Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Diastereoselective Ireland-Claisen rearrangements of substituted allyl [small beta]-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

15 April, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,2702-2728
DOI: 10.1039/C4OB00274A, PaperStephen G. Davies, Ai M. Fletcher, James A. Lee, Paul M. Roberts, Myriam Y. Souleymanou, James E. Thomson, Charlotte M. Zammit
The Ireland-Claisen rearrangements of substituted allyl [small beta]-amino esters were evaluated, and subsequently employed in syntheses of C(5)-substituted transpentacins.
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A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate

15 April, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,2729-2736
DOI: 10.1039/C4OB00241E, PaperJanice M. H. Cheng, Emma M. Dangerfield, Mattie S. M. Timmer, Bridget L. Stocker
Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells.
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Copper-catalyzed highly efficient ester formation from carboxylic acids/esters and formates

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2637-2640
DOI: 10.1039/C4OB00193A, CommunicationJun Liu, Changdong Shao, Yanghui Zhang, Guangfa Shi, Shulei Pan
Copper-catalyzed ester formation from carboxylic acids/esters and formates has been developed with high efficiency and broad substrate scopes.
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Comparison of alternative nucleophiles for Sortase A-mediated bioconjugation and application in neuronal cell labelling

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2675-2685
DOI: 10.1039/C3OB42325E, PaperSamuel Baer, Julie Nigro, Mariusz P. Madej, Rebecca M. Nisbet, Randy Suryadinata, Gregory Coia, Lisa P. T. Hong, Timothy E. Adams, Charlotte C. Williams, Stewart D. Nuttall
Sortase A-mediated conjugation reactions were performed with a number of different nucleophiles. A peptide-Im7-labelled conjugate was used to image neuronal cells.
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Helical folding of [small alpha]/[small beta]-peptides containing [small beta]-amino acids with an eight-membered ring constraint

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2641-2644
DOI: 10.1039/C4OB00266K, CommunicationWoohyung Lee, Sunmi Kwon, Philjae Kang, Ilia A. Guzei, Soo Hyuk Choi
Cyclic [small beta]-amino acid that contains a cyclooctane or a cyclooctene ring promotes 11/9-helical folding of [small alpha]/[small beta]-peptides.
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An efficient ruthenium-catalyzed dehydrogenative synthesis of 2,4,6-triaryl-1,3,5-triazines from aryl methanols and amidines

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2761-2768
DOI: 10.1039/C3OB42589D, PaperFeng Xie, Mengmeng Chen, Xiaoting Wang, Huanfeng Jiang, Min Zhang
An efficient ruthenium-catalyzed dehydrogenative synthesis of 2,4,6-triaryl-1,3,5-triazines from aryl methanols and amidines has been demonstrated.
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An induced-fit process through mechanical pivoting of aromatic walls in host-guest chemistry of calix[6]arene aza-cryptands

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2754-2760
DOI: 10.1039/C4OB00304G, PaperAndrea Brugnara, Luca Fusaro, Michel Luhmer, Thierry Prange, Benoit Colasson, Olivia Reinaud
A rigid calix[6]arene-based receptor can be fully ipso-nitrated. The nitrated receptor exhibits a new adaptive behavior upon cation and/or guest encapsulation.
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Synthesis of [small alpha]-tribromomethylamines via Mg-mediated addition of bromoform to imines

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2769-2777
DOI: 10.1039/C4OB00259H, PaperElumalai Gopi, Irishi N. N. Namboothiri
N-Sulfonyl- and N-Boc-imines undergo facile addition of bromoform in the presence of Mg to afford [small alpha]-tribromomethyl N-sulfonyl- and N-Boc-amines.
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Synthesis of a multibranched porphyrin-oligonucleotide scaffold for the construction of DNA-based nano-architectures

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2778-2783
DOI: 10.1039/C4OB00202D, PaperGuillaume Clave, Gregory Chatelain, Arianna Filoramo, Didier Gasparutto, Christine Saint-Pierre, Eric Le Cam, Olivier Pietrement, Vincent Guerineau, Stephane Campidelli
A multiclick-based approach was used to build DNA-porphyrin hybrid platforms.
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Zwitterionic borane adducts of N-heterocyclic carbenes from mesomeric betaines of uracil

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2737-2744
DOI: 10.1039/C3OB42462F, PaperJiaxi Zhang, Nazar Pidlypnyi, Martin Nieger, Jan C. Namyslo, Andreas Schmidt
Imidazolium-substituted uracil-anions are in equilibrium with their N-heterocyclic carbenes which can be trapped as cyclic borane adducts.
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Rational design of catalysts for asymmetric diamination reaction using transition state modeling

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2745-2753
DOI: 10.1039/C3OB42520G, PaperGarima Jindal, Raghavan B. Sunoj
DFT calculations have been used to design chiral phosphoramidite ligands for the asymmetric diamination of vicinal diamines. The substituents at both the 3,3[prime or minute] positions of the binol framework and the amido nitrogen play a vital role in the stereochemical outcome.
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Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2686-2701
DOI: 10.1039/C3OB42521E, PaperCarmela Spatafora, Vincenza Barresi, Vedamurthy M. Bhusainahalli, Simone Di Micco, Nicolo Musso, Raffaele Riccio, Giuseppe Bifulco, Daniele Condorelli, Corrado Tringali
Twelve benzo[k,l]xanthene lignans were synthesized by biomimetic oxidative coupling of caffeic esters and amides. Their antiproliferative activity was evaluated on a panel of six tumor cell lines.
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Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2663-2674
DOI: 10.1039/C3OB42258E, PaperCatarina Carvalho, David Siegel, Martyn Inman, Rui Xiong, David Ross, Christopher J. Moody
Benzofuran- and benzimidazole-quinones are effective inhibitors of the tryptophan metabolizing enzyme indoleamine-2,3-dioxygenase (IDO).
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A computational and experimental study of O-glycosylation. Catalysis by human UDP-GalNAc polypeptide:GalNAc transferase-T2

13 April, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,2645-2655
DOI: 10.1039/C3OB42569J, PaperHansel Gomez, Raul Rojas, Divya Patel, Lawrence A. Tabak, Jose M. Lluch, Laura Masgrau
GalNAc-T2 catalyses GalNAc O-glycosylation via a front-side nucleophilic attack in which stabilization of the UDP leaving group is crucial.
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Synthesis of carbazole-based hetero-core-modified porphyrins

11 April, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,2656-2662
DOI: 10.1039/C3OB42564A, PaperChihiro Maeda, Motoki Masuda, Naoki Yoshioka
Annulation reaction of a 1,1[prime or minute]-(1,3-butadiyne)-8,8[prime or minute]-(2,5-thiophene)-bridged carbazole dimer 10 provided the carbazole-based isophlorines 11a-11c and 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13.
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