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Metkinen Chemistry focuses on research and manufacture of reagents for RNA and DNA synthesis. We have expert knowledge of nucleoside chemistry, reagents for oligonucleotide synthesis, phosphoramidites and various solid supports. Reagents for oligo synthesis product line include Truly Universal solid support, Chemical Phosphorylation Reagent and Trimer (codon) Phosphoramidites. Possible applications encompass combinatorial oligonucletide libraries with trimer (codon) phosphoramidites, oligo synthesis using our Truly Universal solid support and convenient purification of oligonucleotide 5'-phosphates with Chemical Phosphorylation Reagent. Today the efforts of Metkinen Chemistry are concentrated on our extensive line of purine nucleosides. Ultra-pure purine nucleoside analogs are used in the development of oligonucleotide therapeutics and in research applications. The new products, namely 3'- Amino-2',3'-dideoxy-A and G nucleosides serve as building blocks for oligonucleotides that are resistant to enzymatic degradation. Another set of new nucleosides - 2'-deoxy-2'-fluoro-A and G, as well as 2'-deoxy-2'-amino-A and G are popular building clocks for the stabilization of small interfering RNAs (siRNAs) and aptamers. Metkinen Chemistry's biotransformation technology addresses the problems of traditional synthetic methods and offers alternative variants of biotransformation. Our flexibility and expertise allow Metkinen Chemistry to cater to a range of customer needs: from one-off oligonucleotide synthesis in academia to large-scale commercial production. Naturally this is reflected in appropriate discounts applied according to order size.
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Synthetic RNA oligonucleotides, incorporating 2'-Deoxy-2’-fluoro-nucleosides (2’-F-RNA) find constantly increasing applications in research and new drug development. Among important areas of their application are such as design and synthesis of efficient and stable siRNAs, aptamers, anti-microRNAs (Antagomirs) as well as general use for affinity purification of RNA-binding proteins.
Today Metkinen Chemistry offers more than 99% pure purine 2’-fluoronucleosides, prepared by bioconversion of synthetic 2’-F-uridine, using evolved recombinant E.coli strains. These strains, in turn are grown on the media, incorporation only ingredients, derived from yeast and vegetable. That means that in the production process no secondary reagents of animal source (either BSE certified or non- BSE certified) are employed at any stage of 2’-F- A and G preparation. Hence, we guarantee the complete absence of ANY BSE/TSE risk, associated with our 2’-F-nucleosides and derivatives.
In addition to purine 2’-F-nucleosides, we offer a full set of 2’-F-nucleoside CE-phosphoramidites for chemical synthesis and a full set of 2’-F-nucleoside 5’-triphosphates for enzymatic preparation of 2’-F-RNA. Our latest addition to series of 2’-fluoronucleoside derivatives – 2’-F-nucleoside bound solid supports for 2’-F-RNA oligosynthesis, complements the range of these compounds and opens up a full spectrum of 2’-F-RNA applications. 2'-Fluoro modifications consistently provided increased target binding affinity, endonuclease stability, and, importantly, reduced immune response. In addition, it is the only modification compared to other carbohydrate modifications, including locked nucleic acid, or LNA, that preserves RISC activity when used in both sense and antisense strands.
2’-Fluoro-2’-deoxyguanosine
2’-Fluoro-2’-deoxyadenosine
2’-Fluoro-2’-deoxyguanosine-3’-CE-phosphoramidite
2’-Fluoro-2’-deoxyadenosine-3’-CE-phosphoramidite
2’-Fluoro-2’-deoxyuridine-3’-CE-phosphoramidite
2’-Fluoro-2’-deoxycytidine-3’-CE-phosphoramidite
2’-Fluoro-2’-deoxynucleoside-5’-triphosphates
2’-F-Nucleoside bound Solid Supports (F-CS-supports)
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2’-Fluoroaraninooligonucleotides (FANA) can be used as antisense oligonucleotides, siRNA and aptamers. Today Metkinen Chemistry offers synthetically synthesized pyrimidine 2’-fluoroarabinonucleosides as well as purine 2’- fluoroarabinonucleosides, prepared by bioconversion of synthetic 2’-F-arabinouridine, employing propriarory evolved recombinant E.coli strains. We guarantee the complete absence of ANY BSE/TSE risk, associated with our 2’-F- fluoroarabinonucleosides.
Metkinen Chemistry offers a full set of 2’-F-nucleoside CE-phosphoramidites for the chemical synthesis and a full set of 2’-F-nucleoside 5’-triphosphates for enzymatic preparation of FANA.
9-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)adenine (FANA-A)
9-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)-2,6-diaminopurineriboside (FANA-DAP)
9-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)guanine (2’-FANA-G)
9-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)hypoxantine (2’-FANA-I)
1-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)cytosine (2’-FANA-C)
1-(2-Fluoro-2-deoxy-ß-D-arabinofuranosyl)uracil (2’-FANA-U)
2'-Fluoro-2'-deoxyarabinonucleosides 5'-triphosphates, tetra Lithium salts
2'-Fluoro-2'-deoxyarabinoadenosine-3'-CE-phosphoramidite
2'-Fluoro-2'-deoxyarabinoguanosine-3'-CE-phosphoramidite
2'-Fluoro-2'-deoxyarabinouridine-3'-CE-phosphoramidite
2'-Fluoro-2'-deoxyarabinocytidine-3'-CE-phosphoramidite
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Analogues of Purine nucleosides have potential interest in antiviral research and are indispensable tools in Molecular biology. They are building blocks for the synthesis of pharmaceutical oligonucleotide analogues and initial compounds for preparation of corresponding nucleoside 5'-di- and triphosphates.
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2’-Amino-2’-deoxyadenosine
2'-Amino-2'-deoxy-2-fluoroadenosine
2’-Amino-2’-deoxy-2,6-diaminopurineriboside
2’-Amino-2’-deoxyguanosine
2’-Amino-2’-deoxyinosine
Arabinofuranosyl-adenine (adenine arabinoside, ara-A)
Arabinofuranosyl-6-Benzylaminopurine (6-Benzylaminopurine arabinoside)
Arabinofuranosyl-2,6-diaminopurine (2,6-diaminopurine arabinoside)
Arabinofuranosyl-2-fluoroadenine
Arabinofuranosyl-guanine (guanine arabinoside, ara-G)
Arabinofuranosyl-isoguanine
6-Benzylaminopurine 2'-deoxyriboside
2-Chloro-2'-deoxyadenosine (2-CdA, cladribine)
2'-Deoxy-2-fluoroadenosine
2’-Fluoro-2’-deoxy-2-fluoroadenosine
2’-Fluoro-2’-Deoxy-2,6-Diaminopurineriboside
2’-Fluoro-2’-Deoxyinosine
2'-Deoxyisoguanosine
2'-Deoxy-2'-fluoroisoguanosine
2,6-Diaminopurine 2'-deoxyriboside
Isoguanosine
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5’-Fluorescein phosphoramidite (6-FAM)
5'-Fluorescein phosphoramidite (5-FAM)
Fluorescein phosphoramidite (I)
Fluorescein phosphoramidite (II)
6-Fluorescein dT phosphoramidite
5-Fluorescein dT phosphoramidite
3'-(6-Fluorescein)-CPG
3'-(5-Fluorescein)-CPG
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Dendrimers are highly branched polymers that possess patterns similar to the branching of trees. Plain and mixed oligonucleotide dendrimers can be synthesized using trebling phosphoramidite synthon.
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Long Trebler Phosphoramidite
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Alkyne amidite, 5’-terminal
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Alkylacetylene phosphoramidite ACH (cryst.)
Alkylacetylene phosphoramidite LC
6-TAMRA-CEP
6-JOE-dT-CEP
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Metkinen Universal Support is appropriate for the production of DNA and RNA and modified oligonucleotides from laboratory to industrial scale. It requires fast and mild cleavage conditions. Chemical Phosphorylation Reagent allows convenient purification of oligonucleotide 5'-phosphates by the straightforward DMTr-on technique. Trinucleotide and Dinucleotide phosphoramidite building blocks are reagents of choice for generation of highly randomized DNA sequences. These sequences may incorporate 20 codons, corresponding to all natural amino acids.
Metkinen Chemistry uses proprietary technology for production of some reagents for DNA and RNA synthesis. The invention (CATAPAZ chemistry) relates to highly efficient and straightforward carbamoylation of amines, mercaptanes, thiophenols and some alcohols employing organic azides, triphenylphosphine or polymer bound triphenylphosphine along with aqueous hydrogen carbonate buffer.
At present, the CATAPAZ chemistry is successfully used for the production of Universal solid support (USIII) and new nucleoside bound supports (CS) for synthesis of DNA, RNA, siRNA as well as any type of modified oligonucleotides. Development of new products for oligonucleotide synthesis, that are prepared employing the CATAPAZ chemistry is now in progress. The Catapaz PCT application has now been published with No. WO 2008/049972. Please follow the link to see patent description.
Comprehensive coverage of CATAPAZ technology and application can be
found in the following article "Straightforward carbamoylation of nucleophilic compounds employing
organic azides, phosphines, and aqueous trialkylammonium hydrogen carbonate" by Andrey Yagodkin, Kerstin Loschcke, Janne Weisell and Alex Azhayev published in Tetrahedron. Please follow the link to see the article.
Metkinen Universal Solid Support
Chemical Phosphorylation Reagent II
Trinucleotide (TRIMER CODON) Phosphoramidites
Dimer Phosphoramidites
2’-Deoxynucleoside bound Solid Supports (CS-supports)
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Modified Nucleoside 5’-triphosphates are popular products for various applications: PCR, DNA- and RNA-polymerase, reverse transcriptase based assays, etc. Nowadays these compounds find diverse use in siRNA and Aptamer research.
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2'-Deoxy-2,2'-difluoroadenosine 5’-triphosphate, tetra-lithium salt
2'-Deoxy-2-fluoroadenosine 5’-triphosphate, tetra-lithium
2-Fluoro-9-ß-D-arabinofuranosyladenine 5’-triphosphate, tetra-lithium salt
2'-Deoxy-2-chloroadenosine 5’-triphosphate, tetra-lithium salt
6-Benzylamino-2'-deoxy-9-ß-D-ribofuranosylpurine 5’-triphosphate, tetra-lithium salt
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3'-Amino-2',3' dideoxynucleosides are synthesized via biotransformation and used as initial compounds for preparation of corresponding 3'-Amino-2',3'-Dideoxynucleoside-5'-CE Phosphoramidites. The latter are building blocks for the assembly of Oligonucleotide N3' -> P5' phosphoramidates, that form extremely stable double and triple stranded complexes with DNA and RNA under physiological conditions and appear to be efficient telomerase inhibitors and antisense agents.
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3'-Amino-2',3'-dideoxyadenosine
3'-Amino-2',3'-dideoxyguanosine
3'-Amino-2',3'-dideoxy-2-fluoroadenosine
3'-Amino-2',3'-dideoxy-2,6-diaminopurineriboside
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Biotin-11-UTP
Biotin-11-dUTP
Biotin-11-dCTP
Biotin-11-dATP
Biotin-16-dUTP
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6-FAM-11-dUTP
6-FAM-11-dCTP
6-FAM-11-UTP
FAM-11-dATP
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SIMA phosphoramidite
6-SIMA-dT
5-SIMA phosphoramidite
6-SIMA-CPG
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HEX phosphoramidite
5-HEX phosphoramidite
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TET phosphoramidite
5-TET phosphoramidite
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5'-Biotin Phosphoramidite
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5’-DMS(O)MT-Amino-Modifier-C6
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5-JOE phosphoramidite
6-JOE-dT-CEP
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Pyrene Derivative
Pyrelene Derivative
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Spacer 18 Phosphoramidite
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Reagent 1-amidite
Reagent 3-amidite
Reagent 2-amidite
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