A new 1, 5-disubstituted Triazole DNA backbone mimic with enhanced polymerase compatibility
A new 1, 5-disubstituted Triazole DNA backbone mimic with enhanced polymerase compatibility
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 (TL2) dinucleoside phosphoramidite as well as its incorporation into oligonucleotides and compare its DNA polymerase replication competency with other TL analogues. We demonstrate that TL2 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.
16293–16301
Epple, Sven
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Modi, Aman
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Baker, Ysobel
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Wȩgrzyn, Ewa
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Traoré, Diallo
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Wanat, Przemyslaw
3729f989-a451-43a1-99d5-1cdfeb432d78
Tyburn, Agnes E. S.
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Shivalingam, Arun
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Taemaitree, Lapatrada
c069b3ef-6d34-4a85-a351-2576fb01af64
El-Sagheer, Afaf
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Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89
21 September 2021
Epple, Sven
0a1f70bd-7366-48a9-a1ee-7d747ff652ab
Modi, Aman
609fca78-9d75-4065-94d7-66914ece444f
Baker, Ysobel
4fceec1f-89ed-4a32-a753-8967daf6763a
Wȩgrzyn, Ewa
66ebfcdf-8647-4f51-86aa-6621f0b56ddb
Traoré, Diallo
4aa9dc51-758d-4a68-b9a9-9937d6505cc0
Wanat, Przemyslaw
3729f989-a451-43a1-99d5-1cdfeb432d78
Tyburn, Agnes E. S.
b591231e-c8d1-4883-a20a-7b91da89caed
Shivalingam, Arun
d6d1d27c-e4a6-4f67-b586-a34be97a1058
Taemaitree, Lapatrada
c069b3ef-6d34-4a85-a351-2576fb01af64
El-Sagheer, Afaf
05b8295a-64ad-4fdf-ad57-c34934a46c04
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89
Epple, Sven, Modi, Aman, Baker, Ysobel and Brown, Tom
,
et al.
(2021)
A new 1, 5-disubstituted Triazole DNA backbone mimic with enhanced polymerase compatibility.
Journal of the American Chemical Society, 143 (39), .
(doi:10.1021/jacs.1c08057).
Abstract
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 (TL2) dinucleoside phosphoramidite as well as its incorporation into oligonucleotides and compare its DNA polymerase replication competency with other TL analogues. We demonstrate that TL2 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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e-pub ahead of print date: 2 August 2021
Published date: 21 September 2021
Identifiers
Local EPrints ID: 475525
URI: http://eprints.soton.ac.uk/id/eprint/475525
ISSN: 0002-7863
PURE UUID: 0c61ceba-1d52-4f35-8c4a-7dec122823db
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Date deposited: 21 Mar 2023 17:35
Last modified: 28 Aug 2024 02:12
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Contributors
Author:
Sven Epple
Author:
Aman Modi
Author:
Ysobel Baker
Author:
Ewa Wȩgrzyn
Author:
Diallo Traoré
Author:
Przemyslaw Wanat
Author:
Agnes E. S. Tyburn
Author:
Arun Shivalingam
Author:
Lapatrada Taemaitree
Author:
Afaf El-Sagheer
Corporate Author: et al.
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