scholarly journals Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

2014 ◽  
Vol 10 ◽  
pp. 2279-2285 ◽  
Author(s):  
Alejandro Gimenez Molina ◽  
Amit M Jabgunde ◽  
Pasi Virta ◽  
Harri Lönnberg
Keyword(s):  
Building Block ◽  
Rna Synthesis ◽  
Building Blocks ◽  
Solution Phase ◽  
Dipolar Cycloaddition ◽  
Proof Of Concept ◽  
Phase Synthesis ◽  
Solution Phase Synthesis ◽  
High Yields

An effective method for the synthesis of short oligoribonucleotides in solution has been elaborated. Novel 2'-O-(2-cyanoethyl)-5'-O-(1-methoxy-1-methylethyl) protected ribonucleoside 3'-phosphoramidites have been prepared and their usefulness as building blocks in RNA synthesis on a soluble support has been demonstrated. As a proof of concept, a pentameric oligoribonucleotide, 3'-UUGCA-5', has been prepared on a precipitative tetrapodal tetrakis(4-azidomethylphenyl)pentaerythritol support. The 3'-terminal nucleoside was coupled to the support as a 3'-O-(4-pentynoyl) derivative by Cu(I) promoted 1,3-dipolar cycloaddition. Couplings were carried out with 1.5 equiv of the building block. In each coupling cycle, the small molecular reagents and byproducts were removed by two quantitative precipitations from MeOH, one after oxidation and the second after the 5'-deprotection. After completion of the chain assembly, treatment with triethylamine, ammonia and TBAF released the pentamer in high yields.

scholarly journals Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

2017 ◽  
Vol 13 ◽  
pp. 919-924 ◽  
Author(s):  
Yuta Isoda ◽  
Norihiko Sasaki ◽  
Kei Kitamura ◽  
Shuji Takahashi ◽  
Sujit Manmode ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Building Blocks ◽  
Solution Phase ◽  
Protecting Groups ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block.

Solution-phase synthesis of novel Δ2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties

2003 ◽  
Vol 11 (21) ◽  
pp. 4539-4544 ◽  
Author(s):  
Basappa ◽  
M.P. Sadashiva ◽  
K. Mantelingu ◽  
S.Nanjunda Swamy ◽  
K.S. Rangappa
Keyword(s):  
Solution Phase ◽  
Dipolar Cycloaddition ◽  
Phase Synthesis ◽  
Antifungal Properties ◽  
Solution Phase Synthesis

scholarly journals Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks

2015 ◽  
Vol 11 ◽  
pp. 1553-1560 ◽  
Author(s):  
Amit M Jabgunde ◽  
Alejandro Gimenez Molina ◽  
Pasi Virta ◽  
Harri Lönnberg
Keyword(s):  
Disulfide Bond ◽  
Building Blocks ◽  
Reductive Cleavage ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

The preparation of a disulfide-tethered precipitative soluble support and its use for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks is described. To obtain the building blocks, N-acyl protected 2´-deoxy-5´-O-(4,4´-dimethoxytrityl)ribonucleosides were phosphorylated with bis(benzotriazol-1-yl) 2-chlorophenyl phosphate. The “outdated” phosphotriester strategy, based on coupling of PV building blocks in conjunction with quantitative precipitation of the oligodeoxyribonucleotide with MeOH is applied. Subsequent release of the resulting phosphate and base-protected oligodeoxyribonucleotide trimer 3’-pTpdCBzpdGibu-5’ as its 3’-(2-chlorophenyl phosphate) was achieved by reductive cleavage of the disulfide bond.

scholarly journals Solution Phase Synthesis and Workup Using an Integrated Approach

2003 ◽  
Vol 8 (2) ◽  
pp. 41-43
Author(s):  
Lewin T. Wint ◽  
Marija Kovacevic ◽  
Matt Waters ◽  
Mettler-Toledo AutoChem
Keyword(s):  
Organic Synthesis ◽  
Integrated Approach ◽  
Building Blocks ◽  
Solution Phase ◽  
Automated System ◽  
Automated Systems ◽  
Time Saving ◽  
Phase Synthesis ◽  
Drug Candidates ◽  
Solution Phase Synthesis

Traditional organic synthesis is often cumbersome and time consuming. Significant effort by manufacturers of automated systems has been directed at increasing the speed, efficiency, and consistency of performing chemical reactions. To date, the numbers of integrated systems that combine all the relevant steps of compound preparation are few. Using the five automated systems in tandem can successfully streamline research and development of potential drug candidates. The features of these workstations offer a unique approach for supporting the convenient synthesis and workup of diverse compounds without compromising reagent types or conditions used for synthesis. This poster details an example of the automated drug discovery approach to high throughput organic synthesis using the solution phase synthesis of a series of 1-indanones as building blocks and subsequent reductive amination reactions to generate a diverse group of amines. The purpose of each automated system is outlined along with its role in generating the small library as an illustration of the importance of time saving devices in laboratories.

Solution-phase synthesis and biological evaluation of triostin A and its analogues

2016 ◽  
Vol 14 (6) ◽  
pp. 2090-2111 ◽  
Author(s):  
Kozo Hattori ◽  
Kota Koike ◽  
Kensuke Okuda ◽  
Tasuku Hirayama ◽  
Masahiro Ebihara ◽  
...  
Keyword(s):  
Cell Proliferation ◽  
Biological Evaluation ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Total Syntheses ◽  
Solution Phase Synthesis ◽  
Triostin A ◽  
Inhibitory Activities ◽  
High Yields ◽  
Synthesis And Biological Evaluation

We have accomplished preparative solution-phase total syntheses of triostin A (17.5% in 13 steps) and its analogues with high yields to demonstrate their significant inhibitory activities on HIF-1 activation and cell proliferation.

Synthesis of Casein-Related Peptides and Phosphopeptides. I. Solution-Phase Synthesis and 13C N.M.R.-Spectroscopy of the N-α-Acetyl Octapeptide N-Methylamide Corresponding to Region 14-21 of Bovine β-Casein A2

1987 ◽  
Vol 40 (2) ◽  
pp. 257 ◽  
Author(s):  
JW Perich ◽  
PF Alewood ◽  
RB Johns
Keyword(s):  
Solution Phase ◽  
Phase Method ◽  
Peptide Fragments ◽  
Mixed Anhydride ◽  
Phase Synthesis ◽  
Solution Phase Synthesis ◽  
Coupling Procedure ◽  
Fragment Condensation ◽  
High Yields ◽  
Solution Phase Method

The octapeptide, Ac-Glu-Ser-Leu-Ser-Ser-Ser-Glu-Glu-NHMe (I), was synthesized by the solution-phase method by using the mixed anhydride coupling procedure for the fragment condensation of the Nα-acetyl tripeptide, Ac-Glu(OBut)-Ser(But)-Leu-OH, with the pentapeptide N-methylamide hydrochloride, Cl.H2-Ser(But)-Ser(But)-Ser(But)-Glu(OBzl)-Glu(OBzl)-NHMe, followed by palladium-catalysed hydrogenolysis of Ac-Glu(OBut)-Ser(But)-Leu-Ser(But)-Ser(But)- Ser(But) Glu(OBzl)Glu(OBzl NHMe in trifluoroacetic acid. The synthesis of the two peptide fragments was accomplished in high yields and purity by using the repetitive excess mixed anhydride procedure and the isobutoxycarbonyl mixed anhydride of acetic acid for the rapid and high yielding N-acetylation of the tripeptide fragment. 13C n.m.r. spectroscopy was routinely used to monitor the efficiency of the coupling steps and to confirm the structure of octapeptide (1), signal assignments being possible for both the protected tri- and penta-peptides.

A Low Temperature, Solution Phase Synthesis of III-V Semiconductor Nanocrystals

1994 ◽  
Vol 351 ◽  
Author(s):  
Shreyas S. Kher ◽  
Richard L. Wells
Keyword(s):  
Semiconductor Nanocrystals ◽  
Solution Phase ◽  
High Yield ◽  
Group V ◽  
Phase Synthesis ◽  
Group Iii ◽  
Wide Range ◽  
Solution Phase Synthesis ◽  
Temperature Solution ◽  
High Yields

ABSTRACTNanocrystalline materials have been intensely investigated in the recent past due to the novel properties associated with size-quantized particles. We have developed a new method for high yield, solution phase synthesis of nanocrystalline III-V semiconductors which eliminates the use of substituted or unsubstituted Group V hydrides and Group III alkyls. Our approach consists of in situ syntheses of (Na/K)3E (E = P, As, Sb) in aromatic solvents and subsequent reactions of these pnictides with Group III halide solutions in coordinating solvents. The nanocrystalline III-V semiconductors GaP, GaAs, GaSb, InP, InAs and InSb are readily prepared in a wide range of particle sizes (4–36 nm) and in high yields. The resultant Ill-V materials have been characterized by XRD, EDXA, TEM and elemental analyses.

Synthesis of Yolk-Shell Co3O4/Co1-xRuxO2 Microspheres Featuring an Enhanced Electrocatalytic Oxygen Evolution in Acidic Medium

2021 ◽  
Author(s):  
Abinaya Annamalai ◽  
Dipak Vijaykumar Shinde ◽  
Joka Buha ◽  
Sergio Marras ◽  
Mirko Prato ◽  
...  
Keyword(s):  
Water Splitting ◽  
Oxygen Evolution ◽  
Acidic Medium ◽  
Building Blocks ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Hollow Structures ◽  
Solution Phase Synthesis ◽  
Electrochemical Water Splitting

Hollow structures made of nanoscale building blocks are of great interest as catalysts for electrochemical water splitting. Here we report a solution-phase synthesis of yolk-shell Co3O4/Co1-xRuxO2 microspheres (MSs) having a...

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