Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates

Enver Cagri Izgu; Seung Soo Oh; Jack W. Szostak

doi:https://doi.org/10.1039/c5cc10317g

Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates

Enver Cagri Izgu, Seung Soo Oh, Jack W. Szostak

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

6 Scopus citations

Abstract

We present a scalable synthesis of 3′-amino-3′-deoxy-2-thio-thymidine-5′-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the rate of template copying by 5-fold compared with the 3′-amino-3′-deoxy-T monomer, while the 3′-amino monomers exhibit a 2- to 30-fold enhancement compared with their ribonucleotide counterparts.

Original language	American English
Pages (from-to)	3684-3686
Number of pages	3
Journal	Chemical Communications
Volume	52
Issue number	18
DOIs	https://doi.org/10.1039/c5cc10317g
State	Published - 2016
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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https://doi.org/10.1039/c5cc10317g

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title = "Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates",

abstract = "We present a scalable synthesis of 3′-amino-3′-deoxy-2-thio-thymidine-5′-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the rate of template copying by 5-fold compared with the 3′-amino-3′-deoxy-T monomer, while the 3′-amino monomers exhibit a 2- to 30-fold enhancement compared with their ribonucleotide counterparts.",

author = "Izgu, {Enver Cagri} and Oh, {Seung Soo} and Szostak, {Jack W.}",

note = "Funding Information: We thank Dr Shao-Liang Zheng (Harvard) for help with X-ray data collection and structure determination, and Prof. Mohammad Movassaghi (MIT) and Dr Justin Kim (MIT) for their guidance in performing safe hydrogen sulfide experiments. We also thank Dr Lijun Zhou and Ms Moriana Haj for technical assistance and Dr Albert C. Fahrenbach, Dr Victor S. Lelyveld, Mr Tony Z. Jia, and Mr Chun Pong Tam for helpful discussions. J. W. S. is an Investigator of the Howard Hughes Medical Institute. This work was supported in part by a grant (290363) from the Simons Foundation to J. W. S. Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "https://doi.org/10.1039/c5cc10317g",

language = "American English",

volume = "52",

pages = "3684--3686",

journal = "Chemical Communications (London)",

issn = "0009-241X",

publisher = "Royal Society of Chemistry",

number = "18",

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TY - JOUR

T1 - Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates

AU - Izgu, Enver Cagri

AU - Oh, Seung Soo

AU - Szostak, Jack W.

N1 - Funding Information: We thank Dr Shao-Liang Zheng (Harvard) for help with X-ray data collection and structure determination, and Prof. Mohammad Movassaghi (MIT) and Dr Justin Kim (MIT) for their guidance in performing safe hydrogen sulfide experiments. We also thank Dr Lijun Zhou and Ms Moriana Haj for technical assistance and Dr Albert C. Fahrenbach, Dr Victor S. Lelyveld, Mr Tony Z. Jia, and Mr Chun Pong Tam for helpful discussions. J. W. S. is an Investigator of the Howard Hughes Medical Institute. This work was supported in part by a grant (290363) from the Simons Foundation to J. W. S. Publisher Copyright: © 2016 The Royal Society of Chemistry.

PY - 2016

Y1 - 2016

N2 - We present a scalable synthesis of 3′-amino-3′-deoxy-2-thio-thymidine-5′-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the rate of template copying by 5-fold compared with the 3′-amino-3′-deoxy-T monomer, while the 3′-amino monomers exhibit a 2- to 30-fold enhancement compared with their ribonucleotide counterparts.

AB - We present a scalable synthesis of 3′-amino-3′-deoxy-2-thio-thymidine-5′-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the rate of template copying by 5-fold compared with the 3′-amino-3′-deoxy-T monomer, while the 3′-amino monomers exhibit a 2- to 30-fold enhancement compared with their ribonucleotide counterparts.

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JF - Chemical Communications (London)

IS - 18

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Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates

Abstract

ASJC Scopus subject areas

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