Royal Society of Chemistry

Linear versus branched poly-lysine/arginine as polarity enhancer tags

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7194-7196
DOI: 10.1039/C4OB01354A, CommunicationMarta Paradis-Bas, Maria Albert-Soriano, Judit Tulla-Puche, Fernando Albericio
The design and synthesis of Lys- and Arg-containing peptides as solubilizing tags were studied to evaluate their influence on polarity.
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Linear synthesis of the branched pentasaccharide repeats of O-antigens from Shigella flexneri 1a and 1b demonstrating the major steric hindrance associated with type-specific glucosylation

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01200C, PaperJason M. Hargreaves, Yann Le Guen, Catherine Guerreiro, Karine Descroix, Laurence A. Mulard
Shigella flexneri serotypes 1b and 1a are Gram-negative enteroinvasive bacteria causing shigellosis in humans.
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Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00677A, PaperQing-Han Li, Jung-Wei Liao, Yi-Ling Huang, Ruei-Tang Chiang, Han-Mou Gau
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported.
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A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7381-7388
DOI: 10.1039/C4OB00642A, PaperXiaofeng Ma, Qin Tang, Jun Ke, Jichao Zhang, Xinglong Yang, Xudong Shen, Huawu Shao
A highly diastereoselective synthesis method for 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives from 2-C-branched sugars via a neighboring group participation strategy was developed.
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Synthesis of a chiral building block for highly functionalized polycyclic ethers

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01439A, PaperG. Pazos, M. Perez, Z. Gandara, G. Gomez, Y. Fall
An efficient procedure for preparing enantiopure polycyclic ethers based on the furan singlet oxygen oxidation approach is reported.
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A versatile strategy for appending a single functional group to a multifunctional host through host-guest covalent-capture

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01429D, PaperJean-Noel Rebilly, Assia Hessani, Benoit Colasson, Olivia Reinaud
A novel two-step strategy allowed us to selectively monofunctionalize a molecular host (calix[6]arene) with various groups of interest (redox tag, fluorophore, chelating ligand).
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Cooperative hybridization of [gamma]PNA miniprobes to a repeating sequence motif and application to telomere analysis

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7345-7354
DOI: 10.1039/C4OB00953C, PaperHa H. Pham, Connor T. Murphy, Gopalsamy Sureshkumar, Danith H. Ly, Patricia L. Opresko, Bruce A. Armitage
High affinity [gamma]PNA oligomers hybridize cooperatively on telomeric DNA and provide bright fluorescent signals.
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First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7338-7344
DOI: 10.1039/C4OB01470G, PaperChaolei Wang, Guoxiang Wei, Xue Yang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu
The first total synthesis of S-(+)-XJP and R-(-)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.
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68Ga based probe for Alzheimer's disease: synthesis and preclinical evaluation of homodimeric chalcone in [small beta]-amyloid imaging

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7328-7337
DOI: 10.1039/C4OB00941J, PaperKanchan Chauhan, Anupama Datta, Anupriya Adhikari, Krishna Chuttani, Ajai Kumar Singh, Anil K. Mishra
68Ga complex of chalcone-based bivalent ligand as a potential candidate for cost-effective PET imaging of Alzheimer's disease: a new perspective.
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Facile synthesis of 5-hydroxy-L-lysine from D-galactose as a chiral-precursor

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7310-7317
DOI: 10.1039/C4OB01220H, PaperLina Guo, Taibao Liu, Kai Chen, Tianbang Song, Peng George Wang, Wei Zhao
A concise synthesis of (2S,5R) and (2S,5S)-5-hydroxy-lysine was achieved by utilizing D-galactose as a chiral-precursor with stereo retention. Using the diazido intermediate, the derived [small beta]-D-galactopyranosyl and [small alpha]-D-glucopyranosyl-(1[rightward arrow]2)-[small beta]-D-galactosyl moieties were synthesized.
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Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7257-7260
DOI: 10.1039/C4OB01188K, PaperB. V. Subba Reddy, S. Gopal Reddy, M. Ramana Reddy, Manika Pal Bhadra, A. V. S. Sarma
A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a Prins/pinacol cascade.
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Benzodithiophene based [small pi]-conjugated macrocycles: synthesis, morphology and electrochemical characterization

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7375-7380
DOI: 10.1039/C4OB01043D, PaperAnjan Bedi, Sanjio S. Zade
A 7,8-didodecyloxybenzo[1,2-b:4,3-b[prime or minute]]dithiophene (BdT-Dod) containing a macrocycle was constructed from a thiophene capped BdT-Dod comonomer through a Ti(IV) mediated McMurry reaction. The macrocycle exhibited self-aggregation in the solid state to form microfibers of a thickness of [similar]400 nm.
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Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7355-7365
DOI: 10.1039/C4OB00735B, PaperJan-Hendrik Lamm, Johanna Glatthor, Jan-Henrik Weddeling, Andreas Mix, Jasmin Chmiel, Beate Neumann, Hans-Georg Stammler, Norbert W. Mitzel
A series of 1,5-, 1,8-, 9,10- and 1,8,10-alkynyl-substituted anthracenes have been synthesised. Amongst others, 9,10-bis[(trimethylsilyl)ethynyl]anthracene was photo-dimerised. The photodimer is thermally unstable as was investigated by VT NMR spectroscopy.
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Total syntheses and structural validation of lincitol A, lincitol B, uvacalol I, uvacalol J, and uvacalol K

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7279-7289
DOI: 10.1039/C4OB01329H, PaperSoumik Mondal, Kana M. Sureshan
First total syntheses of lincitol A, lincitol B, uvacalol I, uvacalol J and uvacalol K were achieved in racemic form, validating their structure from a common intermediate, which was synthesized in six steps from low-cost and extensively available myo-inositol.
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The effect of LNA nucleobases as enhancers for the binding of amiloride to an abasic site in DNA/DNA and DNA/RNA duplexes

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7250-7256
DOI: 10.1039/C4OB00977K, PaperYusuke Sato, Tetsushi Sato, Takaya Sato, Seiichi Nishizawa, Norio Teramae
We report on a significant effect of locked nucleic acid (LNA) nucleobases on the binding of amiloride for abasic site (AP)-containing DNA duplexes.
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Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkers

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7238-7249
DOI: 10.1039/C4OB01281J, PaperAnand D. Tiwari, Siva S. Panda, Adel S. Girgis, Sandhyamayee Sahu, Riham F. George, Aladdin M. Srour, Brian La Starza, Abdullah M. Asiri, C. Dennis Hall, Alan R. Katritzky
Twelve novel conjugates of NSAID linked by amino acid units to acetaminophen synthesized under microwave irradiation as potential anti-inflammatory agents.
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Recent advances in catalytic C-N bond formation: a comparison of cascade hydroaminomethylation and reductive amination reactions with the corresponding hydroamidomethylation and reductive amidation reactions

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7179-7193
DOI: 10.1039/C4OB00620H, Review ArticleSaeed Raoufmoghaddam
This review highlights and compares selected examples of hydroaminomethylation, reductive amination, hydroamidomethylation and reductive amidation reactions, and consequently reveals their potential applications.
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Palladium-catalyzed carbonylative addition of aryl bromides to arylalkynes: a simple and efficient method for chalcone synthesis

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7233-7237
DOI: 10.1039/C4OB01263A, PaperSheng Zhang, Liangguang Wang, Xiujuan Feng, Ming Bao
Chalcones can be prepared in satisfactory to excellent yields via palladium-catalyzed carbonylative addition of aryl bromides to terminal arylalkynes under mild conditions.
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Synthesis and immunological effects of heroin vaccines

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7211-7232
DOI: 10.1039/C4OB01053A, PaperFuying Li, Kejun Cheng, Joshua F. G. Antoline, Malliga R. Iyer, Gary R. Matyas, Oscar B. Torres, Rashmi Jalah, Zoltan Beck, Carl R. Alving, Damon A. Parrish, Jeffrey R. Deschamps, Arthur E. Jacobson, Kenner C. Rice
Multi-step syntheses provided three designed haptens for vaccines that were evaluated for their ability to block the effects of heroin and its metabolites.
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Ionic liquids as porogens for molecularly imprinted polymers: propranolol, a model study

Org. and Biomol. Chem. - 1 September, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,7201-7210
DOI: 10.1039/C4OB00547C, PaperKatherine Booker, Clovia I. Holdsworth, Cara M. Doherty, Anita J. Hill, Michael C. Bowyer, Adam McCluskey
The selectivity and rebinding capacity of molecularly imprinted polymers selective for propranolol (1) using the room temperature ionic liquids [BMIM][BF4], [BMIM][PF6], [HMIM][PF6] and [OMIM][PF6] and CHCl3 were examined.
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