Issue 28, 2024, Issue in Progress

Improved synthesis and polymerase recognition of 7-deaza-7-modified α-l-threofuranosyl guanosine analogs

Abstract

Threofuranosyl nucleic acid (TNA), an artificial genetic polymer known for its nuclease resistance and acid stability, has grown in popularity as a genetically-encoded material for applications in synthetic biology and biomedicine. TNA oligonucleotide synthesis requires enzymatic or solid phase synthesis pathways that rely on monomer building blocks that are not commercially available and can only be obtained by chemical synthesis. Here we present a synthetic route to 7-deaza-7-modified tGTP and phosphoramidite analogs that is operationally simpler than our previously described strategy. The new methodology offers an HPLC-free route to tGTP analogs that are recognized by engineered TNA polymerases and can be incorporated with continued TNA synthesis.

Graphical abstract: Improved synthesis and polymerase recognition of 7-deaza-7-modified α-l-threofuranosyl guanosine analogs

Supplementary files

Article information

Article type
Paper
Submitted
23 Apr 2024
Accepted
05 Jun 2024
First published
19 Jun 2024
This article is Open Access
Creative Commons BY license

RSC Adv., 2024,14, 19701-19706

Improved synthesis and polymerase recognition of 7-deaza-7-modified α-L-threofuranosyl guanosine analogs

B. Barpuzary, S. Negria and J. C. Chaput, RSC Adv., 2024, 14, 19701 DOI: 10.1039/D4RA03029J

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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