Deoxynucleoside triphosphates bearing histamine, carboxylic acid, and hydroxyl residues--synthesis and biochemical characterization.

Hollenstein, Marcel (2013). Deoxynucleoside triphosphates bearing histamine, carboxylic acid, and hydroxyl residues--synthesis and biochemical characterization. Organic & biomolecular chemistry, 11(31), pp. 5162-5172. Royal Society of Chemistry 10.1039/c3ob40842f

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Modified nucleoside triphosphates (dA(Hs)TP, dU(POH)TP, and dC(Val)TP) bearing imidazole, hydroxyl, and carboxylic acid residues connected to the purine and pyrimidine bases through alkyne linkers were prepared. These modified dN*TPs were excellent substrates for various DNA polymerases in primer extension reactions. Moreover, the combined use of terminal deoxynucleotidyl transferase (TdT) and the modified dNTPs led to efficient tailing reactions that rival those of natural counterparts. Finally, the triphosphates were tolerated by polymerases under PCR conditions, and the ensuing modified oligonucleotides served as templates for the regeneration of unmodified DNA. Thus, these modified dN*TPs are fully compatible with in vitro selection methods and can be used to develop artificial peptidases based on DNA.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Hollenstein, Marcel

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1477-0520

Publisher:

Royal Society of Chemistry

Language:

English

Submitter:

Andrea Stettler

Date Deposited:

25 Jul 2014 11:17

Last Modified:

30 Mar 2015 20:38

Publisher DOI:

10.1039/c3ob40842f

PubMed ID:

23817514

BORIS DOI:

10.7892/boris.54954

URI:

https://boris.unibe.ch/id/eprint/54954

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