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Issue 69, 2019
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Novel entry to the synthesis of (S)- and (R)-5-methoxycarbonylhydroxymethyluridines – a diastereomeric pair of wobble tRNA nucleosides

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Abstract

Two novel methods for the preparation of the virtually equimolar mixtures of (S)- and (R)-diastereomers of 5-methoxycarbonylhydroxymethyluridine (mchm5U) have been developed. The first method involved α-hydroxylation of a 5-malonate ester derivative of uridine (5) with SeO2, followed by transformation to (S)- and (R)-5-carboxymethyluridines (cm5U, 8) and, finally, into the corresponding methyl esters. In the second approach, (S)- and (R)-mchm5-uridines were obtained starting from 5-formyluridine derivative (9) by hydrolysis of the imidate salt (11) prepared in the acid catalyzed reaction of 5-cyanohydrin-containing uridine (10b) with methyl alcohol. In both methods, the (S)- and (R) diastereomers of mchm5U were effectively separated by preparative C18 RP HPLC.

Graphical abstract: Novel entry to the synthesis of (S)- and (R)-5-methoxycarbonylhydroxymethyluridines – a diastereomeric pair of wobble tRNA nucleosides

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Article information


Submitted
18 Oct 2019
Accepted
28 Nov 2019
First published
06 Dec 2019

This article is Open Access

RSC Adv., 2019,9, 40507-40512
Article type
Paper

Novel entry to the synthesis of (S)- and (R)-5-methoxycarbonylhydroxymethyluridines – a diastereomeric pair of wobble tRNA nucleosides

R. Borowski, A. Dziergowska, E. Sochacka and G. Leszczynska, RSC Adv., 2019, 9, 40507 DOI: 10.1039/C9RA08548C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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