Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block

Jianfeng Cai; Xiaoxu Li; John Stephen Taylor

doi:10.1021/ol0478382

Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block

Jianfeng Cai
, Xiaoxu Li
, John Stephen Taylor

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

(Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in k_cat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

Original language	English
Pages (from-to)	751-754
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	5
DOIs	https://doi.org/10.1021/ol0478382
State	Published - Mar 3 2005

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abstract = "(Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in kcat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.",

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AU - Cai, Jianfeng

AU - Li, Xiaoxu

AU - Taylor, John Stephen

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Y1 - 2005/3/3

N2 - (Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in kcat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

AB - (Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in kcat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

UR - https://www.scopus.com/pages/publications/15044343679

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DO - 10.1021/ol0478382

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Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block

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