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Search for "deazapurines" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of pyrrolo[3,2-d]pyrimidine-2,4(3H)-diones by domino C–N coupling/hydroamination reactions
- Ruben Manuel Figueira de Abreu,
- Robin Tiedemann,
- Peter Ehlers and
- Peter Langer
Beilstein J. Org. Chem. 2025, 21, 1010–1017, doi:10.3762/bjoc.21.82
- instance, deazapurines represent heterocyclic fused pyrimidine bases which have found special attention, due to their widespread occurrence in natural alkaloids exhibiting various biological properties. For example, cadeguomycin (A), tubercidin (B), and toyocamycin (C) show antibiotic properties, while
- leukaemia, and TAK-285 (H) is a promising HER2/EGFR inhibitor which has been tested in a phase 1 trial on humans as an anticancer agent (Figure 1) [16]. Given the significance of deazapurines as biologically active lead compounds [22], we developed a new methodology for the synthesis of uracil-based
Graphical Abstract
Figure 1: Development of drugs based on pyrrolopyrimidines: A: Cadeguomycin. B: Tubercidin. C: Toyocamycin. D...
Scheme 1: Synthesis of 3a–h. Conditions: i) Br2 (1.0 equiv), Ac2O (1.5 equiv), AcOH, 25 °C, 1 h [25]; ii) aryl ac...
Scheme 2: C–N cross-coupling/hydroamination reaction.
Scheme 3: Synthesis of 4a–m. Conditions: Pd(OAc)2 (5 mol %), DPEphos (5 mol %), K3PO4 (3 equiv), DMA, 100 °C,...
Figure 2: UV–vis absorption (left) and emission (right, λex = 300 nm) spectra of compounds 4a, 4j, 4k, 4l, an...
Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA
- Laurin Flemmich and
- Ronald Micura
Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35
- novel compound DPQ1. Keywords: deazapurines; heterocycles; pyrrolopyrimidines; queuosine; riboswitches; ribozymes; RNA alkylation; RNA labelling; Introduction Pre-queuosine 1 (preQ1) is a biosynthetic precursor of the hypermodified nucleoside queuosine (Q) that is found in the wobble position of
- aqueous hydrobromic acid provided 3c. Conclusion We have developed a divergent synthesis of 7-aminomethyl-7-deazapurines (preQ1 and DPQ1) with various electrophilic handles extending the aminomethyl moiety. These derivatives are capable of covalent tethering to the preQ1-I RNA aptamer. This aptamer occurs
Graphical Abstract
Scheme 1: A) Chemical structures of hypermodified nucleobase queuine and nucleoside queuosine (Q) occurring a...
Scheme 2: Three-step syntheses of preQ1 (1) and DPQ1 (2). For the synthesis of m6preQ1 (16) see Supporting Information File 1.
Scheme 3: Syntheses of haloalkyl- and mesyloxyalkyl-modified preQ1 as and DPQ1 ligands.
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
- nitration. A further strength of our route is divergency, additionally enabling the synthesis of 1-deazahypoxanthine (c1I base). Keywords: deazapurine; heterocycles; imidazopyridines; nucleoside; nucleotides; pyrrolopyrimidines; RNA atomic mutagenesis; Introduction Deazapurines (imidazopyridines and
Graphical Abstract
Scheme 1: Syntheses of C4-substituted diethyl 2,6-pyridinedicarbamates 4, passing hazardous and explosive dia...
Scheme 2: Synthesis of 1-deazaguanine (11) described by Markees and Kidder in 1956 [18].
Scheme 3: Synthesis of 1-deazaguanine (11) described by Gorton and Shive in 1957 [19].
Scheme 4: Six-step synthesis of 1-deazaguanine (11). Abbreviations: p-toluenesulfonic acid (TsOH), 4-(dimethy...
Scheme 5: 1-Deazahypoxanthine (30) synthesis described by Kubo and Hirao in 2019 [29]. For reason of simplicity o...
Scheme 6: Synthesis of 1-deazahypoxanthine (30).
Synthesis of O6-alkylated preQ1 derivatives
- Laurin Flemmich,
- Sarah Moreno and
- Ronald Micura
Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147
- scaffold. Keywords: deazapurines; heterocycles; pyrrolopyrimidines; queuosine; RNA cofactors; RNA methylation; Introduction Methylated preQ1 has attracted much attention recently because this compound has been found to function as cofactor for the conserved fold of a non-coding RNA, namely the preQ1
Graphical Abstract
Scheme 1: Chemical structures of queuine (Q base) and the hypermodified nucleoside queuosine (Q), the natural...
Scheme 2: Synthesis of compound 1 (m6preQ0) by cyclocondensation using a 4-methoxypyrimidine derivative resul...
Scheme 3: Synthesis of compound 3 following known procedures [31-33].
Scheme 4: The five-step synthesis of m6preQ1 2 from compound 3 required derivatization to make the intermedia...
Scheme 5: The synthesis of e6preQ1 (2a) and bn6preQ1 (2b) was performed in analogy to the route outlined in Scheme 4 ...
Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects
- Shivani Gulati,
- Stephy Elza John and
- Nagula Shankaraiah
Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71
Graphical Abstract
Figure 1: Marketed drugs with acridine moiety.
Scheme 1: Synthesis of 4-arylacridinediones.
Scheme 2: Proposed mechanism for acridinedione synthesis.
Scheme 3: Synthesis of tetrahydrodibenzoacridinones.
Scheme 4: Synthesis of naphthoacridines.
Scheme 5: Plausible mechanism for naphthoacridines.
Figure 2: Benzoazepines based potent molecules.
Scheme 6: Synthesis of azepinone.
Scheme 7: Proposed mechanism for azepinone formation.
Scheme 8: Synthesis of benzoazulenen-1-one derivatives.
Scheme 9: Proposed mechanism for benzoazulene-1-one synthesis.
Figure 3: Indole-containing pharmacologically active molecules.
Scheme 10: Synthesis of functionalized indoles.
Scheme 11: Plausible mechanism for the synthesis of functionalized indoles.
Scheme 12: Synthesis of spirooxindoles.
Scheme 13: Synthesis of substituted spirooxindoles.
Scheme 14: Plausible mechanism for the synthesis of substituted spirooxindoles.
Scheme 15: Synthesis of pyrrolidinyl spirooxindoles.
Scheme 16: Proposed mechanism for pyrrolidinyl spirooxindoles.
Figure 4: Pyran-containing biologically active molecules.
Scheme 17: Synthesis of functionalized benzopyrans.
Scheme 18: Plausible mechanism for synthesis of benzopyran.
Scheme 19: Synthesis of indoline-spiro-fused pyran derivatives.
Scheme 20: Proposed mechanism for indoline-spiro-fused pyran.
Scheme 21: Synthesis of substituted naphthopyrans.
Figure 5: Marketed drugs with pyrrole ring.
Scheme 22: Synthesis of tetra-substituted pyrroles.
Scheme 23: Mechanism for silica-supported PPA-SiO2-catalyzed pyrrole synthesis.
Scheme 24: Synthesis of pyrrolo[1,10]-phenanthrolines.
Scheme 25: Proposed mechanism for pyrrolo[1,10]-phenanthrolines.
Figure 6: Marketed drugs and molecules containing pyrimidine and pyrimidinones skeletons.
Scheme 26: MWA-MCR pyrimidinone synthesis.
Scheme 27: Two proposed mechanisms for pyrimidinone synthesis.
Scheme 28: MWA multicomponent synthesis of dihydropyrimidinones.
Scheme 29: Proposed mechanism for dihydropyrimidinones.
Figure 7: Biologically active fused pyrimidines.
Scheme 30: MWA- MCR for the synthesis of pyrrolo[2,3-d]pyrimidines.
Scheme 31: Proposed mechanism for pyrrolo[2,3-d]pyrimidines.
Scheme 32: Synthesis of substituted pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 33: Probable pathway for pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 34: Synthesis of pyridopyrimidines.
Scheme 35: Plausible mechanism for the synthesis of pyridopyrimidines.
Scheme 36: Synthesis of dihydropyridopyrimidine and dihydropyrazolopyridine.
Scheme 37: Proposed mechanism for the formation of dihydropyridopyrimidine.
Scheme 38: Synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 39: Plausible mechanism for the synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 40: Synthesis of decorated imidazopyrimidines.
Scheme 41: Proposed mechanism for imidazopyrimidine synthesis.
Figure 8: Pharmacologically active molecules containing purine bases.
Scheme 42: Synthesis of aza-adenines.
Scheme 43: Synthesis of 5-aza-7-deazapurines.
Scheme 44: Proposed mechanism for deazapurines synthesis.
Figure 9: Biologically active molecules containing pyridine moiety.
Scheme 45: Synthesis of steroidal pyridines.
Scheme 46: Proposed mechanism for steroidal pyridine.
Scheme 47: Synthesis of N-alkylated 2-pyridones.
Scheme 48: Two possible mechanisms for pyridone synthesis.
Scheme 49: Synthesis of pyridone derivatives.
Scheme 50: Postulated mechanism for synthesis of pyridone.
Figure 10: Biologically active fused pyridines.
Scheme 51: Benzimidazole-imidazo[1,2-a]pyridines synthesis.
Scheme 52: Mechanism for the synthesis of benzimidazole-imidazo[1,2-a]pyridines.
Scheme 53: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanedione derivatives.
Scheme 54: Proposed mechanism for spiro-pyridines.
Scheme 55: Functionalized macrocyclane-fused pyrazolo[3,4-b]pyridine derivatives.
Scheme 56: Mechanism postulated for macrocyclane-fused pyrazolo[3,4-b]pyridine.
Scheme 57: Generation of pyrazolo[3,4-b]pyridines.
Scheme 58: Proposed mechanism for the synthesis of pyrazolo[3,4-b]pyridines.
Scheme 59: Proposed mechanism for the synthesis of azepinoindole.
Figure 11: Pharmaceutically important molecules with quinoline moiety.
Scheme 60: Povarov-mediated quinoline synthesis.
Scheme 61: Proposed mechanism for Povarov reaction.
Scheme 62: Synthesis of pyrazoloquinoline.
Scheme 63: Plausible mechanism for pyrazoloquinoline synthesis.
Figure 12: Quinazolinones as pharmacologically significant scaffolds.
Scheme 64: Four-component reaction for dihydroquinazolinone.
Scheme 65: Proposed mechanism for dihydroquinazolinones.
Scheme 66: Synthesis purine quinazolinone and PI3K-δ inhibitor.
Scheme 67: Synthesis of fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 68: Proposed mechanism for fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 69: On-water reaction for synthesis of thiazoloquinazolinone.
Scheme 70: Proposed mechanism for the thiazoloquinazolinone synthesis.
Scheme 71: β-Cyclodextrin-mediated synthesis of indoloquinazolinediones.
Scheme 72: Proposed mechanism for synthesis of indoloquinazolinediones.
Figure 13: Triazoles-containing marketted drugs and pharmacologically active molecules.
Scheme 73: Cu(I) DAPTA-catalyzed 1,2,3-triazole formation.
Scheme 74: Mechanism for Cu(I) DAPTA-catalyzed triazole formation.
Scheme 75: Synthesis of β-hydroxy-1,2,3-triazole.
Scheme 76: Proposed mechanism for synthesis of β-hydroxy-1,2,3-triazoles.
Scheme 77: Synthesis of bis-1,2,4-triazoles.
Scheme 78: Proposed mechanism for bis-1,2,4-triazoles synthesis.
Figure 14: Thiazole containing drugs.
Scheme 79: Synthesis of a substituted thiazole ring.
Scheme 80: Synthesis of pyrazolothiazoles.
Figure 15: Chromene containing drugs.
Scheme 81: Magnetic nanocatalyst-mediated aminochromene synthesis.
Scheme 82: Proposed mechanism for the synthesis of chromenes.
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
- , the synthesis of C8-phosphonates of 7- and 9-deazapurines via C–H phosphonation has been reported [17]. On the other hand, azolylpurines are an important compound class that combines two recognized structural motifs of drug design – purines and azoles. Derivatives of this class are known for their
Graphical Abstract
Scheme 1: Structural diversity and synthetic methods of purinylphosphonates. MWI = microwave irradiation; LG ...
Scheme 2: Synthetic routes for the formation of purinylphosphonates 4.
Scheme 3: Synthesis of phosphonates 2, 7, and 8.
Scheme 4: Synthesis of phosphonic acid monoesters 3 and 7–9 as well as phosphonic acid 10.
Figure 1: Screenings of the rate for the ester group cleavage (conversion determined by NMR spectroscopy) in ...
Scheme 5: Synthesis of 2,6-bistriazolylpurine derivatives 6a–i.
Scheme 6: SNAr–Arbuzov reaction between the bistriazolylpurines 6a–i and P(OEt)3.
Figure 2: Single-crystal X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl...
Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines
- Andrejs Šišuļins,
- Jonas Bucevičius,
- Yu-Ting Tseng,
- Irina Novosjolova,
- Kaspars Traskovskis,
- Ērika Bizdēna,
- Huan-Tsung Chang,
- Sigitas Tumkevičius and
- Māris Turks
Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41
- -triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were
- to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future. Keywords: 7-deazapurines; fluorescence; nucleophilic aromatic substitution; purines; push–pull systems; pyrrolo[2,3-d]pyrimidines
- ] (Figure 1). 7-Deazapurines can be regarded as structurally close congeners to purines with an extra attachment point at their “artificially introduced” C(7). Therefore, it comes as no surprise that also 7-deazapurine derivatives containing heterocyclic substituents at various attachment points [26][27
Graphical Abstract
Figure 1: Examples of fluorescent purine/7-deazapurine derivatives.
Scheme 1: General synthetic routes for the compounds 5, 7–9, 10 and 11. Method A: alkyl halogenide, MeCN or D...
Figure 2: 1H NMR spectra of compound 6b in CD3CN at different temperatures (300 MHz, c = 12.5 mg/mL); a, b, c...
Figure 3: Comparison of 1H NMR spectra of compounds 8a and 5 (300 MHz, CDCl3).
Figure 4: a) Experimental UV–vis absorption spectra (lines) with computed theoretical absorption bands (colum...
Figure 5: Photos of compound 8c (A and B) and compound 11c (C and D) in THF, CHCl3, DMSO, MeCN and MeOH befor...
Figure 6: a) Fluorescence spectra of compounds 8c (λexc = 360 nm) and 11c (λexc = 370 nm) in solvents of diff...
Figure 7: Energy diagram for the frontier molecular orbitals of compounds 8a, 8c, 11a and 11c.
Figure 8: Labeled MCF-7 cells using compound 9 (C,D) and unlabeled MCF-7 cells (A,B) in microscope (2 h, c(9)...
Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
- Kartik Temburnikar and
- Katherine L. Seley-Radtke
Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65
- feature (hetero)aryl aromatic groups such as 9-deazapurines, pyrimidines, pyridines and phenyl groups connected by a C–C bond to a sugar (or sugar mimic) as shown in Figure 4 [30][45][46][47][50][54][55][56][57]. The change in the nature of the glycosidic bond is accompanied by i) increased hydrolytic
Graphical Abstract
Figure 1: Structural components of nucleic acids. Shown is the monomeric building block of nucleic acids. Cha...
Figure 2: Formation of oxocarbenium ion during glycosidic bond cleavage in nucleosides [31]. The extent of leavin...
Figure 3: Structural modifications to nucleobase-sugar connectivity. The O–C–N bond between nucleobase and su...
Figure 4: Examples of natural and synthetic C-nucleosides. Pseudouridine and formcycin are among several natu...
Figure 5: Synthetic approaches to C-nucleosides. A. Two common strategies for C-nucleoside synthesis involve ...
Figure 6: Steroselective C-nucleoside synthesis using D-ribonolactone. A. Nucleophilic substitution of D-ribo...
Figure 7: Synthesis of C1'-substituted 4-aza-7,9-dideazaadenine C-nucleosides [63-65,69,70]. A. Reaction of D-ribonolacton...
Figure 8: Pyrrolo- and imidazo[2,1-f][1,2,4]triazine C-nucleosides. A series of sugar- and nucleobase-substit...
Figure 9: Synthesis of 1',2'-cyclopentyl C-nucleoside [73]. Functional groups at C1' and C2' were installed and e...
Figure 10: Anti-influenza C-nucleosides mimicking favipiravir riboside [74]. A. Structure of favipiravir and its r...
Figure 11: Alternative method for synthesis of 2'-substituted C-nucleosides [75]. A. Synthesis of C2'-substituted ...
Figure 12: Synthesis of carbocyclic C-nucleosides using cyclopentanone [53]. A. Nucleophlic substitution on cyclop...
Figure 13: Synthesis of carbocyclic C-nucleosides via Suzuki coupling [53]. A. Synthesis of OTf-cyclopentene that ...
Strategies toward protecting group-free glycosylation through selective activation of the anomeric center
- A. Michael Downey and
- Michal Hocek
Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123
Graphical Abstract
Scheme 1: Solution-state conformations of D-glucose.
Scheme 2: Enzymatic synthesis of oligosaccharides.
Scheme 3: Enzymatic synthesis of a phosphorylated glycoprotein containing a mannose-6-phosphate (M6P)-termina...
Scheme 4: A) Selected GTs-mediated syntheses of oligosaccharides and other biologically active glycosides. B)...
Scheme 5: Enzymatic synthesis of nucleosides.
Scheme 6: Fischer glycosylation strategies.
Scheme 7: The basis of remote activation (adapted from [37]).
Scheme 8: Classic remote activation employing a MOP donor to access α-anomeric alcohols, carboxylates, and ph...
Figure 1: Synthesis of monoprotected glycosides from a (3-bromo-2-pyridyloxy) β-D-glycopyranosyl donor under ...
Scheme 9: Plausible mechanism for the synthesis of α-galactosides. TBDPS = tert-butyldiphenylsilyl.
Scheme 10: Synthesis of the 6-O-monoprotected galactopyranoside donor for remote activation.
Scheme 11: UDP-galactopyranose mutase-catalyzed isomerization of UDP-Galp to UDP-Galf.
Scheme 12: Synthesis of the 1-thioimidoyl galactofuranosyl donor.
Scheme 13: Glycosylation of MeOH using a self-activating donor in the absence of an external activator. a) Syn...
Scheme 14: The classical Lewis acid-catalyzed glycosylation.
Figure 2: Unprotected glycosyl donors used for the Lewis acid-catalyzed protecting group-free glycosylation r...
Scheme 15: Four-step synthesis of the phenyl β-galactothiopyranosyl donor.
Scheme 16: Protecting-group-free C3′-regioselective glycosylation of sucrose with α–F Glc.
Scheme 17: Synthesis of the α-fluoroglucosyl donor.
Figure 3: Protecting-group-free glycosyl donors and acceptors used in the Au(III)-catalyzed glycosylation.
Scheme 18: Synthesis of the mannosyl donor used in the study [62].
Scheme 19: The Pd-catalyzed stereoretentive glycosylation of arenes using anomeric stannane donors.
Scheme 20: Preparation of the protecting-group-free α and β-stannanes from advanced intermediates for stereoch...
Figure 4: Selective anomeric activating agents providing donors for direct activation of the anomeric carbon.
Scheme 21: One-step access to sugar oxazolines or 1,6-anhydrosugars.
Scheme 22: Enzymatic synthesis of a chitoheptaose using a mutant chitinase.
Scheme 23: One-pot access to glycosyl azides [73], dithiocarbamates [74], and aryl thiols using DMC activation and sub...
Scheme 24: Plausible reaction mechanism.
Scheme 25: Protecting-group-free synthesis of anomeric thiols from unprotected 2-deoxy-2-N-acetyl sugars.
Scheme 26: Protein conjugation of TTL221-PentK with a hyaluronan hexasaccharide thiol.
Scheme 27: Proposed mechanism.
Scheme 28: Direct two-step one-pot access to glycoconjugates through the in situ formation of the glycosyl azi...
Scheme 29: DMC as a phosphate-activating moiety for the synthesis of diphosphates. aβ-1,4-galactose transferas...
Figure 5: Triazinylmorpholinium salts as selective anomeric activating agents.
Scheme 30: One-step synthesis of DBT glycosides from unprotected sugars in aqueous medium.
Scheme 31: Postulated mechanism for the stereoselective formation of α-glycosides.
Scheme 32: DMT-donor synthesis used for metal-catalyzed glycosylation of simple alcohols.
Figure 6: Protecting group-free synthesis of glycosyl sulfonohydrazides (GSH).
Figure 7: The use of GSHs to access 1-O-phosphoryl and alkyl glycosides. A) Glycosylation of aliphatic alcoho...
Scheme 33: A) Proposed mechanism of glycosylation. B) Proposed mechanism for stereoselective azidation of the ...
Scheme 34: Mounting GlcNAc onto a sepharose solid support through a GSH donor.
Scheme 35: Lawesson’s reagent for the formation of 1,2-trans glycosides.
Scheme 36: Protecting-group-free protein conjugation via an in situ-formed thiol glycoside [98].
Scheme 37: pH-Specific glycosylation to functionalize SAMs on gold.
Figure 8: Protecting-group-free availability of phenolic glycosides under Mitsunobu conditions. DEAD = diethy...
Scheme 38: Accessing hydroxyazobenzenes under Mitsunobu conditions for the study of photoswitchable labels. DE...
Scheme 39: Stereoselective protecting-group-free glycosylation of D-glucose to provide the β-glucosyl benzoic ...
Figure 9: Direct synthesis of pyranosyl nucleosides from unactivated and unprotected ribose using optimized M...
Figure 10: Direct synthesis of furanosyl nucleosides from 5-O-monoprotected ribose in a one-pot glycosylation–...
Figure 11: Synthesis of ribofuranosides using a monoprotected ribosyl donor via an anhydrose intermediate.
Figure 12: C5′-modified nucleosides available under our conditions.
Scheme 40: Plausible reaction mechanism for the formation of the anhydrose.
Figure 13: Direct glycosylation of several aliphatic alcohols using catalytic Ti(Ot-Bu)4 in the presence of D-...
Figure 14: Access to glycosides using catalytic PPh3 and CBr4.
Figure 15: Access to ribofuranosyl glycosides as the major product under catalytic conditions. aLiOCl4 (2.0 eq...
A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA
- Heidi-Kristin Walter,
- Bettina Olshausen,
- Ute Schepers and
- Hans-Achim Wagenknecht
Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16
- phosphoramidite chemistry. The alkyne groups as reactive precursors are attached to the oligonucleotide [13], especially at the 5-position of pyrimidines [13], the 7-position of 7-deazapurines [14], and the 2’-position of ribofuranosides [11][15]. These positions were chosen since they are typically accepted by
Graphical Abstract
Scheme 1: 2’-Propargylated nucleosides as “clickable” DNA/RNA building blocks with ribo (1) and arabino (2) c...
Scheme 2: Synthesis of phosphoramidite 7 and modified DNA. a) TIPDSiCl2, pyridine, 2 h at 0 °C, 16 h at rt, 8...
Scheme 3: Structures of donor dyes D1–D4 as modifications of DNA2a and DNA2r and structures of acceptor dyes ...
Figure 1: Representative demonstration of the fluorescence readout differences between the four arabino/ribo ...
Figure 2: Confocal microscopy of HeLa cells after transfection with DNA2aD1–DNA3rD5 (row 1), DNA2rD1–DNA3aD8 ...
Multicomponent reactions in nucleoside chemistry
- Mariola Koszytkowska-Stawińska and
- Włodzimierz Buchowicz
Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179
- pyrrolidine hydrochlorides 16*HCl or 20a–c*HCl (Scheme 8), Evans et al. developed a concise synthesis of 1'-aza-analogs of immucilins, compounds 19 and 21 [67]. The amine hydrochlorides were treated in aq acetate buffer with aq formaldehyde and 9-deazaguanine 18a or a variety of deazapurines 18b–e. The
Graphical Abstract
Figure 1: Selected chemical modifications of natural ribose or 2'-deoxyribose nucleosides leading to the deve...
Scheme 1: (a) Classical Mannich reaction; (b) general structures of selected hydrogen active components and s...
Scheme 2: Reagents and reaction conditions: i. H2O or H2O/EtOH, 60–100 °C, 7 h–10 d; ii. H2, Pd/C or PtO2; ii...
Scheme 3: Reagents and reaction conditions: i. H2O, 90 °C, overnight.
Scheme 4: Reagents and reaction conditions: i. AcOH, H2O, 60 °C, 12 h-5 d; ii. AcOH, H2O, 60 °C, 8 h.
Scheme 5: Reagents and reaction conditions: i. CuBr, THF, reflux, 0.5 h; ii. n-Bu4NF·3H2O, THF, rt, 2 h.
Scheme 6: Reagents and reaction conditions: i. [bmim][PF6], 80 °C, 5–8 h.
Scheme 7: Reagents and reaction conditions: i. EtOH, reflux, 24 h.
Scheme 8: Reagents and reaction conditions: i. NaOAc, H2O, 95 °C, 1–16 h; ii. NaOAc, H2O, 95 °C, 1 h.
Scheme 9: Reagents and reaction conditions: i. a. 37% aq HCl, MeOH; b. NaOAc, 1,4-dioxane, H2O, 100 °C, overn...
Scheme 10: Reagents and reaction conditions: i. DMAP, DCC, MeOH, rt, 1 h.
Scheme 11: The Kabachnik–Fields reaction.
Scheme 12: Reagents and reaction conditions: i. 60 °C, 3 h; ii. 80 °C, 2 h.
Scheme 13: The four-component Ugi reaction.
Scheme 14: Reagents and reaction conditions: i. MeOH, rt, 2–3 d, yields not given.
Scheme 15: Reagents and reaction conditions: i. MeOH/CH2Cl2 (1:1), rt, 24 h, yield not given; ii. 6 N aq HCl, ...
Scheme 16: Reagents and reaction conditions: i. MeOH/H2O, rt, 26 h; ii. aq AcOH, reflux, 50%; iii. reversed ph...
Scheme 17: Reagents and reaction conditions: i. MeOH, rt, 24 h; ii. HCl, MeOH, 0 °C to rt, 6 h, then H2O, rt, ...
Scheme 18: Reagents and reaction conditions: i. DMF/Py/MeOH (1:1:1), rt, 48 h; ii. 10% HCl/MeOH, rt, 30 min.
Scheme 19: Reagents and reaction conditions (R = CH3 or H): i. CH2Cl2/MeOH (2:1), 35–40 °C, 2 d; ii. HF/pyridi...
Scheme 20: Reagents and reaction conditions: i. MeOH, 76%; ii. 80% aq TFA, 100%.
Scheme 21: Reagents and reaction conditions: i. EtOH, rt, 72 h; ii. Zn, aq NaH2PO4, THF, rt, 1 week; then 80% ...
Scheme 22: Reagents and reaction conditions: i. EtOH, rt, 48 h, then silica gel chromatography, 33% for 57 (30...
Scheme 23: Reagents and reaction conditions: i. [bmim]BF4, 80 °C, 4 h; ii. [bmim]BF4, 80 °C, 3 h; iii. [bmim]BF...
Scheme 24: Reagents and reaction conditions: i. [bmim]BF4, 80 °C.
Scheme 25: Reagents and reaction conditions: i. H3PW12O40 (2 mol %), EtOH, 50 °C, 2–15 h; ii. H3PW12O40 (2 mol...
Scheme 26: General scheme of the Biginelli reaction.
Scheme 27: Reagents and reaction conditions: i. EtOH, reflux.
Scheme 28: Reagents and reaction conditions: i. Bu4N+HSO4−, diethylene glycol, 120 °C, 1.5–3 h.
Scheme 29: Reagents and reaction conditions: i. BF3·Et2O, CuCl, AcOH, THF, 65 °C, 24 h; ii. Yb(OTf)3, THF, ref...
Scheme 30: Reagents and reaction conditions: TCT (10 mol %), rt: i. 100 min; ii. 150 min; iii. 140 min.
Scheme 31: Reagents and reaction conditions: i. EtOH, microwave irradiation (300 W), 10 min; ii. EtOH, 75 °C, ...
Scheme 32: The Hantzsch reaction.
Scheme 33: Reagents and reaction conditions: TCT (10 mol %), rt, 80–150 min.
Scheme 34: Reagents and reaction conditions: i. Yb(OTf)3, THF, 90 °C, 12 h; ii. 4 Å molecular sieves, EtOH, 90...
Scheme 35: Reagents and reaction conditions: i. MeOH, 50 °C, 48 h.
Scheme 36: Reagents and reaction conditions: i. MeOH, 25 °C, 5 d.
Scheme 37: Bu4N+HSO4−, diethylene glycol, 80 °C, 1–2 h.
Scheme 38: The three-component carbopalladation of dienes on the example of buta-1,3-diene.
Scheme 39: Reagents and reaction conditions: i. 5 mol % Pd(dba)2, Bu4NCl, ZnCl2, acetonitrile or DMSO, 80 °C o...
Scheme 40: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 41: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 42: The three-component Bucherer–Bergs reaction.
Scheme 43: Reagents and reaction conditions: i. MeOH, H2O, 70 °C, 4.5 h; ii. (1) H2, 5% Pd/C, MeOH, 55 °C, 5 h...
Scheme 44: Reagents and reaction conditions: i. pyridine, MgSO4, 100 °C, 28 h, N2; ii. DMF, 70–90 °C, 22–30 h,...
Scheme 45: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (600 W), 6–10...
Scheme 46: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (560 W), 6–10...
Scheme 47: Reagents and reaction conditions: i. CeCl3·7H2O (20 mol %), NaI (20 mol %), microwave irradiation (...
Scheme 48: Reagents and reaction conditions: i. PhI(OAc)2 (3 mol %), microwave irradiation (45 °C), 6–9 min.
Scheme 49: Reagents and reaction conditions: i. 117, ethyl pyruvate, TiCl4, dichloromethane, −78 °C, 1 h; then ...
