Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3976-3985
DOI: 10.1039/C4OB00639A, PaperSaurav Bera, Gautam Panda
Practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived intermediates is described.
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Fast imine equilibration and its consequences for the evaluation of dynamic combinatorial libraries

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3827-3830
DOI: 10.1039/C4OB00507D, CommunicationK. Ziach, A. Kulesza, J. Jurczak
An example of the interplay between the templation and a very fast reequilibration of a DCL of imines that occurs upon a solvent change is reported. Such seemingly "irrelevant" details of the procedure like imine dissolution time may dictate the outcome of the whole reaction.
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Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of [small beta]-urea glycosides in aqueous solution

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3924-3931
DOI: 10.1039/C3OB42452A, PaperYoshiyasu Ichikawa, Takahiro Minami, Shohei Kusaba, Nobuyoshi Saeki, Yuta Tonegawa, Yumiko Tomita, Keiji Nakano, Hiyoshizo Kotsuki, Toshiya Masuda
The one step process, involving reactions between urea and protecting group free D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding [small beta]-urea glycosides.
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PEGylated meso-arylporpholactone metal complexes as optical cyanide sensors in water

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3991-4001
DOI: 10.1039/C4OB00697F, PaperJill L. Worlinsky, Steven Halepas, Christian Bruckner
A number of water-soluble metal complexes of PEGylated meso-fluorophenylporpholactones display a specific optical response upon addition of cyanide.
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Degradation of [small alpha]-melanocyte-stimulating hormone photosensitized by pterin

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3877-3886
DOI: 10.1039/C4OB00434E, PaperCarolina Castano, Carolina Lorente, Nathalie Martins-Froment, Esther Oliveros, Andres H. Thomas
The reaction is initiated by an electron transfer and produces chemical changes in at least tryptophan and tyrosine residues.
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Convergent and enantioselective syntheses of cytosolic phospholipase A2[small alpha] inhibiting N-(1-indazol-1-ylpropan-2-yl)carbamates

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,4021-4030
DOI: 10.1039/C4OB00535J, PaperTom Sundermann, Martina Arnsmann, Julian Schwarzkopf, Walburga Hanekamp, Matthias Lehr
A convergent synthesis for 4 and enantioselective syntheses for (R)-4 and (S)-4 starting from a (R)-serine derived oxazolidine were developed.
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19F NMR spectroscopy monitors ligand binding to recombinantly fluorine-labelled b[prime or minute]x from human protein disulphide isomerase (hPDI)

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3808-3812
DOI: 10.1039/C4OB00699B, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Rose Curtis-Marof, Denisa Doko, Michelle L. Rowe, Kirsty L. Richards, Richard A. Williamson, Mark J. Howard
Fluoroindole recombinant protein labelling enables a 19F NMR study to observe protein-ligand binding and dissociation constant determination.
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Synthesis and properties of chemiluminescent acridinium ester labels with fluorous tags

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3887-3901
DOI: 10.1039/C4OB00456F, PaperAnand Natrajan, David Wen, David Sharpe
Acridinium dimethylphenyl esters are highly sensitive chemiluminescent labels that are used in clinical diagnostics.
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Synthesis of new asymmetric xanthene dyes via catalyst-free SNAr with sulfur nucleophiles

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3816-3820
DOI: 10.1039/C4OB00533C, CommunicationMichaela Kotaskova, Okan Osman Oglou, Mark Helm
An unusual SNAr with sulfur nucleophiles on electron rich aromatic xanthenes affords a new class of photostable asymmetric thioether xanthene dyes.
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Development of a traceable linker containing a thiol-responsive amino acid for the enrichment and selective labelling of target proteins

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3821-3826
DOI: 10.1039/C4OB00622D, CommunicationJun Yamamoto, Masaya Denda, Nami Maeda, Miku Kita, Chiaki Komiya, Tomohiro Tanaka, Wataru Nomura, Hirokazu Tamamura, Youichi Sato, Aiko Yamauchi, Akira Shigenaga, Akira Otaka
A traceable linker that is potentially applicable to identification of a target protein of interest was developed.
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First total syntheses of chrestifoline-B and (+/-)-chrestifoline-C, and improved synthetic routes to bismurrayafoline-A, bismurrayafolinol and chrestifoline-D

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3831-3835
DOI: 10.1039/C4OB00609G, CommunicationCarsten Borger, Arndt W. Schmidt, Hans-Joachim Knolker
We describe an efficient synthesis of the methylene-bridged biscarbazole alkaloids bismurrayafoline-A, bismurrayafolinol and chrestifoline B-D using an Ullmann-type coupling at the benzylic position.
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Synthesis of [small alpha],[small beta]-unsaturated amides and iminocoumarins from N,N-disulfonyl ynamides with aldehydes via the ketenimine intermediate

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3986-3990
DOI: 10.1039/C4OB00513A, PaperLian Yu, Jian Cao
A novel synthesis of [small alpha],[small beta]-unsaturated amides from N,N-disulfonyl ynamides with aldehydes was developed. By utilization of salicylaldehydes, a variety of substituted iminocoumarins were prepared.
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Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3802-3807
DOI: 10.1039/C4OB00578C, CommunicationXiuling Chen, Tieqiao Chen, Yongbo Zhou, Daoqing Han, Li-Biao Han, Shuang-Feng Yin
An efficient metal-free aerobic C-N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency. All of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles.
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Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3813-3815
DOI: 10.1039/C4OB00705K, CommunicationKazutada Ikeuchi, Ryosuke Fujii, Shimpei Sugiyama, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima, Jae-Hoon Choi, Tomohiro Suzuki, Hirokazu Kawagishi, Toshiyuki Kan
AHX derivatives and their probe molecules.
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Lewis acid-promoted cyclization/halogenation of allenyl ethenetricarboxylates and the corresponding amides: stereoselective synthesis of haloalkenyl five-membered heterocycles

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3964-3975
DOI: 10.1039/C4OB00233D, PaperYugo Fukushima, Shoko Yamazaki, Akiya Ogawa
Lewis acid-promoted intramolecular reactions of allenyl ethenetricarboxylates and the corresponding amides gave 3,4-trans haloalkenyl five-membered heterocycles stereoselectively. Transformations of the products utilizing the haloalkenyl functionality have been demonstrated.
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Selective synthesis of 4-(sulfonyl)-methyl-1H-pyrazoles and (E)-4,5-dihydro-1H-pyrazoles from N-allenic sulfonylhydrazones

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3797-3801
DOI: 10.1039/C4OB00550C, CommunicationYu Zhu, Jun-Jie Hong, Yun-Bin Zhou, Yu-Wei Xiao, Min Lin, Zhuang-Ping Zhan
Selective synthesis of 4-(sulfonyl)-methyl-1H-pyrazoles and (E)-4,5-dihydro-1H-pyrazoles from N-allenic sulfonylhydrazones with sulfonyl group migrations has been developed.
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Tuning the chiroptical and morphological properties of steroidal-porphyrin aggregates: a mechanistic, structural, and MM investigation

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3956-3963
DOI: 10.1039/C4OB00134F, PaperChiara Lorecchio, Mariano Venanzi, Claudia Mazzuca, Raffaella Lettieri, Antonio Palleschi, Thu Huong Nguyen Thi, Lenka Cardova, Pavel Drasar, Donato Monti
The morphology and the chirality of a steroid-functionalised porphyrin aggregate can be effectively tuned by the reaction conditions used.
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Regiocontrolled palladium-catalyzed and copper-mediated C-H bond functionalization of protected L-histidine

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3792-3796
DOI: 10.1039/C4OB00430B, CommunicationAmit Mahindra, Rahul Jain
Regiocontrolled transition-metal-catalyzed C-H bond arylation of protected L-histidine with aryl halides as the coupling partner is reported.
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A concise approach to polysubstituted oxazoles from N-acyl-2-bromo enamides via a copper(I)/amino acid-catalyzed intramolecular C-O bond formation

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3912-3923
DOI: 10.1039/C4OB00309H, PaperBingjie Liu, Yueteng Zhang, Gang Huang, Xinting Zhang, Pengfei Niu, Jie Wu, Wenquan Yu, Junbiao Chang
A straightforward and efficient copper(I)/amino acid-catalyzed intramolecular Ullmann-type C-O coupling reaction has been developed for oxazole synthesis.
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3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3950-3955
DOI: 10.1039/C4OB00280F, PaperDanzhu Wang, Weixuan Chen, Yueqin Zheng, Chaofeng Dai, Ke Wang, Bowen Ke, Binghe Wang
Over 14 000 fold rate difference for selective labeling was achieved by varying the substituents on tetrazines coupled with different dienophiles.
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