Org. and Biomol. Chem.

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Synthesis and properties of oligonucleotides modified with 2[prime or minute]-O-(2-carboxyethyl)nucleotides and their carbamoyl derivatives

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01260G, PaperTakeshi Yamada, Yoshiaki Masaki, Natsuki Okaniwa, Takashi Kanamori, Akihiro Ohkubo, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
2[prime or minute]-O-Methyl oligoribonucleotides with four kinds of 2[prime or minute]-O-modified uridine derivatives were synthesised.
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Tautomerisation of thymine acts against the Huckel 4N + 2 rule. The effect of metal ions and H-bond complexations on the electronic structure of thymine

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00964A, PaperOlga A. Stasyuk, Halina Szatylowicz, Tadeusz M. Krygowski
Not necessarily the [small pi]-electron delocalization is responsible for the stability of thymine tautomers.
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Rational design of a new fluorescent 'ON/OFF' xanthene dye for phosphate detection in live cells

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00951G, PaperA. Martinez-Peragon, D. Miguel, A. Orte, A. J. Mota, M. J. Ruedas-Rama, J. Justicia, J. M. Alvarez-Pez, J. M. Cuerva, L. Crovetto
A new fluorescein derivative with ON/OFF features, 9-[1-(4-tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada Green, GG), was designed and synthesised.
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An efficient, Schiff-base derivative for selective fluorescence sensing of Zn2+ ions: quantum chemical calculation appended by real sample application and cell imaging study

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00732H, PaperSayantani Chall, Soumya Sundar Mati, Saugata Konar, Dipti Singharoy, Subhash Chandra Bhattacharya
Fluorescence based sensitive detection of the second most abundant metal ion (Zn2+) was established using a newly synthesized Schiff-base ligand, PyHP.
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Enantioselective synthesis of [small alpha],[small alpha]-difluoro-[small beta]-lactams using amino alcohol ligands

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01184H, PaperAtsushi Tarui, Takeshi Ikebata, Kazuyuki Sato, Masaaki Omote, Akira Ando
A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described.
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Enantioselective synthesis of [gamma]-tetrasubstituted nitrosulfonyl carboxylates and amides via L-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00344F, PaperKalisankar Bera, Irishi N. N. Namboothiri
A t-leucine-derived squaramide catalyzed reaction of [small alpha]-nitrosulfones with acrylates/acrylamides provides [gamma]-tetrasubstituted [gamma]-nitro-[gamma]-sulfonyl carboxylates/amides in excellent yield and enantioselectivity.
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Multicomponent reaction of chalcones, malononitrile and DMF leading to [gamma]-ketoamides

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00971A, PaperEnxiang Wei, Bing Liu, Shaoxia Lin, Fushun Liang
An efficient synthesis of [gamma]-ketoamides was developed by the one-pot multicomponent reaction of chalcones, malononitrile and DMF (as both the reactant and solvent) in the presence of NaOH (3.0 equiv.). The reaction features high atom economy, easily available starting materials, operational simplicity, and good tolerance with diverse functional groups.
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Electrochemical and theoretical analysis of the reactivity of shikonin derivatives: dissociative electron transfer in esterified compounds

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01207K, PaperGeorgina Armendariz-Vidales, Carlos Frontana
Electrochemical and theoretical analysis of Shikonin derivatives revealed that for esterified compounds, a dissociative electron transfer process occurs.
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An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00966E, PaperCarlos Areche, Beatriz Sepulveda, Aurelio San Martin, Olimpo Garcia-Beltran, Mario Simirgiotis, Alvaro Canete
An unusual mulinane diterpenoid named 7[small alpha]-acetoxy-9-epi-13[small beta]-hydroxymulinane was isolated from A. trifurcate. This compound possesses a new trans-syn-trans arrangement in a tricyclic ring system not previously encountered in nature.
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Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01132E, PaperYu-Chih Su, Yu-Lun Lo, Chi-Ching Hwang, Li-Fang Wang, Min Hui Wu, Eng-Chi Wang, Yun-Ming Wang, Tzu-Pin Wang
We have developed a universal approach for post-synthetic modifications of DNA/RNA by harnessing versatile phosphoramidation and powerful azide-alkyne cycloaddition reactions.
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00825A, PaperTakao Saito, Yoshihiko Sonoki, Takashi Otani, Noriki Kutsumura
A unique method for synthesis of structurally diverse types of indoles involving a triflic acid-promoted cycloisomerization and a Wagner-Meerwein-type rearrangement is described.
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Aliphatic amine responsive organogel system based on a simple naphthalimide derivative

21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00728J, PaperXinhua Cao, Tingting Zhang, Aiping Gao, Keli Li, Qiuli Cheng, Lijuan Song, Min Zhang
Aliphatic amines and aromatic amines were distinguished and detected by an organogel system containing naphthalimide.
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Azabicycles construction: the transannular ring contraction with N-protected nucleophiles

17 July, 2014 - 08:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01311E, Review ArticleAntonio Rizzo, Syuzanna R. Harutyunyan
Synthetic strategies are one of the most critical factors for the success of a synthetic campaign, but most importantly they are crucial for the economy and the efficiency of the sequence.
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Synthesis and immunological effects of heroin vaccines

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01053A, PaperFuying Li, Kejun Cheng, Joshua F. G. Antoline, Malliga R. Iyer, Gary R. Matyas, Oscar B. Torres, Rashmi Jalah, Zoltan Beck, Carl R. Alving, Damon A. Parrish, Jeffrey R. Deschamps, Arthur E. Jacobson, Kenner C. Rice
Multi-step syntheses provided three designed haptens for vaccines that were evaluated for their ability to block the effects of heroin and its metabolites.
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Mechanistic insight into benzenethiol catalyzed amide bond formations from thioesters and primary amines

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5745-5751
DOI: 10.1039/C4OB00073K, PaperNicolai Stuhr-Hansen, Nicolai Bork, Kristian Stromgaard
Thiophenol catalysed formations of amides from alkyl thioesters and primary amines in DMF were studied experimentally and theoretically.
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[Pd([small mu ]-Cl)Cl(IPr*)]2: a highly hindered pre-catalyst for the synthesis of tetra-ortho-substituted biaryls via Grignard reagent cross-coupling

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5586-5589
DOI: 10.1039/C4OB01269K, CommunicationMathieu Lesieur, Alexandra M. Z. Slawin, Catherine S. J. Cazin
The new well-defined catalyst [Pd([small mu ]-Cl)Cl(IPr*)]2 enables the efficient Grignard reagent cross-coupling for the synthesis of tetra-ortho-substituted biaryls.
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Diels-Alder reactions of 4-halo masked o-benzoquinones. Experimental and theoretical investigations

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5656-5668
DOI: 10.1039/C4OB00856A, PaperSeshi Reddy Surasani, Santosh Kumar Reddy Parumala, Rama Krishna Peddinti
The title reactions afforded densely substituted bicyclo-[2.2.2]octenones in high yields and high selectivities. The transition-state energies and global electronic indexes computed at the B3LYP/6-31G** theory level supported the observed selectivities of the reaction.
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A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01015A, PaperYang Wang, Donghui Wei, Wenjing Zhang, Yanyan Wang, Yanyan Zhu, Yu Jia, Mingsheng Tang
The reaction mechanisms between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles have been investigated using the DFT method.
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Exploring dual electrophiles in peptide-based proteasome inhibitors: carbonyls and epoxides

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5710-5718
DOI: 10.1039/C4OB00893F, PaperBo-Tao Xin, Gerjan de Bruin, Martijn Verdoes, Dmitri V. Filippov, Gijs A. van der Marel, Herman S. Overkleeft
Peptide epoxyketones are potent and selective proteasome inhibitors.
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Selective recognition of anionic cell membranes using targeted liposomes coated with zinc(II)-bis(dipicolylamine) affinity units

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5645-5655
DOI: 10.1039/C4OB00924J, PaperSerhan Turkyilmaz, Douglas R. Rice, Rachael Palumbo, Bradley D. Smith
Liposomes containing phospholipid-PEG conjugates with terminal zinc([i without dot][i without dot])-bis(dipicolylamine) affinity units selectively target anionic membrane surfaces including the exterior of bacterial and dead/dying mammalian cells.
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