ChemInform Abstract: Solid-Phase Synthesis of Protected Oligonucleotide Blocks. Applications to Block Condensation on a Polymer Support and Synthesis of a 3′-Modified Oligonucleotide.

ChemInform ◽  
1987 ◽  
Vol 18 (20) ◽  
Author(s):  
S. IWAI ◽  
M. KOIZUMI ◽  
M. IKEHARA ◽  
E. OHTSUKA
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Polymer Support ◽  
Phase Synthesis ◽  
Modified Oligonucleotide

scholarly journals Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1872 ◽  
Author(s):  
Ondřej Kostov ◽  
Radek Liboska ◽  
Ondřej Páv ◽  
Pavel Novák ◽  
Ivan Rosenberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Novel ◽  
Phase Synthesis ◽  
Chimeric Oligonucleotides ◽  
Modified Oligonucleotide

We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands.

scholarly journals Optimal Method for Disulfide Bond Closure in the Synthesis of Atosiban—Antagonist of Oxytocin Receptors

2021 ◽  
Vol 47 (6) ◽  
pp. 1241-1248
Author(s):  
D. V. Avdeev ◽  
M. V. Ovchinnikov ◽  
Y. S. Dudkina ◽  
A. S. Molokoedov ◽  
A. A. Azmuko ◽  
...  
Keyword(s):  
Disulfide Bond ◽  
Large Scale ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Comparative Assessment ◽  
Polymer Support ◽  
Optimal Method ◽  
Phase Synthesis ◽  
Oxytocin Receptors ◽  
By Products

Abstract This work is devoted to the large-scale solid-phase synthesis (SPS) of Atosiban, Mpa1-D-Tyr(OEt)-Ile-Thr-Asn-Cys6-Pro-Orn-Gly-NH2 cyclic 1,6 disulfide, the only clinically used oxytocin receptor antagonist. The conditions have been selected for the closure of the disulfide bond (S–S) in the Atosiban molecule both in the solution and solid phase with the minimal formation of by-products. A comparative assessment of the formation of the S–S bond was carried out under various conditions. The formation of by-products during the closure of the disulfide bond has been studied both in solution and on the polymer support. The developed technique allows for the synthesis of Atosiban on an enlarged scale (10–20 mmol) involving the cyclization of a protected intermediate with the formation of the S–S bond during solid-phase synthesis with the minimal formation of by-products.

Solid-phase Synthesis of Phosphorus Derivatives

2019 ◽  
Vol 23 (6) ◽  
pp. 679-688
Author(s):  
Vasile Simulescu ◽  
Gheorghe Ilia
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Condensation Reaction ◽  
Solid Polymer ◽  
Polymer Support ◽  
Phase Method ◽  
Phase System ◽  
Covalent Bonds ◽  
Phase Synthesis ◽  
Whole Process

The solid-phase synthesis (SPS) of phosphorus-containing compounds is based mainly on the fact that the chemical process is conducted in a two-phase system. One of the components is connected via covalent bonds to a solid support, which is in general an insoluble polymer, representing the solid phase of the process. The other components involved into the process are solubilized in a solution. The method is suitable to be applied to almost any organic compounds. A common example of using solid-phase synthesis is for obtaining products nucleotide containing, similar to nucleic acids. During the whole process, the nucleotide is always on the solid phase, after the condensation reaction, except for the last step, when the synthesis is already finished. Then, the product is released and separated very easily by filtration. The obtained polymer-oligonucleotide product can participate further in condensation reactions as well. Other important biomolecules synthesized by solid-phase approach during the last decades are nucleoside di- and triphosphates, nucleoside diphosphate sugars and dinucleoside polyphosphates. Those products are precursors of deoxysugars, aminodeoxysugars, uronic acids or glycoconjugates, and are also necessary for DNA and RNA synthesis. The use of the solid-phase method in the context of immobilized oligomers is of great interest nowadays. The solid-phase synthesis offers many advantages in comparison with the conventional solution-phase method, because it takes much less time, it is highly stereoselective, the products are separated and purified usually by a simple filtration or decantation, solvents with high boiling points could be used, the whole process is based on solid polymer support and the obtained compounds should not be isolated.

scholarly journals Studies on peptides. CXLIX Solid-phase synthesis of a rabbit stomach peptide by application of a new polymer support and a new deprotecting procedure.

1987 ◽  
Vol 35 (3) ◽  
pp. 1266-1269 ◽  
Author(s):  
NOBUTAKA FUJII ◽  
YOSHIO HAYASHI ◽  
KENICHI AKAJI ◽  
SUSUMU FUNAKOSHI ◽  
MASAHARU SHIMAMURA ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Polymer Support ◽  
Phase Synthesis

The Boc/Solid Phase Synthesis of Glu-Abu(P)-Leu

1992 ◽  
Vol 45 (10) ◽  
pp. 1765 ◽  
Author(s):  
JW Perich ◽  
EC Reynolds
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydrogen Bromide ◽  
Solid Phase Peptide Synthesis ◽  
Polymer Support ◽  
Methyl Groups ◽  
Phase Synthesis

The synthesis of the 4-phosphono-2-aminobutanoyl-containing tripeptide , H- Glu -Abu(P)- Leu-OH.CF3C02H was accomplished by the use of Boc-Abu(PO3Me2)-OH in Boc /solid phase peptide synthesis. Peptide synthesis was performed by using Boc-Leu-polystyrene as the polymer support with the peptide assembled by the use of 1H-benzotriazol-1-yloxytris(pyrro1idin-1-yl) phosphonium hexafluorophosphate ( PyBOPR ) for the coupling of Boc amino acids and 50% CF3C02H/CH2C12 for cleavage of the Boc group from the Boc -peptide after each coupling cycle. The protected peptide was cleaved from the polymer support by hydrogen bromide in trifluoroacetic acid and final cleavage of the methyl groups from Glu-Abu(PO2Me2)-Leu was effected by silylitic treatment with 30% bromotrimethylsilane in acetonitrile.

scholarly journals Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4266 ◽  
Author(s):  
Mariya I. Meschaninova ◽  
Darya S. Novopashina ◽  
Olga A. Semikolenova ◽  
Vladimir N. Silnikov ◽  
Alya G. Venyaminova
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Polymer Support ◽  
Phase Synthesis ◽  
Wide Range ◽  
Different Types ◽  
Convenient Approach ◽  
Aliphatic Diamines ◽  
Oligonucleotide Conjugates ◽  
Derivatives Of

A novel and convenient approach for the solid-phase 5′-functionalization of oligonucleotides is proposed in this article. The approach is based on the activation of free 5′-hydroxyl of polymer support-bound protected oligonucleotides by N,N′-disuccinimidyl carbonate followed by interaction with amino-containing ligands. Novel amino-containing derivatives of closo-dodecaborate, estrone, cholesterol, and α-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, α-tocopherol, folate, estrone), aliphatic diamines, and propargylamine were synthesized and characterized to demonstrate the versatility of the approach. The developed method is suitable for the conjugate synthesis of oligonucleotides of different types (ribo-, deoxyribo-, 2′-O-methylribo-, and others).

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