Synthesis and sequencing of Informational Poly(amino phosphodiester)s

2021 ◽  
Author(s):  
Ian Roszak ◽  
Laurence Oswald ◽  
Abdelaziz AL-OUAHABI ◽  
Annabelle Bertin ◽  
Eline Laurent ◽  
...  

Sequenced-defined poly(amino phosphodiester)s containing main-chain tertiary amines were synthesized by automated solid-phase phosphoramidite chemistry. These polymers were prepared using four monomers with different substituents. The formed polymers were characterized by...

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
Mizuki Kitamatsu ◽  
Tomoko Kashiwagi ◽  
Rino Matsuzaki ◽  
Masahiko Sisido

SPE Journal ◽  
2021 ◽  
pp. 1-18
Author(s):  
Randy Agra Pratama ◽  
Tayfun Babadagli

Summary A newly formulated chemical additive from a group of amines has been tested and applied to in-situheavy oil thermal recovery. Switchable-hydrophilicity chemical additives were successfully synthesized from N,N-dimethylcyclohexylamine in the form of homogeneous and hydrophilic solution. Fundamentally, tertiary amines comprise functional groups of hydrophilic and hydrophobic components. These unique features enable this chemical additive to wet both water and heavy oil, yielding potential interfacial tension (IFT) improvement. Furthermore, the reversible chemical reaction of this chemical additive yields both positive and negative ions. An ion pair formed due to the adsorption of cations—[C8H17NH+]—on the surface of heavy oil, whereas the anions—[HCO3−]—promoted solid-phase surface charge modification, therefore, resulting in the repulsive forces between heavy oil and the rock surface—substantially improving water-wetness and restoring an irreversible wettability alteration due to the phase change phenomenon during steam injection. In this research, two types of heavy oil acquired from a field in western Alberta encompassing the viscosity of 5,616  and 46,140 cp at 25°C was utilized in each experiment. All experiments were performed and measured at high-pressure, high-temperature (HPHT) steam conditions up to 200 psi and 200°C. We perceived that favorable IFT reduction was achieved, and irreversible wettability could be restored after combining switchable-hydrophilicity tertiary amines (SHTA) with steam as a result of the solid-phase surface charge modification to be more negatively charged. Phase distribution/residual oil in the porous media developed after steam injection was able to be favorably recovered, indicating that capillary forces could be reduced. Consequently, more than 80% of the residual oil could be recuperated post-SHTA injection, presenting favorable oil recovery performance. In addition to this promising evidence, SHTA could be potentially recovered by switching its reversible chemical reaction to be in hydrophobic form, hence, promoting this chemical additive to be both reusable and more economically effective. Comprehensive studies and analyses on interfacial properties, phase distribution in porous media, and recovery performance exhibit essential points of view in further evaluating the potential of SHTA for tertiary recovery improvement. Valuable substantiations and findings provided by our research present useful information and recommendations for fields with steam injection applications.


Peptides 1992 ◽  
1993 ◽  
pp. 334-335 ◽  
Author(s):  
Elizabeth A. Ottinger ◽  
Nuria A. Solé ◽  
Zhenping Tian ◽  
David A. Bernlohr ◽  
George Barany

1995 ◽  
Vol 73 (11) ◽  
pp. 1841-1848 ◽  
Author(s):  
Kazuyuki Sugita ◽  
Tomohito Ishida ◽  
Masahito Kushida ◽  
Kieko Harada ◽  
Kyoichi Saito ◽  
...  

Phenyl isopropenyl ketone (PIPK) copolymer films were irradiated with a low-pressure mercury lamp, and benzoyl side-chain cleavage and main-chain scission at various temperatures were followed by UV spectral changes and gel permeation chromatography, respectively. Quantum yields of both reactions and the ratio of the latter to the former reaction increased markedly above their glass transition temperatures. The main-chain scission continued to proceed by irradiation even after the side chain ceased to split. These experimental results suggest a new reaction mechanism of photosplitting of the methyl methacrylate ester side chain on the carbon adjacent to the C=C bond followed by β-scission, in addition to the known benzoyl side-chain cleavage followed by β-scission or C=C bond formation. The enhanced quantum yield for the main-chain scission of the PIPK copolymer at 130 °C realized sensitivity of 100 mJ/cm2 as a DUV resist, which was 1200 times as high as that of poly(methyl methacrylate) exposed at room temperature and developed under similar conditions. Keywords: Norrish type I cleavage, β-scission of main chain, temperature dependence, photosplitting of ester side chain, conjugated polymer radical.


Molbank ◽  
10.3390/m1119 ◽  
2020 ◽  
Vol 2020 (1) ◽  
pp. M1119 ◽  
Author(s):  
Andrei Solodinin ◽  
James Helmkay ◽  
Samuel Ollivier ◽  
Hongbin Yan

3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2′-deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2′-deoxyguanosine and C8:5′-O-cyclo-2′-deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis.


2000 ◽  
Vol 2 (5) ◽  
pp. 508-512 ◽  
Author(s):  
M. John Plater ◽  
Alison M. Murdoch ◽  
J. Richard Morphy ◽  
Zoran Rankovic ◽  
David C. Rees

1998 ◽  
Vol 9 (3) ◽  
pp. 225-231 ◽  
Author(s):  
Player ◽  
RK Maitra ◽  
RH Silverman ◽  
PF Torrence

In an attempt to develop a lead for the application of 2–5A-antisense to the targeted destruction of human immunodeficiency virus (HIV) RNA, specific target sequences within the HIV mRNAs were identified by analysis of the theoretical secondary structure. 2-5A-antisense chimeras were chosen against a total of 11 different sequences: three in the gag mRNA, three in the rev mRNA and five in the tat mRNA. 2-5A-antisense chimera synthesis was accomplished using solid-phase phosphoramidite chemistry. These chimeras were evaluated for their activity in a cell-free assay system using purified recombinant human RNase L to effect cleavage of 32P-labelled RNA transcripts of plasmids derived from HIV NL4-3. This screening revealed that of the three 2-5A-antisense chimeras targeted against gag mRNA, only one had significant HIV RNA cleavage activity, approximately10-fold-reduced compared to the parent 2-5A tetramer and comparable to that reported for the prototypical 2-5A-anti-PKR chimera, targeted against PKR mRNA. The cleavage activity of this chimera was specific, since a scrambled antisense domain chimera and a chimera without the key 5′-monophosphate moiety were both inactive. The 10 other 2-5A-antisense chimeras against tat and rev had significantly less activity. These results imply that HIV gag RNA, like PKR RNA and a model HIV tat-oligoA- vif RNA, can be cleaved using the 2-5A-antisense approach. The results further imply that not all regions of a potential RNA target are accessible to the 2-5A-antisense approach.


2021 ◽  
Author(s):  
Phil Baran ◽  
Kyle W. Knouse ◽  
Yazhong Huang ◽  
Shenjie Qiu ◽  
wei hao ◽  
...  

<div><div><div><p>The early promise of gene-based therapies is currently being realized at an accelerated pace with over 155 active clinical trials for antisense compounds and multiple FDA-approved oligonucleotide therapeutics. Fundamental advances in this area are vital and present an unprecedented opportunity to both address disease states that have been resistant to other common modalities and improve the significant sustainability challenges associated with production of these complex molecules on a commercial scale. The advent of phosphoramidite coupling chemistry and solid-phase synthesis 40 years ago democratized oligonucleotide synthesis to the scientific community, paving the way for many of these stunning developments. The reliability and generality of this approach for the preparation of native phosphate-diesters is attributed to the high reactivity of phosphorus when in the P(III)-oxidation state versus the desired P(V), as it enables rapid P-heteroatom bond formation. However, the growing demand for more diverse phosphorus-based linkages has challenged the limits of this technology. For example, the phosphorothioate (PS) linkage, which stabilizes oligonucleotides towards nuclease cleavage, is universally employed in current oligonucleotide therapeutics but is generally incorporated in racemic form. Stereodefined PS oligonucleotides may have desirable biological and physical properties but are accessed with difficulty using phosphoramidite chemistry. Here we report a flexible and efficient [P(V)]-based platform that can install a wide variety of phosphate linkages at will into oligonucleotides. This approach uses readily accessible reagents and can efficiently install not only stereodefined or racemic thiophosphates, but can install any combination of (S, R or rac)-PS with native phosphodiester (PO2) and phosphorodithioate (PS2) linkages into DNA and other modified nucleotides. Importantly this platform easily accesses this diversity under a standardized coupling protocol with sustainably prepared, stable, P(V) reagents.</p></div></div></div>


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