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Search for "nucleosides" in Full Text gives 123 result(s) in Beilstein Journal of Organic Chemistry.

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

  • Kazuhiro Okamoto,
  • Naoki Shida and
  • Mahito Atobe

Beilstein J. Org. Chem. 2024, 20, 264–271, doi:10.3762/bjoc.20.27

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  • avoided [9]. The initial aim of this study was the electrochemical generation of an amidyl radical as a HAT source for the synthesis of 1’-C functionalized nucleosides via the generation of an anomeric radical species from uridine derivative 1 (Figure 1, bottom) [10]. Although the HAT reaction failed
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Published 12 Feb 2024

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

  • Raphael Bereiter,
  • Marco Oberlechner and
  • Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

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  • nucleosides thereof [10][11][12], mostly associated with the inhibition of adenosine deaminase (ADA) [11] and as adenosine receptor antagonists [10]. Another important field of applications for deaza-modified nucleobases is their use in atom-specific mutagenesis experiments. For example, site specific 1-, 3
  • -, and 7-deazapurine mutations of RNA have been fundamental to shed light on their structure, catalysis, and function [13][14][15]. However, difficulties in these fields arise from the lack of efficient synthetic protocols for various deaza-nucleosides and nucleobases. This is particularly true for the
  • intermediates. Here, we present a new tactic for the syntheses of 1-deazaguanine and 1-deazahypoxanthine stimulated by a recently published route of our research group for the corresponding nucleosides [16][17], employing the same key reaction, namely the copper-catalyzed coupling of an aryl iodide with benzyl
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Published 29 Nov 2022

Ferrocenoyl-adenines: substituent effects on regioselective acylation

  • Mateja Toma,
  • Gabrijel Zubčić,
  • Jasmina Lapić,
  • Senka Djaković,
  • Davor Šakić and
  • Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

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  • the acylation of purines from a regioselective to a regiospecific mode. Keywords: DFT; ferrocene; nucleophilicity; purine; steric effect; Introduction Nucleosides in which the sugar part is replaced with an organometallic moiety have attracted remarkable interest [1][2][3]. One important class are
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Published 19 Sep 2022

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

  • Sandeep Kumar,
  • Jyotirmoy Maity,
  • Banty Kumar,
  • Sumit Kumar and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

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  • chemoenzymatic method was found to be superior over the chemical method in respect of the number of synthetic steps and overall yield of the final product. Keywords: bicyclic AZT analogues; bridged homoarabinofuranosylpyrimidine nucleosides; chemical pathway; Lipozyme® TL IM; regioselective enzymatic
  • chemotherapeutic agents used for the treatment of cancer were nucleoside analogues and nucleobases [10]. Azidothymidine (1, AZT) was the first approved drug for the treatment of human immunodeficiency virus (HIV) [11][12]. Subsequently, a large number of sugar modified nucleosides, such as ddC (zalcitabine) [13
  • azido-carbobicyclic nucleosides 2 and 3, where compound 2 showed activity similar to that of AZT while compound 3 was devoid of any type of activity (Figure 1). Nielsen et al. [22] synthesized the conformationally restricted nucleoside 4, which was devoid of any anti-HIV activity. Further, Zhang et al
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Published 11 Jan 2022

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

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  • Academy of Higher Education, Manipal-576104, Karnataka, India 10.3762/bjoc.17.182 Abstract Sugar-modified nucleosides have gained considerable attention in the scientific community, either for use as molecular probes or as therapeutic agents. When the methylene group of the ribose ring is replaced with a
  • accompanied by coupling nucleobases via N-glycosylation. However, over the last three decades, efforts were made for the synthesis of 1,3-oxathiolane nucleosides by selective N-glycosylation of carbohydrate precursors at C-1, and this approach has emerged as a strong alternative that allows simple
  • modification. This review aims to provide a comprehensive overview on the reported methods in the literature to access 1,3-oxathiolane nucleosides. The first focus of this review is the construction of the 1,3-oxathiolane ring from different starting materials. The second focus involves the coupling of the 1,3
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Published 04 Nov 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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Published 30 Jul 2021

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

  • Mathias B. Danielsen and
  • Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

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  • first reacted with either of the three diaminoalcohol groups, before subsequent phosphitylation with the DMT-protected nucleosides [115]. After incorporation into ONs, conversion to monomers 78–81 was accomplished as shown in Table 8. Although monomer 78 showed good yield in both phosphoramidite
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Published 29 Jul 2021

Development of N-F fluorinating agents and their fluorinations: Historical perspective

  • Teruo Umemoto,
  • Yuhao Yang and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

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  • ], electron-rich alkenes (entry 3) [65][66], alkyl sulfides (entry 4) [65][67], 1,3-dicarbonyl compounds [65][68], phosphonate esters (entry 5) [65], steroidal silyl enol ethers and enol acetates (entry 6) [65], pyrimidine bases and nucleosides (entry 7) [67][69], phenylalkynes (entry 8) [70], anthraquinones
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Published 27 Jul 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

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  • methodologies and the biological applications of double-headed nucleosides. Keywords: acyclic double-headed nucleosides; bicyclic double-headed nucleosides; furanosyl double-headed nucleosides; modified nucleosides; pyranosyl double-headed nucleosides; Introduction Nucleosides are the constructional subunits
  • of deoxyribonucleic acids (DNA) or ribonucleic acids (RNA), which contain either a purine or pyrimidine nucleobase and a furanosyl moiety of pentose sugars, 2′-deoxyribose or ribose [1][2]. Nucleotides are constituted by addition of a phosphate group at the 5′-position of the nucleosides and these
  • monomeric units polymerize to construct nucleic acids (DNA or RNA). These macromolecules preserve and express genetic information in all living cells and viruses. Modified nucleosides are a class of organic compounds which are unnatural and have an altered/substituted nucleobase and/or a modified pentose
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Published 08 Jun 2021

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

  • Christopher Liczner,
  • Kieran Duke,
  • Gabrielle Juneau,
  • Martin Egli and
  • Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

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  • diseases. Oligonucleotides with alterations to their scaffold, prepared with modified nucleosides and solid-phase synthesis, have yielded molecules with interesting biophysical properties that bind to their targets and are tolerated by the cellular machinery to elicit a therapeutic outcome. Structural
  • modifications reported by chemists along with the synthesis of 2'-deoxy-2'-fluoro-nucleosides (FRNA) [24]. The negatively charged phosphodiester linkages in the backbones of DNA and RNA are of fundamental importance for reactivity, stability, conformation and hydration [25][26]. The sugar moieties in DNA and
  • )-modified oligonucleotides was first described in 1991 by the Caruthers group [84]. Typically, each 2'-deoxynucleoside 3'-phosphorothioamidite is prepared by phosphitylating the protected nucleosides with tris(pyrrolidino)phosphine under tetrazole catalysis, followed by immediate treatment with
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Published 28 Apr 2021

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

  • Dace Cīrule,
  • Irina Novosjolova,
  • Ērika Bizdēna and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

Graphical Abstract
  • ring at the C6 position of purine to act as leaving group. Keywords: 2,6-bistriazolyl purines; nucleophilic aromatic substitution; purine nucleosides; triazoles; Introduction Modified purine derivatives are an important class of compounds which possess a wide spectrum of biological activities [1][2
  • compounds 5a–d. Synthetic pathways for the synthesis of 6-substituted 2-triazolylpurine derivatives IV. Synthesis of 2,6-bistriazolylpurine derivatives 2a–c. Synthesis of 6-alkyloxy-2-triazolylpurine derivatives 3a–f. Synthesis of 6-alkyloxy-2-triazolylpurine nucleosides 3g–j. 2,6-Bistriazolylpurine
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Published 11 Feb 2021

The preparation and properties of 1,1-difluorocyclopropane derivatives

  • Kymbat S. Adekenova,
  • Peter B. Wyatt and
  • Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

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  • targets of biological interest was provided by Csuk and Eversmann [32] who performed the synthesis of difluorinated nucleosides (Scheme 11). The difluorocyclopropane derivative 14 was prepared using sodium chlorodifluoroacetate (12) as a source of the carbene (Scheme 11). The subsequent deacetylation of
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Published 26 Jan 2021

1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

  • Kārlis-Ēriks Kriķis,
  • Irina Novosjolova,
  • Anatoly Mishnev and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

Graphical Abstract
  • activity against Mycobacterium tuberculosis and also as agonists and antagonists of adenosine receptors [18]. In 2013, we developed an efficient approach for the synthesis of ribo- and arabino-2,6-bistriazolylpurine nucleosides and showed that the triazolyl ring in the C6 position of purine acts as a good
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Published 20 Jan 2021

Incorporation of a metal-mediated base pair into an ATP aptamer – using silver(I) ions to modulate aptamer function

  • Marius H. Heddinga and
  • Jens Müller

Beilstein J. Org. Chem. 2020, 16, 2870–2879, doi:10.3762/bjoc.16.236

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  • for unnatural nucleosides). All natural nucleosides (A, T, G, and C), the fluorescein phosphoramidite as well as the DABCYL-CPGs were obtained from Glen Research. The oligonucleotides were deprotected and cleaved from the support by incubation in AMA solution (1:1, 40% methylamine and aqueous ammonia
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Published 25 Nov 2020

Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation

  • Jennifer Frommer and
  • Sabine Müller

Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234

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  • , functionalized phosphoramidite building blocks of all four nucleosides are highly desired. The number of commercially available RNA phosphoramidites that carry a suitable functionality for post-synthetic attachment of dyes, reporter groups or other conjugates is still rather limited. In particular, monomer
  • building blocks of the purine nucleosides with functionalities suitable for post-synthetic conjugation at the nucleobase are basically missing, and also in the pyrimidine series, the few existing derivatives of uridine do not offer much variety. Motivated by this lack of functional building blocks, we have
  • with the 3’-OH group, due its higher acidity [29]. For modified nucleosides, the preference of 2’-O-TBDMS formation in the presence of AgNO3 may not be given [29], and indeed, as already mentioned above, the C8-linker conjugated nucleoside derivative 7 (Scheme 1) shows the opposite behavior: the 3’-O
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Published 23 Nov 2020

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

  • Julia N. Artsemyeva,
  • Ekaterina A. Remeeva,
  • Tatiana N. Buravskaya,
  • Irina D. Konstantinova,
  • Roman S. Esipov,
  • Anatoly I. Miroshnikov,
  • Natalia M. Litvinko and
  • Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

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  • substrates of the phosphorolysis of uridine, thymidine, and 1-(β-ᴅ-arabinofuranosyl)uracil (Ara-U) catalyzed by recombinant E. coli uridine (UP) and thymidine (TP) phosphorylases. α-ᴅ-Pentofuranose-1-phosphates (PF-1Pis) obtained by phosphorolysis were used in the enzymatic synthesis of nucleosides. It was
  • PF-1Pis can be used in three routes: (1) preparation of barium salts of PF-1Pis, (2) synthesis of nucleosides by reacting the crude PF-1Pi with an heterocyclic base, and (3) synthesis of nucleosides by reacting the ionically bound PF-1Pi to the resin with an heterocyclic base. These three approaches
  • were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52–93%). Keywords: anion exchange resins; N6-benzyladenosine; cladribine; enzymatic glycosylation; kinetin riboside; nelarabine; α-ᴅ-pentofuranose-1-phosphates; phosphorolysis of nucleosides
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Published 22 Oct 2020

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

  • Patrizia Andreozzi,
  • Lorenza Tamberi,
  • Elisamaria Tasca,
  • Gina Elena Giacomazzo,
  • Marta Martinez,
  • Mirko Severi,
  • Marco Marradi,
  • Stefano Cicchi,
  • Sergio Moya,
  • Giacomo Biagiotti and
  • Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

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  • range of biomolecules: amino acids [8], peptides [9], glycosides [10], nucleosides/nucleotides [11], and lipids [12]. Also, protein-based nano-bio-conjugates [13] have been prepared by ball milling, retaining the native properties of the proteins after mechanochemical synthesis. Boronic acids and their
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Published 11 Sep 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

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  • N-heterocyclic compounds such as phenanthridine, carbazole, and dibenzo[b,d]azepine. Simultaneously, Guo’s group published the arylation of nucleosides bearing a purine moiety. The transformation was regioselective and tolerated various substituents at the N9 position of the purine, including sugar
  • features when working with biological systems. Thus, a variety of functionalized purines nucleosides that are potentially of great importance in medicinal chemistry were obtained in good yields. In contrast to C(sp2)–H bonds, C(sp3)–H bond activation is much more challenging. Inspired by the potential of
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Published 21 Jul 2020

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

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  • of anal gland secretions of the stoat [1] and the ferret [2]. Some pharmaceutical and biological thietane-containing compounds include thiaanalogue thietanose nucleosides 1 and 2 [3][4], and the spiroannulated glyco-thietane nucleoside 3 [5] of the antiviral (anti-HIV and HSV) drug oxetanocin A, the
  • 1966 [32]. They treated 3,5-dichloropentan-2-ol (9) with K2S to produce 1-(thietan-2-yl)ethan-1-ol (10) in 65% yield (Scheme 1). In 2007, Nishizono and co-workers used 2,2-bis(bromomethyl)propane-1,3-diol (11) as starting material to prepare thietanose nucleosides 2 and 14. They first carried out a
  • double displacement with sodium sulfide to obtain thietane-3,3-diyldimethanol (13), which was further converted into two different thietanose nucleosides 2 and 14 [33] (Scheme 2). In the synthesis of sesquiterpene thioalkaloids, the method also was utilized. A double-aldol condensation of methyl
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Published 22 Jun 2020

Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

  • Louise Ruyet and
  • Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

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  • ., glycals, nucleosides and nucleobases) [80]. In 2018, Hu and co-workers reported a complementary approach for the pentafluoroethylation of aryl iodides using TMSCF3 for the formation of CuCF2CF3 [81]. They suggested that in the presence of CuCl, KF and TMSCF3, the corresponding CuCF3 species will be formed
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Published 18 May 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

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  • previously reported methods required high temperatures [118][119][120]. A library of compounds was reported by that group using this approach, and a plausible mechanism is shown in Figure 13. Arylation of purines: Purine bases and purine nucleosides, which are common structural motifs in DNA and RNA, have an
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Published 26 Feb 2020

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

  • Renata Kaczmarek,
  • Dariusz Korczyński,
  • James R. Green and
  • Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

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  • confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series. Keywords: alkynes; 5-alkynyluridines; C–C-bond formation; dicobalt
  • hexacarbonyl complexes; Nicholas reaction; nucleosides; propargyl cation; Introduction Nucleoside analogs are molecules of high pharmacological interest for the treatment of various conditions, especially cancer and viral diseases [1][2][3][4][5]. The substitution at C-5 of the uracil nucleobase provides a
  • carbon monoxide-releasing properties [27][28] of dicobalt hexacarbonyl alkyne complexes have been noted, and their medicinal potential has been summarized [29][30][31]. Despite developments, the collection of metallo-nucleosides is limited. Hybridization of alkyl and aryl-substituted alkyne cobalt
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Published 02 Jan 2020

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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  • peptidyl nucleosides with primarily antifungal properties. The stereoselective synthesis of (+)-polyoxamic acid ((2S,3S,4S)-144) was successfully carried out starting with Horner–Wadsworth–Emmons olefination of the aziridine aldehyde (2R,1'R)-6 which provided a 98:2 mixture of trans- and cis-acrylates 69b
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Published 23 Jul 2019

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

  • Madhu Babu Tatina,
  • Xia Mengxin,
  • Rao Peilin and
  • Zaher M. A. Judeh

Beilstein J. Org. Chem. 2019, 15, 1275–1280, doi:10.3762/bjoc.15.125

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  • molecular recognition, cell–cell interaction, immunological recognition and transmission of biological information [4][5][6]. They are easily transformed into important bioactive compounds such as oligosaccharides, glycopeptides, nucleosides, antibiotics, uronic acids and other natural products [1][2][3
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Published 11 Jun 2019

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

  • Shahien Shahsavari,
  • Dhananjani N. A. M. Eriyagama,
  • Bhaskar Halami,
  • Vagarshak Begoyan,
  • Marina Tanasova,
  • Jinsen Chen and
  • Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

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  • removed with an acid in each synthetic cycle. The exo-amino groups of nucleosides dA, dC and dG are protected with acyl groups, the nascent ODN is anchored to a solid support via a base- or nucleophile-cleavable linker, and in the most widely used phosphoramidite technology the phosphate groups are
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Published 20 May 2019
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