Synthesis of nucleosides. Medical search. Frequent questions

Nucleoside polyphosphates and their conjugates, such as nucleoside triphosphates, nucleoside tetraphosphates, sugar nucleotides, dinucleoside pyro- and higher order polyphosphates, 2',3'-cyclic nucleoside monophosphates, and 2´-deoxynucleoside-5´-tetraphosphates in which a fluorescent label is attached to the terminal phosphate have many biological roles and have been developed into drugs. (uwaterloo.ca)
These agents behave as antimetabolites that interact with a number of intracellular targets blocking the DNA chain elongation or interfering with biosynthesis of nucleosides and nucleotides, a limiting process in cell proliferation. (unicam.it)
These are basically of two types, ribonucleic (RNA) and deoxyribonucleic (DNA) acids, both of which consist of nucleotides (nucleoside phosphates linked together by phosphate bridges). (bvsalud.org)

The silyl-Hilbert-Johnson (or Vorbrüggen) reaction, which employs silylated heterocyclic bases and electrophilic sugar derivatives in the presence of a Lewis acid, is the most common method for forming nucleosides in this manner. (wikipedia.org)
Stereoselective synthesis of deoxyribonucleosides directly from deoxyribose derivatives is more difficult to achieve because neighboring group participation cannot take place. (wikipedia.org)
This section describes both derivatives of and alternatives to the SHJ reaction that are used for the synthesis of nucleosides. (wikipedia.org)

The importance of nucleoside analogues in a number of areas of drug discovery and chemical biology continues to act as a spur to develop practical and efficient synthetic methods for accessing these compounds. (thieme.de)
Nucleoside analogues are a pharmacologically diverse family that includes cytotoxic compounds, antiviral agents and immunosuppressive molecules. (unicam.it)

Nucleoside reverse transcriptase inhibitors (NRTIs) have been reported to be beneficial in preventing cytoplasmic DNA synthesis. (genengnews.com)
Nucleoside reverse transcriptase inhibitors (NRTIs) are phosphorylated to active metabolites that compete for incorporation into viral DNA. (msdmanuals.com)
Non-nucleoside reverse transcriptase inhibitors (NNRTIs) bind directly to the reverse transcriptase enzyme. (msdmanuals.com)

Nucleosides are typically synthesized through the coupling of a nucleophilic pyrimidine, purine, or other basic heterocycle with a derivative of ribose or deoxyribose that is electrophilic at the anomeric carbon. (wikipedia.org)
7) Transglycosylation, which involves the reversible transfer of a sugar moiety from one heterocyclic base to another, is effective for the conversion of pyrimidine nucleosides to purine nucleosides. (wikipedia.org)
Pyrimidine nucleoside phosphorylase from Bacillus subtilis (BsPyNP, E.C. 2.4.2.3) and thymidine phosphorylase from Escherichia coli (EcTP, E.C. 2.4.2.4) were used, as immobilized enzymes, in the synthesis of 5-halogenated pyrimidine 2′-deoxyribonucleosides (14-18) by transglycosylation in fully aqueous medium. (unimib.it)

Deoxy-ATP (dATP) can reach toxic levels that inhibit ribonucleotide reductase, an enzyme essential for synthesis of DNA precursors. (medscape.com)
Purine nucleoside phosphorylase is a ubiquitously expressed enzyme of the purine salvage pathway as is adenosine deaminase, deficiency of which also causes immunodeficiency. (frontiersin.org)
Researchers from TU Graz and acib succeed in the first enzyme-driven biocatalytic synthesis of nucleic acid building blocks. (tugraz.at)
Bernd Nidetzky, Head of the Institute of Biotechnology and Bioprocess Engineering at TU Graz and at the same time Scientific Director of the Austrian Centre of Industrial Biotechnology (acib), and Martin Pfeiffer from acib discovered and characterized in a study the enzyme 'YeiN', which can link the two nucleoside building blocks ribose-5-phosphates and uracil by means of a specific carbon bond. (tugraz.at)
They are the first researchers worldwide to demonstrate an enzyme that is a suitable biocatalyst for the production of C-nucleosides. (tugraz.at)
5-FdUMP inhibits thymidylate synthase (key enzyme in DNA synthesis), which leads to accumulation of dUMP, which then gets misincorporated into the DNA in the form of 5-FdUTP resulting in inhibition of DNA synthesis and function with cytotoxic DNA strandbreaks. (medscape.com)
What is the function of the NDPK enzyme in nucleotide synthesis? (lecturio.de)
They inhibit the HIV reverse transcriptase enzyme competitively and terminate synthesis of DNA chains. (msdmanuals.com)

The C-nucleoside based drug Remdesivir has these necessary antiviral properties and is effective against a number of RNA viruses, including corona and ebola viruses. (tugraz.at)
We previously described the synthesis of 1-O-octadecyl-2-O-benzyl-glycero-3-phospho-RVn (V2043), an orally bioavailable lipid prodrug of remdesivir nucleoside (RVn, GS-441524) with broad spectrum antiviral activity against viruses with pandemic potential. (cdc.gov)

Finally an entirely new approach to the synthesis of nucleoside tetraphosphates (Np4's), dinucleoside pentaphosphates (Np5N's) and nucleoside tetraphosphates in which a fluorescent dye is attached to the terminal phosphate is described employing an activated form of cyclic trimetaphosphate as a novel phosphorylating agent. (uwaterloo.ca)
Optimization of 5-fluoro-2′-deoxyuridine (14) synthesis (pH 7.5, 10 mM phosphate buffer, nucleoside/nucleobase 3:1 molar ratio) and subsequent scale-up afforded the target compound in 73% (EcTP) or 76% (BsPyNP) conversion (about 9 g/L). (unimib.it)

In recent years, several nucleoside RNR inhibitors have entered clinical trial or application such as arabinosylcytosine (ara-C), gemcitabine, cladribine, fludarabine and clofarabine. (unicam.it)

Several novel and efficient approaches to the synthesis of nucleoside polyphosphates and their conjugates were developed. (uwaterloo.ca)
The procedure is rapid, produces a wide variety of nucleoside polyphosphates and their conjugates in high yield, does not require protection and subsequent deprotection of the nucleotide donors or acceptors and can be used to activate nucleoside mono-, di-, and triphosphates and a wide variety of acceptors. (uwaterloo.ca)
A representative set of Cbz-protected ( α -aminoxyacyl)benzotriazoles was utilized as versatile building blocks for the efficient and convenient synthesis of novel α -aminoxy acid conjugates. (rsc.org)

Which of the following is true regarding purine synthesis? (lecturio.de)
MZB has a very specific mechanism of action on the lymphocytes that inhibits their proliferation without interfering with purine synthesis in other cell types. (hindawi.com)

The synthesis and base pairing properties of platinum complexes based on uridine and deoxyuridine nucleosides and preliminary studies of their antiproliferative activity are described. (bvsalud.org)
Deoxyuridine nucleosides embodied into diarylethenes form an especial class of photoswitchable compounds that are designed to stack and pair with DNA bases. (jascoinc.com)

[ 2 , 3 ] One disorder is adenosine deaminase (ADA) deficiency, which is Online Mendelian Inheritance in Man (OMIM) subject number 102700, and the other is purine nucleoside phosphorylase (PNP) deficiency, which is OMIM subject number 164050. (medscape.com)
In purine nucleoside phosphorylase deficiency, similar changes occur, resulting in elevated deoxy-GTP (dGTP) levels. (medscape.com)
In both adenosine deaminase and purine nucleoside phosphorylase deficiencies, thymocytes are thought to be selectively destroyed because of elevated levels of dATP and dGTP. (medscape.com)
In a further description of the mechanism of T-cell depletion in purine nucleoside phosphorylase deficiency, Arpaia et al reported increased in vivo apoptosis of T cells and increased in vitro sensitivity to gamma irradiation in a murine model. (medscape.com)
[ 4 ] The immune deficiency in purine nucleoside phosphorylase deficiency may be the result of inhibited mitochondrial DNA repair due to the accumulation of dGTP in the mitochondria. (medscape.com)
Purine nucleoside phosphorylase (PNP) deficiency, a rare autosomal recessive metabolic disease causes combined immunodeficiency and developmental delay, hypotonia, and spasticity. (frontiersin.org)
Purine nucleoside phosphorylase (PNP) deficiency (OMIM 613179) is a rare autosomal recessive metabolic disease leading to combined immunodeficiency and neurological abnormalities, which may include developmental delay, hypotonia, and spasticity ( 1 , 2 ). (frontiersin.org)

Sugar-modified bicyclic nucleosides have drawn the attention of synthetic chemists because of their effect on the conformational restriction of the furanose moiety of the nucleoside [1-9] . (beilstein-journals.org)
The conformational restriction has led to the enhancement in target selectivity and in vivo stability of the nucleoside-based drug candidates. (beilstein-journals.org)

2) The silyl-Hilbert-Johnson (SHJ) reaction (or Vorbrüggen reaction), the mildest general method for the formation of nucleosides, is the combination of a silylated heterocycle and protected sugar acetate (such as 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose) in the presence of a Lewis acid. (wikipedia.org)
A second reaction of this nucleoside with 1 generates bis(riboside) 3. (wikipedia.org)
The silyl-Hilbert-Johnson reaction is the most commonly used method for the synthesis of nucleosides from heterocyclic and sugar-based starting materials. (wikipedia.org)
The 6-O-NPE group was completely removed in the reaction of triflate nucleoside 15 with CH 3 CO 2 Na/HMPA. (umn.edu)
Upon reaction of derivative 22 with DAST no formation of the desired 3′-fluoro nucleoside 23 was observed, but only decomposition took place. (umn.edu)
Compared to a purely chemical synthesis, this is a much more efficient way, since fewer reaction steps and no toxic chemicals are required. (tugraz.at)

GS-5734 is a monophosphate prodrug of an adenosine nucleoside analog that showed therapeutic efficacy in a non-human primate model of Ebola virus infection. (nih.gov)

Current Chemical Biology aims to publish full-length and mini reviews on exciting new developments at the chemistry-biology interface, covering topics relating to Chemical Synthesis, Science at Chemistry-Biology Interface and Chemical Mechanisms of Biological Systems. (ingentaconnect.com)
In medicinal chemistry, the molecular family of carbon (C)-nucleosides is particularly in demand. (tugraz.at)

Instead nucleoside 2',3'-cyclic phosphates were obtained in good yield with the ribonucleoside substrates. (uwaterloo.ca)

One of the important precursors for the synthesis of different types of bicyclonucleosides is 4- C -hydroxymethyl-1,2- O -isopropylidene-α-D-ribofuranose. (beilstein-journals.org)

Current Chemical Biology covers the following areas: Chemical Synthesis (Syntheses of biologically important macromolecules including proteins, polypeptides, oligonucleotides, oligosaccharides etc. (ingentaconnect.com)

Thus, inhibition of ATP and mtDNA synthesis is sufficient for ARDS amelioration. (lu.se)
The immunosuppressive effect of MZB has been reported to be due to the inhibition of DNA synthesis in the S phase of the cell cycle. (hindawi.com)

Furthermore, the two separated epimers were used for the convergent synthesis of two different types of bicyclic nucleosides, which confirms their synthetic utility. (beilstein-journals.org)
Lipases have been used extensively for the selective manipulation of hydroxy groups present in different sugars and sugar moieties of synthetic or naturally occurring glycosides, nucleosides, etc. (beilstein-journals.org)
Natural and synthetic nucleosides have an antiviral effect and can act as building blocks of ribonucleic acids (RNA). (tugraz.at)

The biological results showed that the structure of 3'-Me-Ado is crucial for the antitumor activity of this type of ribose-modified nucleosides. (unicam.it)

By targeting electron transport chain complex 1 and independently of AMP-activated protein kinase (AMPK) or NF-κB, metformin blocked LPS-induced and ATP-dependent mitochondrial (mt) DNA synthesis and generation of oxidized mtDNA, an NLRP3 ligand. (lu.se)
Myeloid-specific ablation of LPS-induced cytidine monophosphate kinase 2 (CMPK2), which is rate limiting for mtDNA synthesis, reduced ARDS severity without a direct effect on IL-6. (lu.se)

23 The synthesis of chiral di-, tri- and tetrapeptides from amino acids using N -protected-( α -aminoacyl)benzotriazoles in solution phase occurs with complete retention of chirality. (rsc.org)

Phosphoramidites are modified nucleosides used in the chemical synthesis of oligonucleotides. (usp.org)
Due to the COVID 19 pandemic and the associated intensive search for therapeutics and vaccines, the chemical substance class of nucleosides is experiencing an enormous increase in interest. (tugraz.at)
The biocatalytic production of C-nucleosides is therefore a very strong, elegant alternative to classical chemical synthesis and even superior to it in terms of efficiency,' says Bernd Nidetzky. (tugraz.at)
Classic antimetabolite anticancer drug with chemical structure similar to endogenous intermediates or building blocks of DNA or RNA synthesis. (medscape.com)

This represents a new and convenient approach to the synthesis of this class of compounds. (uwaterloo.ca)
The synthesis of compounds 14-18 proceeded at a similar conversion (33-68% for BsPyNP and 25-62% for EcTP, respectively). (unimib.it)

Nucleophilic attack at the anomeric position by the most nucleophilic nitrogen (N1) then occurs, yielding the desired β-nucleoside 2. (wikipedia.org)
5) The most nucleophilic nitrogen can be blocked through alkylation prior to nucleoside synthesis. (wikipedia.org)
These differ from the naturally more frequently occurring nitrogen (N)-nucleosides - the classical building blocks of RNA - in the way the sugar is linked to the so-called nucleic base. (tugraz.at)
Instead of a carbon-nitrogen bond, C-nucleosides have a carbon-carbon bond. (tugraz.at)

When an acyl-protected ribose is employed, selective formation of the β-nucleoside (possessing the S configuration at the anomeric carbon) results from neighboring group participation. (wikipedia.org)
Glycosylation of thymine with protected 1-acetoxy ribose produced 60% of the N1 nucleoside and 23% of the N3 nucleoside. (wikipedia.org)

Because most heterocyclic bases contain multiple nucleophilic sites, site selectivity is an important issue in nucleoside synthesis. (wikipedia.org)
Closely related triazines, on the other hand, react with complete selectivity to afford the N2 nucleoside. (wikipedia.org)

Nucleosides are naturally occurring biological molecules, which are fundamental building blocks of DNA and RNA. (sru.edu)

The findings were published in the journal, Proceedings of the National Academy of Sciences , in an article titled, "Cytoplasmic synthesis of endogenous Alu complementary DNA via reverse transcription and implications in age-related macular degeneration . (genengnews.com)

Heating the blocked nucleoside in Eq. (6) in the presence of a protected sugar chloride provides the nucleoside in 59% yield. (wikipedia.org)
Upon treatment with DAST, 6 was converted into the corresponding 2′-β-fluoro nucleoside 8 in 43% yield. (umn.edu)
This compound was hydrolyzed with Et 3 N/MeOH/H 2 O to give the 2-N-acetyl derivative 18, which was smoothly converted into the desired 3'-α-fluoro-substituted nucleoside 24 in 76% yield. (umn.edu)
USP has developed DNA phosphoramidites reference standards that can help manufacturers identify and control impurity profiles during oligonucleotide synthesis using various analytical techniques, including HPLC, 31 P NMR, GC, and LC-MS. Ultimately these standards may help yield better control over manufacturing process. (usp.org)

Pfizer admitted that during its clinical studies, participants aged 16 years and older received 30 mcg of nucleoside-modified messenger RNA (modRNA) . (republicbroadcasting.org)

Three general methods have been used to synthesize nucleosides from nucleophilic bases and electrophilic sugars. (wikipedia.org)

Compuestos complejos de gran peso molecular que se encuentran en las células vivas. (bvsalud.org)

2023 , 5 , 48-58: "Broadly Applicable Synthesis of Heteroarylated Dithie-no-[3,2-b:2',3'-d]pyrroles for Advanced Organic Materials. (uni-ulm.de)
2023 , 5 , 35-47: „Synthesis and Functionalization of Heteroarylated Dithieno[3,2-b:2',3'-d]pyr-ro-les for Advanced Materials. (uni-ulm.de)

A group of drugs used to treat HIV that block DNA synthesis in the cytoplasm can be repurposed to treat an advanced form of AMD called geographic atrophy (GA), a new study suggests. (genengnews.com)

Synthesis, Base Pairing Properties, and Biological Activity Studies of Platinum(II) Complexes Based on Uracil Nucleosides. (bvsalud.org)
First, the synthesis was performed with protected nucleosides to generate complexes 1 and 2, which were deprotected under basic conditions, affording complexes 3 and 4 in good yields. (bvsalud.org)
The synthesis with the unprotected nucleosides was also performed and provided complexes 3 and 4 effectively. (bvsalud.org)

MZB is a nucleoside of the imidazole class, and was found to have weak antimicrobial activity against Candida albicans , but it proved ineffective against experimental candidiasis [ 1 ]. (hindawi.com)

5-FU inhibits tumor cell growth through at least 3 different mechanisms that ultimately disrupt DNA synthesis or cellular viability. (medscape.com)
tRNAs are essential for cells and their synthesis is under stringent cellular control. (cdc.gov)

The synthesis of the ribo - trihydroxy sugar derivative starting from diacetone-D-glucose led to the formation of an inseparable 1:1 mixture of the required compound and its C-3 epimer, i.e., 4- C- hydroxymethyl-1,2- O -isopropylidene-α-D-xylofuranose [10] . (beilstein-journals.org)
Treatment of the 2′,5′-di-O-trityl nucleoside 7 with CF 3 SO 2 Cl/DMAP in CH 2 Cl 2 , followed by PhCO 2 K/HMPA, afforded the corresponding xylofuranosyl derivative 16 along with 6-O-deprotected nucleoside 19. (umn.edu)

Synthesis of nucleosides involves the coupling of a nucleophilic, heterocyclic base with an electrophilic sugar. (wikipedia.org)
Syntheses of amino-sugar nucleosides and. (ualberta.ca)

This occurs through self-priming and is the first evidence of human DNA synthesis occurring in the cytoplasmic compartment of the cell. (genengnews.com)

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