Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• peptidyl carrier protein (PCP) of the downstream NRPS module is loaded with an L-cysteine, which serves as a sulphur donor. From 177, sulphur is transferred by the NifS-like cysteine desulphurase TlmS to the tRNA-specific and adenosine triphosphate (ATP)-dependent 2-thiouridylase TlmJ, which is thereby

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• -catalysed displacement of the uracil with a phosphate moiety to afford 5-amino-5-deoxyribose-1-phosphate (116). The LipM-mediated reaction of ribosyl phosphate 116 with a nucleoside triphosphate (NTP) then yields nucleoside diphosphate (NDP)-aminoribose 117. Finally, aminoribosylation of 101 with glycosyl

Two strategies for the synthesis of the biologically important ATP analogue ApppI, at a multi-milligram scale

• Janne Weisell,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2015, 11, 2189–2193, doi:10.3762/bjoc.11.237

• Janne Weisell Jouko Vepsalainen Petri A. Turhanen University of Eastern Finland, School of Pharmacy, Biocenter Kuopio, P.O. Box 1627, FIN-70211, Kuopio, Finland 10.3762/bjoc.11.237 Abstract Two strategies for the synthesis of the ATP (adenosine triphosphate) analogue ApppI [1-adenosin-5’-yl 3-(3

DNA display of glycoconjugates to emulate oligomeric interactions of glycans

• Alexandre Novoa and
• Nicolas Winssinger

Beilstein J. Org. Chem. 2015, 11, 707–719, doi:10.3762/bjoc.11.81

• enzymatically using glycan-functionalized desoxyuridine triphosphate as substrate with KOD Dash DNA polymerase [23]. The applicability of the method was illustrated with the incorporation of multiple units of lactose or maltose in different DNA sequences. The same group used this technology to prepare

•  6). At first, a library of single strand DNA with a hairpin is extended with a polymerase replacing dTTP by an alkyne-modified desoxyuridine triphosphate to give a full hairpin with randomized alkyne groups on one strand. Then, CuAAC is performed with a glycosyl azide and the hairpin is released by

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• antimicrobial activity by inhibition of the lipid synthesis and some enzymes whereas butylparaben is assumed to influence the mitochondrial depolarization depletion of cellular adenosine triphosphate. However, the biocidal activity of the CP-β-CD alone is clearly different from the other cationic biocides or

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

• Vicky Gheerardijn,
• Jos Van den Begin and
• Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

• no need for protection of the functional groups. For example, many imidazole and amine functionalities were incorporated to increase the structural diversity and catalytic potential of nucleic acids [34][35][36][37]. Most of these functionalities are introduced into the triphosphate building blocks

Autonomous assembly of synthetic oligonucleotides built from an expanded DNA alphabet. Total synthesis of a gene encoding kanamycin resistance

• Kristen K. Merritt,
• Kevin M. Bradley,
• Daniel Hutter,
• Mariko F. Matsuura,
• Diane J. Rowold and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 2348–2360, doi:10.3762/bjoc.10.245

• nucleotide opposite an AEGIS nucleotide by (a) not being provided the complementary AEGIS triphosphate and (b) exploiting a chemical feature of the AEGIS nucleotide that directs a specific mismatch. For example, when the AEGIS nucleotide 2’-deoxy-5-methylisocytidine (trivially designated S) and its AEGIS

OligArch: A software tool to allow artificially expanded genetic information systems (AEGIS) to guide the autonomous self-assembly of long DNA constructs from multiple DNA single strands

• Kevin M. Bradley and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 1826–1833, doi:10.3762/bjoc.10.192

• nucleotides with standard nucleotides by depriving the polymerase of the complementary AEGIS triphosphate. The specificity of mismatching is driven by intrinsic features of the AEGIS nucleobase. Thus, the B:T mismatch is enabled by a minor tautomeric form of B. The Z:G mismatch is enabled by the deprotonation

Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs

• Fabrizio Chiodo,
• Marco Marradi,
• Javier Calvo,
• Eloisa Yuste and
• Soledad Penadés

Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136

• activity or acid conditions in the cellular medium (or vaginal acidic pH). The primary hydroxy group of these NRTIs is fundamental for their antiviral activity: its intracellular enzymatic phosphorylation will form triphosphate derivatives that are the real chain terminators of HIV reverse transcriptase [3

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ₀)

• Sabin Llona-Minguez and
• Simon P. Mackay

Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135

• , respectively [5][6]. In turn, the biosynthesis of PreQ0 originates from guanosine 5’-triphosphate (GTP, 4) [7] (Figure 1) and involves four steps via a tetrahydropterine intermediate. The pyrrolo[2,3-d]pyrimidine core is a privileged scaffold for the development of kinase inhibitors; an inspection of the

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

• , after purification, the triphosphate in 68% yield. Generally, the first protocol is preferred to avoid any hydrolysis of chlorophosphate, which could be explained by the presence of trace amounts of water. As indicated above, a tertiary amine is the preferred base for the AT reaction. However, primary

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• kinase; ATP: adenosine triphosphate; PEP: phosphoenolpyruvate; CTP: cytidine triphosphate; PPi: pyrophosphate; DNA: deoxyribonucleic acid; mRNA: messenger ribonucleic acid. Proposed metabolic pathway of Neu5Hex 3 based on known mechanisms of Neu5Gc 2 uptake [5]. TGN: trans-Golgi network, CMP: cytidine

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

• ]. Inhibition by these mechanisms results in adenosine triphosphate (ATP) deprivation, which leads to apoptosis of the highly energy demanding tumor cells [11]. The acetogenins are now considered as the most potent (effective in nanomolar concentrations) known inhibitors of the mitochondrial complex I [9][12