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mRNA Cap Modification through Carbamate Chemistry: Synthesis of Amino‐ and Carboxy‐Functionalised Cap Analogues Suitable for Labelling and Bioconjugation (Eur. J. Org. Chem. 28/2015)
Author(s) -
Warminski Marcin,
Warminska Zofia,
Kowalska Joanna,
Jemielity Jacek
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201590079
Subject(s) - chemistry , bioconjugation , linker , translation (biology) , messenger rna , nucleotide , rna , amino acid , labelling , chemical biology , eif4e , biochemistry , stereochemistry , chemical modification , protein biosynthesis , gene , computer science , operating system
The cover picture shows a variety of 5′ mRNA cap analogues containing linkers terminated with amino or carboxy groups and their possible applications in studies on mRNA metabolism. One‐pot synthesis of 25′‐O/35′‐O‐carbamoyl nucleotides using carbonyldiimidazole chemistry was optimized and applied to synthesize 15 functionalized cap analogues. The analogues can be divided into five groups, represented by subway lines of different colors, based on the position of linker attachment and triphosphate modification site. Each group is connected to different possible applications, such as investigation of mRNA translation, degradation and localization as well as construction of affinity resins for cap‐binding proteins. The choice of modification sites was dictated by our knowledge of cap recognition by various proteins: eukaryotic translation initiation factor 4E (eIF4E), Decapping Scavenger (DcpS), decapping complex Dcp2/Dcp1 and RNA polymerases enabling incorporation of functionalized cap analogues into the 55′ end of transcripts. Details of this work are discussed in the article by J. Kowalska, J. Jemielity et al. on 5949 ff .