Click Reaction on Solid Phase Enables High Fidelity Synthesis of Nucleobase-Modified DNA

2016 ◽  
Vol 27 (3) ◽  
pp. 500-503 ◽  
Author(s):  
Fabian Tolle ◽  
Malte Rosenthal ◽  
Franziska Pfeiffer ◽  
Günter Mayer
Keyword(s):  
Solid Phase ◽  
Click Reaction ◽  
High Fidelity ◽  
Modified Dna

Synthetic Routes for 1,4-disubstituted 1,2,3-triazoles: A Review

2019 ◽  
Vol 23 (8) ◽  
pp. 860-900 ◽  
Author(s):  
Chander P. Kaushik ◽  
Jyoti Sangwan ◽  
Raj Luxmi ◽  
Krishan Kumar ◽  
Ashima Pahwa
Keyword(s):  
Solid Phase ◽  
Click Reaction ◽  
Biological Activities ◽  
Triazole Ring ◽  
Copper Catalysts ◽  
Biologically Active ◽  
Pharmaceutical Chemistry ◽  
Biological Targets ◽  
Synthetic Routes ◽  
High Yields

N-Heterocyclic compounds like 1,2,3-triazoles serve as a key scaffolds among organic compounds having diverse applications in the field of drug discovery, bioconjugation, material science, liquid crystals, pharmaceutical chemistry and solid phase organic synthesis. Various drugs containing 1,2,3-triazole ring which are commonly available in market includes Rufinamide, Cefatrizine, Tazobactam etc., Stability to acidic/basic hydrolysis along with significant dipole moment support triazole moiety for appreciable participation in hydrogen bonding and dipole-dipole interactions with biological targets. Huisgen 1,3-dipolar azide-alkyne cycloaddition culminate into a mixture of 1,4 and 1,5- disubstituted 1,2,3-triazoles. In 2001, Sharpless and Meldal came across with a copper(I) catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles by cycloaddition between azides and terminal alkynes. This azide-alkyne cycloaddition has been labelled as a one of the important key click reaction. Click synthesis describes chemical reactions that are simple to perform, gives high selectivity, wide in scope, fast reaction rate and high yields. Click reactions are not single specific reaction, but serve as a pathway for construction of simple to complex molecules from a variety of starting materials. In the last few decades, 1,2,3-triazoles attracted attention of researchers all over the world because of their broad spectrum of biological activities. Keeping in view the biological importance of 1,2,3-triazole, in this review we focus on the various synthetic routes for the syntheisis of 1,4-disubstituted 1,2,3-triazoles. This review involves various synthetic protocols which involves copper and non-copper catalysts, different solvents as well as substrates. It will boost synthetic chemists to explore new pathway for the development of newer biologically active 1,2,3-triazoles.

scholarly journals Magnetic γFe2O3@Sh@Cu2O: an efficient solid-phase catalyst for reducing agent and base-free click synthesis of 1,4-disubstituted-1,2,3-triazoles

BMC Chemistry ◽  
2020 ◽  
Vol 14 (1) ◽  
Author(s):  
Fereshteh Norouzi ◽  
Shahrzad Javanshir
Keyword(s):  
Photoelectron Spectroscopy ◽  
Inductively Coupled Plasma ◽  
Solid Phase ◽  
Click Reaction ◽  
Copper Acetate ◽  
Reducing Agent ◽  
Gravimetric Analysis ◽  
High Turnover ◽  
One Pot ◽  
X Ray

AbstractA hybrid magnetic material γFe2O3@Sh@cu2O was easily prepared from Shilajit (Sh) decorated Fe3O4 and copper acetate. The prepared magnetic hybrid material was fully characterized using different analysis, including Fourier transform infrared (FT-IR), X-ray diffraction (XRD), inductively coupled plasma (ICP), scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectroscopy (XPS), vibrating sample magnetometer (VSM) thermal gravimetric analysis (TGA) and Brunauer–Emmett–Teller (BET). All these analysis revealed that during coating of Fe3O4@Sh using copper salt (II), synchronized redox sorption of CuII to CuI occurs at the same time as the oxidation of Fe3O4 to γFe2O3. This magnetic catalyst exhibited excellent catalytic activity for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles via one pot three-component click reaction of sodium azide, terminal alkynes and benzyl halides in the absence of any reducing agent. High yields, short reaction time, high turnover number and frequency (TON = 3.5 * 105 and TOF = 1.0 * 106 h−1 respectively), easy separation, and efficient recycling of the catalyst are the strengths of the present method.

scholarly journals Enzymatic synthesis of hypermodified DNA polymers for sequence-specific display of four different hydrophobic groups

2020 ◽  
Vol 48 (21) ◽  
pp. 11982-11993
Author(s):  
Marek Ondruš ◽  
Veronika Sýkorová ◽  
Lucie Bednárová ◽  
Radek Pohl ◽  
Michal Hocek
Keyword(s):  
Phenyl Group ◽  
High Fidelity ◽  
Dna Duplexes ◽  
Asymmetric Pcr ◽  
Template Strand ◽  
Modified Dna ◽  
Specific Manner ◽  
Dna Backbone ◽  
Modified Oligonucleotide ◽  
Selection Of

Abstract A set of modified 2′-deoxyribonucleoside triphosphates (dNTPs) bearing a linear or branched alkane, indole or phenyl group linked through ethynyl or alkyl spacer were synthesized and used as substrates for polymerase synthesis of hypermodified DNA by primer extension (PEX). Using the alkyl-linked dNTPs, the polymerase synthesized up to 22-mer fully modified oligonucleotide (ON), whereas using the ethynyl-linked dNTPs, the enzyme was able to synthesize even long sequences of >100 modified nucleotides in a row. In PCR, the combinations of all four modified dNTPs showed only linear amplification. Asymmetric PCR or PEX with separation or digestion of the template strand can be used for synthesis of hypermodified single-stranded ONs, which are monodispersed polymers displaying four different substituents on DNA backbone in sequence-specific manner. The fully modified ONs hybridized with complementary strands and modified DNA duplexes were found to exist in B-type conformation (B- or C-DNA) according to CD spectral analysis. The modified DNA can be replicated with high fidelity to natural DNA through PCR and sequenced. Therefore, this approach has a promising potential in generation and selection of hypermodified aptamers and other functional polymers.

scholarly journals Synthesis of Novel, Dual-Targeting 68Ga-NODAGA-LacN-E[c(RGDfK)]2 Glycopeptide as a PET Imaging Agent for Cancer Diagnosis

Pharmaceutics ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 796
Author(s):  
Barbara Gyuricza ◽  
Judit P. Szabó ◽  
Viktória Arató ◽  
Dániel Szücs ◽  
Adrienn Vágner ◽  
...  
Keyword(s):  
Cancer Diagnosis ◽  
Pet Imaging ◽  
Solid Phase ◽  
Click Reaction ◽  
Radiochemical Yield ◽  
Log P ◽  
Αvβ3 Integrin ◽  
Radiolabeled Peptides ◽  
Galectin 3

Radiolabeled peptides possessing an Arg-Gly-Asp (RGD) motif are widely used radiopharmaceuticals for PET imaging of tumor angiogenesis due to their high affinity and selectivity to αvβ3 integrin. This receptor is overexpressed in tumor and tumor endothelial cells in the case of numerous cancer cell lines, therefore, it is an excellent biomarker for cancer diagnosis. The galectin-3 protein is also highly expressed in tumor cells and N-acetyllactosamine is a well-established ligand of this receptor. We have developed a synthetic method to prepare a lactosamine-containing radiotracer, namely 68Ga-NODAGA-LacN-E[c(RGDfK)]2, for cancer diagnosis. First, a lactosamine derivative with azido-propyl aglycone was synthetized. Then, NODAGA-NHS was attached to the amino group of this lactosamine derivative. The obtained compound was conjugated to an E[c(RGDfK)]2 peptide with a strain-promoted click reaction. We have accomplished the radiolabeling of the synthetized NODAGA-LacN-E[c(RGDfK)]2 precursor with a positron-emitting 68Ga isotope (radiochemical yield of >95%). The purification of the labeled compound with solid-phase extraction resulted in a radiochemical purity of >99%. Subsequently, the octanol–water partition coefficient (log P) of the labeled complex was determined to be −2.58. In addition, the in vitro stability of 68Ga-NODAGA-LacN-E[c(RGDfK)]2 was investigated and it was found that it was stable under the examined conditions.

scholarly journals Totally synthetic microperoxidase-11

2018 ◽  
Vol 5 (5) ◽  
pp. 172311 ◽  
Author(s):  
Junichi Tanabe ◽  
Koji Nakano ◽  
Ryutaro Hirata ◽  
Toshiki Himeno ◽  
Ryoichi Ishimatsu ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
High Speed ◽  
Solid Phase ◽  
Click Reaction ◽  
Direct Electron Transfer ◽  
Solid Phase Peptide Synthesis ◽  
Slab Waveguide ◽  
Catalytic Current ◽  
Microscopy Measurement ◽  
Morphological Differences

A totally synthetic microperoxidase-11 (MP-11) is reported. Accordingly, the undecapeptide (VQKCAQCHTVE) was synthesized by solid-phase peptide synthesis followed by the thiol-ene click reaction with haemin for reconstitution. High-speed atomic force microscopy measurement conducted in water confirmed the protein reconstitution by visualizing the morphological differences as animated molecular images. The synthetic MP-11 showed a considerable magnitude of catalytic activity (27%) against the natural MP-11 in the oxidation of 3,3′,5,5′-tetramethylbenzidine by hydrogen peroxide, whereas it showed very low (2.7%) activity of a synthetic variant with a point mutation (VQKCAQC M TVE, H8M). Slab waveguide spectroscopic measurements revealed that the ferrous/ferric redox reaction occurred by the direct electron transfer with specific spectral changes. Indeed, if hydrogen peroxide existed in the solution phase, the peroxidase-modified electrode showed catalytic current–voltage behaviour regardless of whether it was prepared using natural MP-11 or the synthetic MP-11. If a substrate recycling reaction was assumed, computer simulation well reproduced the experimental curves to give a global set of electrocatalytic reaction parameters. In any of the experiments, the synthetic MP-11 and natural MP-11 gave almost identical results. Our approach will be a convenient means of preparing MP-11, as well as its mutants, that does not rely on nature.

Synthesis of Modified DNA by PCR with Alkyne-Bearing Purines Followed by a Click Reaction

2008 ◽  
Vol 10 (2) ◽  
pp. 249-251 ◽  
Author(s):  
Philipp M. E. Gramlich ◽  
Christian T. Wirges ◽  
Johannes Gierlich ◽  
Thomas Carell
Keyword(s):  
Click Reaction ◽  
Modified Dna

scholarly journals Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: a backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography

2019 ◽  
Vol 10 (47) ◽  
pp. 10948-10957 ◽  
Author(s):  
Patrick F. Conlon ◽  
Olga Eguaogie ◽  
Jordan J. Wilson ◽  
Jamie S. T. Sweet ◽  
Julian Steinhoegl ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Tertiary Structure ◽  
Solid Phase ◽  
Phase Synthesis ◽  
X Ray ◽  
Structural Characterisation ◽  
X Ray Crystallography ◽  
Modified Dna

Stable selenium-modified DNA which maintains the native tertiary structure has been prepared under automated conditions enabling SAD X-ray crystallography.

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