactone-fused cyclohexadiene platform for the stereoselective synthesis of differently functionalized 5,6,5-tricyclic scaffolds.
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Gold-catalyzed cascade C-H/C-H cross-coupling/cyclization/alkynylation: an efficient access to 3-alkynylpyrroles

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5867-5870
DOI: 10.1039/C5OB00599J, CommunicationShuai Zhang, Yuanhong Ma, Jingbo Lan, Feijie Song, Jingsong You
An efficient approach to 3-alkynylpyrroles has been developed through the gold-catalyzed cascade oxidative C-H/C-H cross-coupling, cyclization and in situ oxidative alkynylation.
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The synthesis of new amphiphilic p-tert-butylthiacalix[4]arenes containing peptide fragments and their interaction with DNA

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5894-5904
DOI: 10.1039/C5OB00548E, PaperPavel L. Padnya, Elena A. Andreyko, Olga A. Mostovaya, Ildar Kh. Rizvanov, Ivan I. Stoikov
The synthesis of new amphiphilic p-tert-butylthiacalix[4]arenes containing peptide fragments and their interaction with DNA is reported.
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77Se and 125Te NMR spectroscopy on a selectivity study of organochalcogenanes with L-amino acids

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5924-5929
DOI: 10.1039/C5OB00373C, PaperMarcio S. Silva, Leandro H. Andrade
Organochalcogenanes exhibited a remarkably high selectivity for L-cysteine which was monitored by 77Se and 125Te NMR spectroscopy.
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Copper(II)-catalyzed highly regio- and stereo-selective hydrosilylation of unactivated internal alkynes with silylborate in water

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5871-5874
DOI: 10.1039/C5OB00694E, CommunicationQing-Qing Xuan, Chuan-Li Ren, Li Liu, Dong Wang, Chao-Jun Li
The hydrosilylation of internal alkynes with Me2PhSiBpin catalyzed by Cu(OTf)2 in water provided multisubstituted vinylsilanes in high regio- and stereoselectivities.
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