Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Aziridine electrophiles in the functionalisation of peptide chains with amine nucleophiles

11 August, 2015 - 08:54

Org. Biomol. Chem., 2015, 13,8545-8549
DOI: 10.1039/C5OB00856E, PaperAnatol P. Spork, Timothy J. Donohoe
We describe herein the synthesis of aziridine-containing amino acids embedded within tripeptide structures.
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A facile approach to [small beta]-amino acid derivatives via palladium-catalyzed hydrocarboxylation of enimides with formic acid

11 August, 2015 - 08:54

Org. Biomol. Chem., 2015, 13,8429-8432
DOI: 10.1039/C5OB01304F, CommunicationJie Dai, Wenlong Ren, Haining Wang, Yian Shi
An effective Pd(0)-catalyzed hydrocarboxylation of enimides with formic acid in the presence of a catalytic amount of HCOOPh is described.
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Synthesis and biological evaluation of hybrid acridine-HSP90 ligand conjugates as telomerase inhibitors

11 August, 2015 - 08:54

Org. Biomol. Chem., 2015, 13,8500-8504
DOI: 10.1039/C5OB01177A, PaperS. Roe, M. Gunaratnam, C. Spiteri, P. Sharma, R. D. Alharthy, S. Neidle, J. E. Moses
The synthesis and biological evaluation of a series of bifunctional acridine-HSP90 inhibitor ligands as telomerase inhibitors is herein described.
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Optimized quinoline amino alcohols as disruptors and dispersal agents of Vibrio cholerae biofilms

9 August, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,8495-8499
DOI: 10.1039/C5OB01134E, PaperBrian Leon, F. P. Jake Haeckl, Roger G. Linington
The biofilm state is an integral part of the lifecycle of many bacterial pathogens, but no treatments currently exist that directly impact biofilm formation or persistence. Here we report the development of a quinoline amino alcohol scaffold with both biofilm inhibitory and biofilm dispersal activities against the human pathogen Vibrio cholerae.
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Iridium/copper-cocatalyzed asymmetric ring opening reaction of azabenzonorbornadienes with amines

9 August, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,8425-8428
DOI: 10.1039/C5OB01243K, CommunicationChaoyuan Zeng, Fan Yang, Jingchao Chen, Jun Wang, Baomin Fan
Chiral trans-vicinal diamines were synthesized via an asymmetric ring opening reaction of azabenzonorbornadienes with amines.
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Synthesis and evaluation of 2-ethynyl-adenosine-5[prime or minute]-triphosphate as a chemical reporter for protein AMPylation

9 August, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,8550-8555
DOI: 10.1039/C5OB01081K, PaperChrista Creech, Mukul Kanaujia, Corey P. Causey
2-Ethynyl-adenosine-5[prime or minute]-triphosphate is a chemical reporter for AMPylation that enables visualization of modified protein substrates.
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Smaller, faster, better: modular synthesis of unsymmetrical ammonium salt-tagged NHC-gold(I) complexes and their application as recyclable catalysts in water

9 August, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,8556-8560
DOI: 10.1039/C5OB01286D, PaperKatrin Belger, Norbert Krause
Facile access towards unsymmetrical ammonium salt-tagged NHC-gold(I) complexes is described, and their application as recyclable catalysts in cyclization reactions of acetylenic carboxylic acids and amides in aqueous media is demonstrated.
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Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives

9 August, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,8465-8469
DOI: 10.1039/C5OB00944H, PaperGesine K. Veits, Donald R. Wenz, Leoni I. Palmer, Andre H. St. Amant, Jason E. Hein, Javier Read de Alaniz
The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.
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Acid-promoted cycloisomerizations of phenylallenes bearing acetalic functions at the ortho position: a stereocontrolled entry to indeno-fused dioxepanes, dioxocanes and thioanalogues

7 August, 2015 - 07:54

Org. Biomol. Chem., 2015, 13,8420-8424
DOI: 10.1039/C5OB00897B, CommunicationMarta Marin-Luna, Angel Vidal, Delia Bautista, Raul-Angel Orenes, Mateo Alajarin
Two different approaches convert ortho acetal-substituted phenylallenes into several classes of indeno-fused heterocycles.
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An atom-economic approach to carboxylic acids via Pd-catalyzed direct addition of formic acid to olefins with acetic anhydride as a co-catalyst

7 August, 2015 - 07:54

Org. Biomol. Chem., 2015, 13,8416-8419
DOI: 10.1039/C5OB01180A, CommunicationYang Wang, Wenlong Ren, Yian Shi
An effective Pd-catalyzed hydrocarboxylation of olefins using formic acid with acetic anhydride as a co-catalyst is described.
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Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines

7 August, 2015 - 07:54

Org. Biomol. Chem., 2015, 13,8411-8415
DOI: 10.1039/C5OB01196E, CommunicationSadhan Jana, Athira Ashokan, Shailesh Kumar, Ajay Verma, Sangit Kumar
A ligand and base free copper catalyzed method has been developed for the construction of trifluoromethylated benzoxazines by using Umemoto's reagent.
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A theoretical investigation of substituent effects on the stability and reactivity of N-heterocyclic olefin carboxylates

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8533-8544
DOI: 10.1039/C5OB01021G, PaperLiang Dong, Jun Wen, Weiyi Li
Introduction of four phenyl groups at C-position and N-position not only favors decarboxylation but also ensures NHO as a strong nucleophile.
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Formation and aromatization of strained bicyclic pyrazolidines via tandem reaction of alkyl 2-aroyl-1-chlorocyclopropanecarboxylates with acylhydrazones

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8561-8566
DOI: 10.1039/C5OB01199J, PaperZhimei Huang, Junhao Hu, Yuefa Gong
The formation and aromatization of strained bicyclic pyrazolidines.
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Efficient routes towards a series of 5,5[prime or minute]-bithiazolidinylidenes as [small pi]-electron acceptors

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8479-8486
DOI: 10.1039/C5OB01169H, PaperY. Le Gal, D. Ameline, N. Bellec, A. Vacher, T. Roisnel, V. Dorcet, O. Jeannin, D. Lorcy
Among different approaches, the thermal treatment of the fused bicycle involving a dithiole-2-one ring is the most efficient one and opens access to a variety of [small pi]-conjugated electron acceptors.
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Cu(OAc)2-promoted reaction of [60]fullerene with primary amines or diamines

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8405-8410
DOI: 10.1039/C5OB01048A, CommunicationXin-Wei Lu, Meng-Lei Xing, Chun-Bao Miao, Jia-Xing Li, Xiao-Qiang Sun, Hai-Tao Yang
The Cu(OAc)2-mediated oxidative dehydrogenative addition of easily available primary amines to C60 allows the concise preparation of aziridinofullerenes. Moreover, the Cu(OAc)2-promoted reaction of C60 with diamines affords C60-fused cyclic 1,2-diaminated fullerenes.
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The first proton sponge-based amino acids: synthesis, acid-base properties and some reactivity

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8524-8532
DOI: 10.1039/C5OB01065A, PaperValery A. Ozeryanskii, Anastasia Yu. Gorbacheva, Alexander F. Pozharskii, Marina P. Vlasenko, Alexander Yu. Tereznikov, Margarita S. Chernov'yants
The first hybrid bases constructed from 1,8-bis(dimethylamino)naphthalene and glycine or alanine residues were synthesised and structurally characterised and unusual channels of their reactivity revealed.
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Leishmania cell wall as a potent target for antiparasitic drugs. A focus on the glycoconjugates

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8393-8404
DOI: 10.1039/C5OB00563A, Review ArticleYari Cabezas, Laurent Legentil, Florence Robert-Gangneux, Franck Daligault, Sorya Belaz, Caroline Nugier-Chauvin, Sylvain Tranchimand, Charles Tellier, Jean-Pierre Gangneux, Vincent Ferrieres
The basic structure of membrane glycoconjugates in Leishmania still inspires therapeutic drugs fighting against this parasite.
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Cyclic acetals as cleavable linkers for affinity capture

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8445-8452
DOI: 10.1039/C5OB01056J, PaperSiyeon Lee, Wei Wang, Younjoo Lee, Nicole S. Sampson
A cyclic acetal moiety is an acid-sensitive linker for affinity capture and which provides an aldehyde for further elaboration.
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Divergent synthesis of various iminocyclitols from D-ribose

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8512-8523
DOI: 10.1039/C5OB01042J, PaperRamu Petakamsetty, Vipin Kumar Jain, Pankaj Kumar Majhi, Ramesh Ramapanicker
A very efficient route to the diastereoselective synthesis of polyhydroxy pyrrolidines, piperidines and azepanes from an aldehyde derivative of ribose is reported.
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A quantum chemical study of the [small omega]-transaminase reaction mechanism

5 August, 2015 - 07:18

Org. Biomol. Chem., 2015, 13,8453-8464
DOI: 10.1039/C5OB00690B, PaperKarim Engelmark Cassimjee, Bianca Manta, Fahmi Himo
The detailed half-transamination mechanism of Chromobacterium violaceum [small omega]-transaminase is investigated by means of density functional theory calculations.
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