Org. and Biomol. Chem.

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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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Development and application of serine/threonine ligation for synthetic protein chemistry

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3768-3773
DOI: 10.1039/C4OB00392F, PerspectiveHan Liu, Xuechen Li
The development and application of serine/threonine ligation (STL) in the synthesis of peptides/proteins and cyclic peptides have been reviewed.
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Improved selectivity of an engineered multi-product terpene synthase

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,4013-4020
DOI: 10.1039/C4OB00479E, PaperRyan Lauchli, Julia Pitzer, Rebekah Z. Kitto, Karolina Z. Kalbarczyk, Kersten S. Rabe
Random mutation of the multi-product sesquiterpene synthase Cop2 generated a mutant that converted the natural substrate farnesyl diphosphate (FPP) into germacrene D-4-ol with 77% selectivity without detrimental effects on wild-type kinetic properties.
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Chiral derivatives of 1,2-benzenedisulfonimide as efficient Bronsted acid catalysts in the Strecker reaction

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3902-3911
DOI: 10.1039/C4OB00552J, PaperMargherita Barbero, Silvano Cadamuro, Stefano Dughera, Roberta Torregrossa
Two chiral derivatives of 1,2-benzenedisulfonimide were synthesized. (-)Atropisomers have been demonstrated to be efficient chiral catalysts in the Strecker reaction.
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Palladium(II)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3866-3876
DOI: 10.1039/C4OB00367E, PaperRonny Hesse, Anne Jager, Arndt W. Schmidt, Hans-Joachim Knolker
Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A-E, O-methylmurrayamine A and O-methylmahanine) have been synthesised using a palladium(II)-catalysed cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.
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Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3774-3791
DOI: 10.1039/C3OB42554A, Review ArticleYong Ni, Jishan Wu
This review summarizes the general strategies to obtain far-red and NIR BODIPYs and their applications for pH probes and bio-imaging.
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Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of [small beta]-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3932-3943
DOI: 10.1039/C4OB00097H, PaperElizabeth V. Crabtree, R. Fernando Martinez, Shinpei Nakagawa, Isao Adachi, Terry D. Butters, Atsushi Kato, George W. J. Fleet, Andreas F. G. Glawar
A general structural trans-motif for the potent inhibition of [small beta]-N-acetylhexosaminidase by iminosugars emerges.
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A concise approach for the synthesis of bitungolides: total syntheses of (-)-bitungolide B & E

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,4002-4012
DOI: 10.1039/C4OB00250D, PaperK. Mahender Reddy, J. Shashidhar, Subhash Ghosh
The first total synthesis of (-)-bitungolide B and a second-generation total synthesis of (-)-bitungolide E are described through a common intermediate 13.
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Development of a new rhodamine-based FRET platform and its application as a Cu2+ probe

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3944-3949
DOI: 10.1039/C4OB00131A, PaperXiaoyu Guan, Weiying Lin, Weimin Huang
We have constructed a new rhodamine-based FRET platform, which was then used to develop a ratiometric fluorescent Cu2+ probe.
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Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3847-3865
DOI: 10.1039/C3OB42537A, PaperFaiz Ahmed Khan, Saeed Ahmad, Naveena Kodipelli, Gururaj Shivange, Roy Anindya
Analogues of marine natural products ianthelliformisamines were synthesized and evaluated for their biological activity, and two analogues showed promising bactericidal effects.
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[small beta]-Amyrin synthase from Euphorbia tirucalli. Steric bulk, not the [small pi]-electrons of Phe, at position 474 has a key role in affording the correct folding of the substrate to complete the normal polycyclization cascade

27 May, 2014 - 21:17

Org. Biomol. Chem., 2014, 12,3836-3846
DOI: 10.1039/C4OB00064A, PaperRyousuke Ito, Yukari Masukawa, Chika Nakada, Kanako Amari, Chiaki Nakano, Tsutomu Hoshino
The importance of the steric bulk at 474 residue is described for completion of the cyclization cascade, but not the [small pi]-electrons of the Phe residue.
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Continuous flow chemistry: a discovery tool for new chemical reactivity patterns

21 May, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,3611-3615
DOI: 10.1039/C4OB00662C, PaperJan Hartwig, Jan B. Metternich, Nikzad Nikbin, Andreas Kirschning, Steven V. Ley
A new reactivity pattern and extended reaction scope has been obtained by transferring a reaction from batch mode to flow.
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Peptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to [small alpha],[small beta],[gamma],[small delta]-unsaturated aldehydes

21 May, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,3581-3585
DOI: 10.1039/C4OB00565A, CommunicationKengo Akagawa, Nobuhiro Nishi, Jun Sen, Kazuaki Kudo
Addition of thiols to 2,4-dienals catalyzed by a resin-supported peptide gave thermodynamically favorable 1,6- and 1,4-diadducts in an enantioselective manner.
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Discrimination of adenine nucleotides and pyrophosphate in water by a zinc complex of an anthracene-based cyclophane

21 May, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,3701-3706
DOI: 10.1039/C4OB00184B, PaperPing Hu, Shengjun Yang, Guoqiang Feng
A zinc complex of an anthracene-based cyclophane was found to be a fluorescent sensor for ADP, ATP AMP and PPi in water at neutral pH.
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