Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2393-2398
DOI: 10.1039/C4OB02046D, PaperYahya E. Jad, Gerardo A. Acosta, Sherine N. Khattab, Beatriz G. de la Torre, Thavendran Govender, Hendrik G. Kruger, Ayman El-Faham, Fernando Albericio
To date, DMF has been considered as the only solvent suitable for peptide synthesis.
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[small alpha]-Tocopherol derived lipid dimers as efficient gene transfection agents. Mechanistic insights into lipoplex internalization and therapeutic induction of apoptotic activity

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2444-2452
DOI: 10.1039/C4OB02063D, PaperKrishan Kumar, Bappa Maiti, Paturu Kondaiah, Santanu Bhattacharya
Dimeric cationic tocopheryl lipids for efficacious therapeutic pDNA delivery in cancer cell lines.
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Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2247-2250
DOI: 10.1039/C4OB02602K, CommunicationAlafate Adili, Zhong-Lin Tao, Dian-Feng Chen, Zhi-Yong Han
2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities.
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Tetrahydrofuranyl and tetrahydropyranyl protection of amino acid side-chains enables synthesis of a hydroxamate-containing aminoacylated tRNA

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2341-2349
DOI: 10.1039/C4OB02212B, PaperLester J. Lambert, Marvin J. Miller, Paul W. Huber
O-protection using tetrahydrofuranyl or tetrahydropyranyl enabled addition of a hydroxamate-containing unnatural amino acid to a suppressor tRNA, allowing subsequent site-specific incorporation of the amino acid into the transcription factor, TFIIIA.
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Enantioselective carbolithiation of S-alkenyl-N-aryl thiocarbamates: kinetic and thermodynamic control

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2330-2340
DOI: 10.1039/C4OB02329C, PaperDaniele Castagnolo, Leonardo Degennaro, Renzo Luisi, Jonathan Clayden
Carbolithiation of vinyl thiocarbamates may proceed with the same sense of enantioselectivity with either (-)-sparteine and (+)-sparteine surrogate ligands.
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Formamidine hydrochloride as an amino surrogate: I2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N-H) [small alpha]-ketoamides

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2239-2242
DOI: 10.1039/C4OB02591A, CommunicationShan Liu, Qinghe Gao, Xia Wu, Jingjing Zhang, Kerong Ding, Anxin Wu
A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones has been developed. This reaction represents a novel strategy for the synthesis of free (N-H) [small alpha]-ketoamides.
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Byproduct promoted regioselective sulfenylation of indoles with sulfinic acids

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2251-2254
DOI: 10.1039/C4OB02575J, CommunicationCong-Rong Liu, Liang-Hui Ding
An unprecedented method to synthesise 3-sulfenylindoles is demonstrated via byproduct promoted sulfenylation of indoles with sulfinic acids.
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A novel enantioselective synthesis of 6H-dibenzopyran derivatives by combined palladium/norbornene and cinchona alkaloid catalysis

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2260-2263
DOI: 10.1039/C4OB02551B, CommunicationDi Xu, Li Dai, Marta Catellani, Elena Motti, Nicola Della Ca', Zhiming Zhou
Chiral dibenzopyran derivatives were obtained by cinchona alkaloid, as organocatalyst, in combination, for the first time, with palladium/norbornene catalytic system.
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Pd-catalyzed benzylic C-H oxidation of cyclotriveratrylene - product diversity

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2323-2329
DOI: 10.1039/C4OB02469A, PaperB. Senthilkumar, R. G. Gonnade, C. V. Ramana
The inner-rim oxidation of CTV has been explored with palladium and an interesting array of CTV derivatives has been obtained by simple changes in the solvent/conditions employed.
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The effect of leaving radical on the formation of tetrahydroselenophene by SHi ring closure: an experimental and computational study

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2310-2316
DOI: 10.1039/C4OB02434F, PaperAmber N. Hancock, Sofia Lobachevsky, Naomi L. Haworth, Michelle L. Coote, Carl H. Schiesser
Competition kinetic studies augmented with laser-flash photolysis and high-level computational techniques [G3(MP2)-RAD], with [COSMO-RS, SMD] and without solvent correction, provide kinetic parameters for the ring closures of a series of 4-(alkylseleno)butyl radicals.
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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

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2285-2292
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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Mixed alkyl aryl phosphonate esters as quenched fluorescent activity-based probes for serine proteases

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2293-2299
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

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2317-2322
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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A supramolecular topical gel derived from a non-steroidal anti-inflammatory drug, fenoprofen, is capable of treating skin inflammation in mice

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2300-2309
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

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2437-2443
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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Styryl ether formation from benzyl alcohols under transition-metal-free basic DMSO conditions

16 February, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,2267-2272
DOI: 10.1039/C4OB02358G, PaperKai Yang, Qiuling Song
A phenol-catalyzed aerobic oxidative styryl ether formation method was developed with benzyl alcohol under basic DMSO.
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Correction: Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

12 February, 2015 - 13:17
Org. Biomol. Chem., 2015, 13,2196-2196
DOI: 10.1039/C5OB90015H, CorrectionRui Wang, Anyu He, Errabelli Ramu, John R. Falck
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Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity

12 February, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,1996-2000
DOI: 10.1039/C4OB02561J, CommunicationTarun Kumar, Deepti Verma, Rubem F. S. Menna-Barreto, Wagner O. Valenca, Eufranio N. da Silva Junior, Irishi N. N. Namboothiri
Functionalized imidazoles derived from nitroallylic acetates and amidines exhibit potent activity against T. cruzi, the etiological agent of Chagas disease.
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Synthesis of a novel water-soluble cylindrical macrotricyclic host and its complexation with N-methylquinolinium and N-methylisoquinolinium salts: formation of 1 : 2 complexes in water

12 February, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,1988-1991
DOI: 10.1039/C4OB02533D, CommunicationFei Zeng, Chuan-Feng Chen
A water-soluble cylindrical macrotricyclic host could form 1 : 2 complexes with N-methylquinolinium or N-methylisoquinolinium salts in water solution and in the solid state.
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Highly efficient synthesis of novel methyl 132-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction

12 February, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,1992-1995
DOI: 10.1039/C4OB02491E, CommunicationJiazhu Li, Yang Liu, Xi-Sen Xu, Yan-Long Li, Shan-Guo Zhang, Il Yoon, Young Key Shim, Jin-Jun Wang, Jun-Gang Yin
pH-Dependent regioselective condensation of methyl mesopyropheophorbide a with HCHO is studied and stereoselective Michael reaction of the 132-methylene product is also discussed.
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