TCI Chemistry News
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October 2023
TCI offers an extensive catalog of over 30,000 high quality organic reagents suitable for benchtop-to-bulk chemistry. This issue covers our chemistry topics as follows:
- Base-modified Ribonucleoside Triphosphates for mRNA Drug Discovery
- DMAPO as Oxidant and Condensing Agent
- Bromination of an Alkyl Alcohol through the Appel Reaction
- Methyl Esterification of Carboxylic Acid Using TMS-Diazomethane
Base-modified Ribonucleoside Triphosphates for mRNA Drug Discovery
RNA base-modified ribonucleoside triphosphate is used in in vitro transcription (IVT) of RNA medicines. RNA vaccines work by inducing the body to express viral proteins, which in turn stimulate the immune system to produce antibodies. In this process, the mRNA's own evasion of the immune system is important, along with the mRNA's translational efficiency. It is known that swapping nucleotides for a related analogue helped to make the mRNA less conspicuous to the immune system.TCI has commercialized N1-methyl pseudouridine 5'-triphosphate sodium salt [M3544], pseudouridine 5'-triphosphate sodium salt [P3045], 5-methyluridine 5'-triphosphate sodium salt [M3582], 5-methylcytidine 5'-triphosphate sodium salt [M3583], 5-methoxyuridine 5'-triphosphate sodium salt [M3584] which are expected to have high translational efficiency and immunogenicity reduction effects, as raw materials for the synthesis of modified RNA medicines. These products have been checked for DNase and RNase contamination and functionality in IVT.
In recent years, studies in this field have been very active, new effects of base-modified nucleotides are continuously being reported. TCI is capable of performing the full process from modification of bases to triphosphorylation in-house, and can also provide base-modified triphosphates that are not listed in our catalog. TCI are also available for consultation on scale-up manufacturing.
DMAPO as Oxidant and Condensing Agent
4-(Dimethylamino)pyridine N-oxide (= DMAPO) [D3220] is utilized as an oxidant and condensing agent. For example, Yamaguchi et al. reported the efficient conversion of alkyl halides to carbonyl groups by using DMAPO as an oxidant. In this reaction, primary and secondary alkyl halides are used as substrates and can be oxidized to aldehydes and ketones, respectively. On the other hand, there are reports including improved yields of lactonization by using DMAPO as a condensing agent instead of DMAP and amidation in combination with arylboronic acids, which is applicable to less reactive carboxylic acids. Furthermore, Sasaki et al. recently reported an amidation reaction using Boc2O and a catalytic amount of DMAPO. This reaction proceeds under mild conditions in one-pot and is applicable to less reactive amines such as indole and carbazole, so that it is expected to be used in drug discovery research.
TCI Practical Example: Bromination of an Alkyl Alcohol through the Appel Reaction
TCI introduces the bromination reaction of the hydroxy group of 2-phenethyl alcohol using carbon tetrabromide [T0038] and triphenylphosphine [T0519]. (2-Bromoethyl)benzene has been obtained at 96% yield.
TCI Practical Example: Methyl Esterification of Carboxylic Acid Using TMS-Diazomethane
We are proud to present the methyl esterification of the protected serine using TMS-diazomethane [T1146] as an esterification agent. TMS-diazomethane is safer and easier to handle than diazomethane.
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