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Contents list for Organic & Biomolecular Chemistry, issue 22, 2009
Front cover
Org. Biomol. Chem., 2009, 7, 4549
DOI: 10.1039/b921540a
Inside front cover
Org. Biomol. Chem., 2009, 7, 4550
DOI: 10.1039/b921542p
Contents and Chemical Science
Org. Biomol. Chem., 2009, 7, 4551
DOI: 10.1039/b921543n
Perspective
1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents
Carmen Nájera and José M. Sansano,
Org. Biomol. Chem., 2009, 7, 4567
DOI: 10.1039/b913066g
In this perspective the most important virus inhibitors generated by 1,3-dipolar cycloadditions are described.
Communications
Efficient synthesis of the C7-C20 subunit of amphidinolides C and F
Subham Mahapatra and Rich G. Carter,
Org. Biomol. Chem., 2009, 7, 4582
DOI: 10.1039/b916744g
Features of this work include a diastereoselective allylic epoxide ring opening, an organolithium coupling/olefination sequence to construct the diene moiety and a sulfone alkylation/hydroxylation coupling strategy.
Olefin metathesis in carotenoid synthesis
Takayuki Kajikawa, Naoko Iguchi and Shigeo Katsumura,
Org. Biomol. Chem., 2009, 7, 4586
DOI: 10.1039/b915390j
We attempted to apply olefin metathesis to the synthesis of symmetrical carotenoids. In this paper, the syntheses of violaxanthin and mimulaxanthin are described using the olefin metathesis protocol.
Fluorescent detection of methylmercury by desulfurization reaction of rhodamine hydrazide derivatives
Young-Keun Yang, Sung-Kyun Ko, Injae Shin and Jinsung Tae,
Org. Biomol. Chem., 2009, 7, 4590
DOI: 10.1039/b915723a
Irreversible chemosensors based on rhodamine thiosemicarbazide can visualize methylmercury species in live cells and zebrafish.
Synthesis of acetal protected building blocks using flow chemistry with flow I.R. analysis: preparation of butane-2,3-diacetal tartrates
Catherine F. Carter, Ian R. Baxendale, Matthew O'Brien, John B. J. Pavey and Steven V. Ley,
Org. Biomol. Chem., 2009, 7, 4594
DOI: 10.1039/b917289k
The syntheses of butane-2,3-diacetal (BDA) protected tartrate derivatives are described using continuous flow processing techniques with in-line purification and I.R. analytical protocols.
Papers
Sensing of peptide hormones with dynamic combinatorial libraries of metal–dye complexes: the advantage of time-resolved measurements
Friederike Zaubitzer, Thomas Riis-Johannessen and Kay Severin,
Org. Biomol. Chem., 2009, 7, 4598
DOI: 10.1039/b912400d
A mixture of three dyes and two transition metal salts was used to sense low millimolar concentrations of the peptide hormones angiotensin I and angiotensin II.
Biocatalytic oxidation by chloroperoxidase from Caldariomyces fumago in polymersome nanoreactors
H. M. de Hoog, M. Nallani, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte and I. W. C. E. Arends,
Org. Biomol. Chem., 2009, 7, 4604
DOI: 10.1039/b911370c
The functional encapsulation of chloroperoxidase into PS-PIAT polymersomes is reported as well as the catalytic behaviour of the encapsulated biocatalyst in the oxidaton of (R)-phenyl methyl sulfoxide, a chiral intermediate.
Magnesium-mediated intramolecular reductive coupling: a stereoselective synthesis of C2-symmetric 3,4-bis-silyl-substituted adipic acid derivatives
Pintu K. Kundu and Sunil K. Ghosh,
Org. Biomol. Chem., 2009, 7, 4611
DOI: 10.1039/b910784c
A symmetrical disiloxane made using a chiral N-
-silylacryloyloxazolidinone underwent a Mg/Me3SiCl mediated reductive cyclisation to provide synthetically useful C2-symmetric trans-diastereoisomers with high selectivity. The individual trans-diastereoisomers were easily separated by fractional crystallisation with high recoveries.
Design of a -hairpin peptide-intercalator conjugate for simultaneous recognition of single stranded and double stranded regions of RNA
Lauren L. Cline and Marcey L. Waters,
Org. Biomol. Chem., 2009, 7, 4622
DOI: 10.1039/b913024a
By conjugating two weak RNA ligands with selectivities for different aspects of RNA structure (stem and bulge), we have designed a ligand with enhanced binding affinity and selectivity.
Complexes in benzidine rearrangement
Shinichi Yamabe, Hazuki Nakata and Shoko Yamazaki,
Org. Biomol. Chem., 2009, 7, 4631
DOI: 10.1039/b909313c
Benzidine rearrangement was studied by DFT calculation. The intermediate proposed by Dewar was not found for the parent hydrazobenzene, but was found for dimethoxyhydrazobenzene.
Synthesis of functionalized H-pyrazolo[5,1-a]isoquinolines via sequential reactions of N
-(2-alkynylbenzylidene)hydrazides
Zhiyuan Chen, Mingchao Su, Xingxin Yu and Jie Wu,
Org. Biomol. Chem., 2009, 7, 4641
DOI: 10.1039/b914265g
Diversity-oriented synthesis of functionalized H-pyrazolo[5,1-a]isoquinolines via sequential reactions of N-(2-alkynylbenzylidene)hydrazide is described.
Ionic liquid: an efficient and recyclable medium for synthesis of unsymmetrical diorganyl selenides promoted by InI
Senthil Narayanaperumal, Eduardo E. Alberto, Fabiano Molinos de Andrade, Eder J. Lenardão, Paulo S. Taube and Antonio L. Braga,
Org. Biomol. Chem., 2009, 7, 4647
DOI: 10.1039/b910699e
In an environmental friendly protocol, InI was used as a reducing agent for the Se–Se bond to prepare unsymmetrical diorganyl selenides with very short reaction times, mild conditions and excellent yields using (bmim)BF4 as a recyclable solvent.
Conjugation of substituted naphthalimides to polyamines as cytotoxic agents targeting the Akt/mTOR signal pathway
Zhi-yong Tian, Song-qiang Xie, Zi-hou Mei, Jin Zhao, Wen-yuan Gao and Chao-jie Wang,
Org. Biomol. Chem., 2009, 7, 4651
DOI: 10.1039/b912685f
A series of naphthalimide polyamine conjugates, designed to harness the polyamine transporter for drug delivery, produce antitumor effects through apoptosis and cell cycle arrest with Akt/mTOR signal pathway as upstream cellular target. The presence of DFMO or spermidine only either elevated or attenuated the effects.
Selective recognition of tetrahedral dianions by a hexaaza cryptand receptor
Pedro Mateus, Rita Delgado, Paula Brandão, Sílvia Carvalho and Vítor Félix,
Org. Biomol. Chem., 2009, 7, 4661
DOI: 10.1039/b912940e
The studied protonated hexaaza cryptand was revealed to be selective for tetrahedral dianions over mononegative ones. The crystal structure of the sulfate cryptate showed the anion held inside the cavity.
Ni and Pd mediate asymmetric organoboron synthesis with ester functionality at the -position
Vanesa Lillo, Michael J. Geier, Stephen A. Westcott and Elena Fernández,
Org. Biomol. Chem., 2009, 7, 4674
DOI: 10.1039/b909341a
Catalytic systems based on Ni and Pd complexes modified with chiral P-P ligands can be used in a convenient strategy for enantioselectively adding a boron unit to the -position of 
,-unsaturated esters. Both Ni(0) and Ni(II) have promoted the highest asymmetric induction so far reported for the boron addition reaction, with values up to 98% e.e., when (R)-(S)-Taniaphos was used as the chiral ligand.
Cation localization and movement within DNA thrombin binding aptamer in solution
Marko Trajkovski, Primo
ket and Janez Plavec,
Org. Biomol. Chem., 2009, 7, 4677
DOI: 10.1039/b914783g
Solution-state NMR was used to localize 15NH4+ ions between the two G-quartets of TBA, determine the binding constant and study dynamics of 15NH4+ ion movement.
CCMV capsid formation induced by a functional negatively charged polymer
Inge J. Minten, Yujie Ma, Mark A Hempenius, G. Julius Vancso, Roeland J. M. Nolte and Jeroen J. L. M. Cornelissen,
Org. Biomol. Chem., 2009, 7, 4685
DOI: 10.1039/b915028e
A functional negatively charged polyelectrolyte, polyferrocenylsilane (PFS) was encapsulated in cowpea chlorotic mottle virus (CCMV) capsid proteins, yielding monodisperse particles of 18 nm in size with altered redox properties compared to the parent materials.
Development of highly sensitive and selective molecules for detection of spermidine and spermine
Daisuke Tanima, Yoko Imamura, Takeo Kawabata and Kazunori Tsubaki,
Org. Biomol. Chem., 2009, 7, 4689
DOI: 10.1039/b909682e
To establish an effective and concise procedure for determining the concentrations of spermidine and spermine, several functional molecules based on phenolphthalein and two crown loops were constructed.
Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists
Michael P. Van Ryssen, Nicolaos Avlonitis, Rashid Giniatullin, Craig McDougall, James L. Carr, Megan N. Stanton-Humphreys, Emma L. A. Borgström, C. Tom A. Brown, Dmitriy Fayuk, Alexander Surin, Minna Niittykoski, Leonard Khiroug and Stuart J. Conway,
Org. Biomol. Chem., 2009, 7, 4695
DOI: 10.1039/b914981c
The synthesis of eight caged TRPV1 agonists and antagonists is reported. Photolysis of a caged agonist in trigeminal neurons leads to activation of TRPV1 in vitro.
The reaction of acyl cyanides with 
Huisgen zwitterion
: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms
Xu-Guang Liu, Yin Wei and Min Shi,
Org. Biomol. Chem., 2009, 7, 4708
DOI: 10.1039/b913196e
The rearrangement reaction of acyl cyanides and Huisgen zwitterions, affords hydrazone derivatives at high temperature and azine derivatives at low temperature, respectively.
Phenylenediamine-based bivalent glycocyclophanes: synthesis and analysis of the influence of scaffold rigidity and ligand spacing on lectin binding in cell systems with different glycomic profiles
Sabine André, Trinidad Velasco-Torrijos, Rosaria Leyden, Sebastien Gouin, Manuela Tosin, Paul V. Murphy and Hans-Joachim Gabius,
Org. Biomol. Chem., 2009, 7, 4715
DOI: 10.1039/b913010a
A panel of bivalent compounds is synthesised and used to establish the influence of scaffold flexibility on inhibitory potency in a medically relevant test system.
N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates
Katsuhiko Suzuki, Akifumi Tobe, Shin Adachi, Shusaku Daikoku, Yasuko Hasegawa, Yuki Shioiri, Mariko Kobayashi and Osamu Kanie,
Org. Biomol. Chem., 2009, 7, 4726
DOI: 10.1039/b909556j
The potential applications of N-hexyl-4-aminobutyl glycosides in the mass spectrometric investigation of glycan structure and in the investigation of glycan functions were studied. The usefulness of N-hexyl-4-aminobutyl glycosides in biological analysis was also confirmed.
Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies
Oliver Plietzsch, Christine Inge Schilling, Mariyan Tolev, Martin Nieger, Clemens Richert, Thierry Muller and Stefan Bräse,
Org. Biomol. Chem., 2009, 7, 4734
DOI: 10.1039/b912189g
A modular concept for the generation of tetrahedral tectons from common precursors was developed. Tetraphenylmethane or 1,3,5,7-tetraphenyladamantane based cores structures are obtained through high-yielding four-fold click reactions, using either the tetraazido or the tetraalkyne precursors.
Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles
Hyun-Suk Yeom, Youngun Lee, Ji-Eun Lee and Seunghoon Shin,
Org. Biomol. Chem., 2009, 7, 4744
DOI: 10.1039/b910757f
We report geometry-dependent cyclizations of o-alkynylaryl ketoximes and nitrones catalyzed by gold complexes.
Exploring synthetic avenues for the effective synthesis of selenium- and tellurium-containing multifunctional redox agents
Susanne Mecklenburg, Saad Shaaban, Lalla A. Ba, Torsten Burkholz, Thomas Schneider, Britta Diesel, Alexandra K. Kiemer, Anne Röseler, Katja Becker, Jörg Reichrath, Alexandra Stark, Wolfgang Tilgen, Muhammad Abbas, Ludger A. Wessjohann, Florenz Sasse and Claus Jacob,
Org. Biomol. Chem., 2009, 7, 4753
DOI: 10.1039/b907831b
Aminoalkylation, amide coupling and multicomponent reactions allow the effective synthesis of multifunctional agents that contain selenium and tellurium and are biologically active against a range of targets, including human cancer cell lines, dermatophytes and Plasmodium falciparum.
Synthetic dinucleotide mRNA cap analogs with tetraphosphate 5,5 bridge containing methylenebis(phosphonate) modification
Anna Maria Rydzik, Maciej Lukaszewicz, Joanna Zuberek, Joanna Kowalska, Zbigniew Marek Darzynkiewicz, Edward Darzynkiewicz and Jacek Jemielity,
Org. Biomol. Chem., 2009, 7, 4763
DOI: 10.1039/b911347a
The synthesis of cap analogs modified with a methylene group in the tetraphosphate bridge is presented. The compounds are potent inhibitors of translation in vitro with increased enzymatic stability and have high affinity for eIF4E protein.
Rediscovering copper-based catalysts for intramolecular carbon–hydrogen bond functionalization by carbene insertion
Carmen Martín, Tomás R. Belderraín and Pedro J. Pérez,
Org. Biomol. Chem., 2009, 7, 4777
DOI: 10.1039/b911589g
TpxCu complexes catalyze the functionalization of C–H bonds by means of an intramolecular carbene insertion process, which affords lactones or lactams in yields comparable with or better than those already reported for rhodium catalysts.
Direct metallation of thienopyrimidines using a mixed lithium–cadmium base and antitumor activity of functionalized derivatives
Katia Snégaroff, Frédéric Lassagne, Ghenia Bentabed-Ababsa, Ekhlass Nassar, Sidaty Cheikh Sid Ely, Stéphanie Hesse, Enrico Perspicace, Aïcha Derdour and Florence Mongin,
Org. Biomol. Chem., 2009, 7, 4782
DOI: 10.1039/b915274a
Thieno[2,3-d]- and thieno[3,2-d]pyrimidines have been synthesized using as key step a deproto-cadmiation–trapping sequence.
Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF5
Fei Liu, Agnès Martin-Mingot, Marie-Paule Jouannetaud, Omar Karam and Sébastien Thibaudeau,
Org. Biomol. Chem., 2009, 7, 4789
DOI: 10.1039/b915077c
The hydrofluorination and novel homodimerization/fluorination reactions, involving ammonium–carbenium superelectrophiles in superacid HF/SbF5, were studied and applied to the synthesis of highly valued fluorinated nitrogen-containing building blocks.
Back matter
Org. Biomol. Chem., 2009, 7, 4798
DOI: 10.1039/b921551b
Back cover
Org. Biomol. Chem., 2009, 7, 4799
DOI: 10.1039/b921552m
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