A New 1,5-Disubstituted Triazole DNA Backbone Mimic with Enhanced Polymerase Compatibility | Zendy

Sven Epple | Zendy; Aman Modi | Zendy; Ysobel R. Baker | Zendy; Ewa Węgrzyn | Zendy; Diallo Traoré | Zendy; Przemysław Wanat | Zendy; Agnes E. S. Tyburn | Zendy; Arun Shivalingam | Zendy; Lapatrada Taemaitree | Zendy; Afaf H. ElSagheer | Zendy; Tom Brown | Zendy

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A New 1,5-Disubstituted Triazole DNA Backbone Mimic with Enhanced Polymerase Compatibility

Author(s) -

Sven Epple,

Aman Modi,

Ysobel R. Baker,

Ewa Węgrzyn,

Diallo Traoré,

Przemysław Wanat,

Agnes E. S. Tyburn,

Arun Shivalingam,

Lapatrada Taemaitree,

Afaf H. ElSagheer,

Tom Brown

Publication year - 2021

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.1c08057

Subject(s) - chemistry , triazole , compatibility (geochemistry) , polymerase , dna , combinatorial chemistry , dna polymerase , stereochemistry , biochemistry , organic chemistry , chemical engineering , engineering

Triazole linkages (TLs) are mimics of the phosphodiester bond in oligonucleotides with applications in synthetic biology and biotechnology. Here we report the RuAAC-catalyzed synthesis of a novel 1,5-disubstituted triazole (TL 2 ) dinucleoside phosphoramidite as well as its incorporation into oligonucleotides and compare its DNA polymerase replication competency with other TL analogues. We demonstrate that TL 2 has superior replication kinetics to these analogues and is accurately replicated by polymerases. Derived structure-biocompatibility relationships show that linker length and the orientation of a hydrogen bond acceptor are critical and provide further guidance for the rational design of artificial biocompatible nucleic acid backbones.

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