Dataset Information

A Study on Synthesis and Upscaling of 2'-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis.

ABSTRACT: 2'-O-(N-(Aminoethyl)carbamoyl)methyl-modified 5-methyluridine (AECM-MeU) and 5-methylcytidine (AECM-MeC) phosphoramidites are reported for the first time and prepared in multigram quantities. The syntheses of AECM-MeU and AECM-MeC nucleosides are designed for larger scales (approx. 20 g up until phosphoramidite preparation steps) using low-cost reagents and minimizing chromatographic purifications. Several steps were screened for best conditions, focusing on the most crucial steps such as N3 and/or 2'-OH alkylations, which were improved for larger scale synthesis using phase transfer catalysis (PTC). Moreover, the need of chromatographic purifications was substantially reduced by employing one-pot synthesis and improved work-up strategies.

SUBMITTER: Karale K

PROVIDER: S-EPMC8619030 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Publications

A Study on Synthesis and Upscaling of 2'-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis.

Karalė Kristina K Bollmark Martin M Stulz Rouven R Honcharenko Dmytro D Tedebark Ulf U Strömberg Roger R

Molecules (Basel, Switzerland) 20211117 22

2'-O-(N-(Aminoethyl)carbamoyl)methyl-modified 5-methyluridine (AECM-MeU) and 5-methylcytidine (AECM-MeC) phosphoramidites are reported for the first time and prepared in multigram quantities. The syntheses of AECM-MeU and AECM-MeC nucleosides are designed for larger scales (approx. 20 g up until phosphoramidite preparation steps) using low-cost reagents and minimizing chromatographic purifications. Several steps were screened for best conditions, focusing on the most crucial steps ...[more]

PMID: 34834019

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Project description:Research on two-dimensional materials is one of the most relevant fields in materials science. Layered double hydroxides (LDHs), a versatile class of anionic clays, exhibit great potential in photocatalysis, energy storage and conversion, and environmental applications. However, its implementation in real-life devices requires the development of efficient and reproducible large-scale synthesis processes. Unfortunately, reliable methods that allow for the production of large quantities of two-dimensional LDHs with well-defined morphologies and high crystallinity are very scarce. In this work, we carry out a scale-up of the urea-based CoAl-LDH synthesis method. We thoroughly study the effects of the mass scale-up (25-fold: up to 375 mM) and the volumetric scale-up (20-fold: up to 2 L). For this, we use a combination of several structural (XRD, TGA, and N2 and CO2 isotherms), microscopic (SEM, TEM, and AFM), magnetic (SQUID), and spectroscopic techniques (ATR-FTIR, UV-vis, XPS, ICP-MS, and XANES-EXAFS). In the case of the volumetric scale-up, a reduction of 45% in the lateral dimensions of the crystals (from 3.7 to 2.0 µm) is observed as the reaction volume increases. This fact is related to modified heating processes affecting the alkalinization rates and, concomitantly, the precipitation, even under recrystallization at high temperatures. In contrast, for the tenfold mass scale-up, similar morphological features were observed and assigned to changes in nucleation and growth. However, at higher concentrations, simonkolleite-like Co-based layered hydroxide impurities are formed, indicating a phase competition during the precipitation related to the thermodynamic stability of the growing phases. Overall, this work demonstrates that it is possible to upscale the synthesis of high-quality hexagonal CoAl-LDH in a reproducible manner. It highlights the most critical synthesis aspects that must be controlled and provides various fingerprints to trace the quality of these materials. These results will contribute to bringing the use of these 2D layered materials closer to reality in different applications of interest.

Dataset Information

A Study on Synthesis and Upscaling of 2'-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis.

Publications

A Study on Synthesis and Upscaling of 2'-<i>O</i>-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis.

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