Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• previously used in the synthesis of PMO in the 2→4 direction [23]. This corresponds to the 5’→3’ direction of native oligonucleotides. In our case, the MorGly oligomers were synthesized in the opposite direction (4→2) [20] similar to the standard direction (3’→5’) of native ODN and peptide nucleic acid (PNA

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• switching of optical properties in DNA can be achieved selectively at 310 nm (forward) and 450 nm (backward); both wavelengths are outside the normal nucleic acid absorption range. Moreover, this nucleoside was proven to be photochemically stable and allows switching back and forth several times. These

• . Hence, the absorption side band at 310 nm should allow, at least in principal, the selective excitation of the switch, outside the nucleic acid absorption range. Accordingly, the photoswitching of 4 was probed at 242 and 310 nm. In fact, by irradiation at either wavelength the closed form of nucleoside

• properties of the nucleosides were evaluated and revealed that only nucleoside 4 allows selective excitation at 310 nm, outside the nucleic acid absorption window, to close the diarylethene chromophore. Switching back of the colored form of all three nucleosides 4–6 to the corresponding opened forms can be

Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size

• Patrick Claude,
• Christian Lehmann and
• Thomas Ziegler

Beilstein J. Org. Chem. 2011, 7, 1609–1619, doi:10.3762/bjoc.7.189

• glycosidic oxygen in the equatorial orientation. Similar, possibly less-spectacular cases of product-controlling ASI effects have notably been found in peptide cyclization reactions [48][49] and very generally for the case of the induction of handedness in nucleic acid constructs ([50] and references cited

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• , cytotoxic and antibacterial, is also reported. Keywords: 5-alkoxymethyluracil; biological activity; nucleosides; Review Introduction Modifications of nucleic acid components play a significant role in the field of nucleic acids research. In particular, nucleoside analogues find broad therapeutic

• and finally treated with methanolic ammonia to afford nucleosides 126 and 127. Synthesis of oligonucleotide intermediates Modified oligonucleotides are powerful tools in nucleic acid research and their synthesis has become an important aspect of bioorganic and medicinal chemistry. One part of

Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid

• Yanmei Zhang,
• Greg Elliot,
• Adrian Saldanha,
• Igor Tsigelny,
• Dennis Carson and
• Wolf Wrasidlo

Beilstein J. Org. Chem. 2010, 6, 742–747, doi:10.3762/bjoc.6.93

• thiolated nucleoside to obtain the hybrid model compound. Keywords: adenylosuccinate synthetase (AdSS); thiolated nucleoside; Introduction During cell proliferation, adenine nucleotides for nucleic acid synthesis are generated through a de novo biosynthetic route, which requires the key enzyme

Anthracene coupled adenine for the selective sensing of copper ions

• Kumaresh Ghosh and
• Tanushree Sen

Beilstein J. Org. Chem. 2010, 6, No. 44, doi:10.3762/bjoc.6.44

• ]. Although there are various reports in this regard, synthetic receptors with improved binding efficiency are still in demand. In addition, the coordination of the metal ion with nucleobases plays an important role in the stability of the nucleic acid structure [25]. Among the nucleobases adenine provides

Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• the 2′-deoxyriboside between the phosphodiester bridges. Similar propanediol derivatives have been used extensively as alternative and simplified phosphodiester linkers in the 1990s [19][20][21][22][23], and have been further explored for glycol nucleic acid (GNA) [24][25][26] twisted intercalating

Synthesis of 2-substituted 9-oxa-guanines {5-aminooxazolo[5,4-d]pyrimidin- 7(6H)-ones} and 9-oxa-2-thio- xanthines {5-mercaptooxazolo[5,4-d]pyrimidin- 7(6H)-ones}

• Subrata Mandal,
• Wen Tai Li,
• Yan Bai,
• Jon D. Robertus and
• Sean M. Kerwin

Beilstein J. Org. Chem. 2008, 4, No. 26, doi:10.3762/bjoc.4.26

• can be considered as 9-oxa-purine analogs of naturally occurring nucleic acid bases. Interest in this ring system has increased due to recent reports of biologically active derivatives. In particular, 5-aminooxazolo[5,4-d]pyrimidine-7(6H)-ones (9-oxa-guanines) have been shown to inhibit ricin. The

• to naturally occurring nucleic acid bases, this heterocyclic ring system continues to generate interest. Approaches to the oxazolo[5,4-d]pyrimidine ring system generally involve either cyclodehydration of an 5-(acylamino)-4-hydroxypyrimidine [6][7][8][9][10] or elaboration of a 4-cyano- or 4

N-1 regioselective Michael- type addition of 5-substituted uracils to (2-hydroxyethyl) acrylate

• Sławomir Boncel,
• Dominika Osyda and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2007, 3, No. 40, doi:10.1186/1860-5397-3-40

• literature for acyclic nucleosides.[1] Acyclic units containing hydroxyl groups are capable of phosphorylation and building into a growing nucleic acid, thus perturbing its replication. Several acyclic nucleosides, like HEPT (1-[2-hydroxyethoxymethyl]-6-(phenylthio)thymine),[2] or MKC-442 (1-ethoxymethyl-5

Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• different approaches for modification of nucleic acid components and DNA biosensor construction have been developed, many questions remain to be answered with respect to the complete understanding of optical and electrical properties of modified nucleic acids used in bioanalytical systems. Universal