Org. and Biomol. Chem.

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Selective transamidation of 3-oxo-N-acyl homoserine lactones by hydrazine derivatives

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7197-7200
DOI: 10.1039/C4OB01156B, CommunicationMichael A. Bertucci, Stephen J. Lee, Michel R. Gagne
Hydrazine derivatives are employed for selective amide cleavage of 3-oxo-N-acyl homoserine lactones under physiologically relevant conditions.
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A computational study of the activation of allenoates by Lewis bases and the reactivity of intermediate adducts

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7297-7309
DOI: 10.1039/C4OB01177E, PaperGou-Tao Huang, Timm Lankau, Chin-Hui Yu
Several chemical properties of Lewis base-allenoate adducts (LB[middle dot]allenoate), such as solvent effect, basicity, nucleophilicity and cycloaddition, are studied to provide a detailed foundation for the analysis of LB-catalyzed reactions of allenoates.
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Next generation maleimides enable the controlled assembly of antibody-drug conjugates via native disulfide bond bridging

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7261-7269
DOI: 10.1039/C4OB01550A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Felix F. Schumacher, Joao P. M. Nunes, Antoine Maruani, Vijay Chudasama, Mark E. B. Smith, Kerry A. Chester, James R. Baker, Stephen Caddick
Highly homogeneous ADCs are generated by the efficient bridging of interchain disulfide bonds in trastuzumab, using next generation maleimides.
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A hydrazide-anchored dendron scaffold for chemoselective ligation strategies

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7290-7296
DOI: 10.1039/C4OB00870G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Liz O'Donovan, Paul A. De Bank
We report the design and synthesis of a dendron scaffold, enabling the chemoselective decoration of target molecules with multiple copies of functional species, such as peptides, via a hydrazone bond.
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Iridium-catalyzed C-H borylation of pyridines

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7318-7327
DOI: 10.1039/C4OB01565G, PaperScott A. Sadler, Hazmi Tajuddin, Ibraheem A. I. Mkhalid, Andrei S. Batsanov, David Albesa-Jove, Man Sing Cheung, Aoife C. Maxwell, Lena Shukla, Bryan Roberts, David C. Blakemore, Zhenyang Lin, Todd B. Marder, Patrick G. Steel
Iridium-catalysed C-H borylation is an efficient method for the preparation of pyridyl and related azinyl boronate esters.
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Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7270-7278
DOI: 10.1039/C4OB00734D, PaperB. Lygo, M. J. Palframan, G. Pattenden
DFT calculations probing potential cycloaddition pathways leading to the polycyclic ring systems found in the coral secondary metabolites plumarellide, mandapamate and rameswaralide are described.
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Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one ([small beta]-lactam), involving a cascade sequence of reactions as a key step

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7389-7396
DOI: 10.1039/C4OB00948G, PaperDipak Kumar Tiwari, Kishor Chandra Bharadwaj, Vedavati G. Puranik, Dharmendra Kumar Tiwari
A divergent, short, and novel total synthesis of 1,6,8a-tri-epi-castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed.
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Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates

9 September, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,7397-7409
DOI: 10.1039/C4OB01387E, PaperSantosh J. Gharpure, V. Prasath
C-fused pyranoheterocycles can be assembled in a highly diastereoselective manner using an intramolecular oxa-Pictet-Spengler type reaction of vinylogous carbonates.
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Linear versus branched poly-lysine/arginine as polarity enhancer tags

9 September, 2014 - 23:17

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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A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives

9 September, 2014 - 23:17

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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Cooperative hybridization of [gamma]PNA miniprobes to a repeating sequence motif and application to telomere analysis

9 September, 2014 - 23:17

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

9 September, 2014 - 23:17

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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

7 September, 2014 - 22:54

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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