A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions

Hidenori Okamura; Sidney Becker; Niklas Tiede; Stefan Wiedemann; Jonas Feldmann; Thomas Carell

doi:10.1039/C8CC09435G

A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions

Hidenori Okamura, Sidney Becker, Niklas Tiede, Stefan Wiedemann, Jonas Feldmann, Thomas Carell

Division of Organic- and Biomaterials Research

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

10 Citations (Scopus)

Abstract

Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.

Original language	English
Pages (from-to)	1939-1942
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	13
DOIs	https://doi.org/10.1039/C8CC09435G
Publication status	Published - 2019

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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title = "A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions",

abstract = "Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.",

author = "Hidenori Okamura and Sidney Becker and Niklas Tiede and Stefan Wiedemann and Jonas Feldmann and Thomas Carell",

note = "Funding Information: This study was supported by the Deutsche Forschungsge-meinschaft (DFG) for financial support via the programs SFB1032 (TP-A5), SFB749 (TP-A4), SPP-1784, CA275/11-1. Additional funding from the Excellence Cluster EXC117 CiPSM is acknowledged. This project has received funding from the European Research Council (ERC) under the European Union{\textquoteright}s Horizon 2020 research and innovation programme (Project ID: 741912). H. O. received a Marie Sklodowska-Curie Individual Fellowship (Project ID: 752420) from the European Commission.",

year = "2019",

doi = "10.1039/C8CC09435G",

language = "English",

volume = "55",

pages = "1939--1942",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions

AU - Okamura, Hidenori

AU - Becker, Sidney

AU - Tiede, Niklas

AU - Wiedemann, Stefan

AU - Feldmann, Jonas

AU - Carell, Thomas

N1 - Funding Information: This study was supported by the Deutsche Forschungsge-meinschaft (DFG) for financial support via the programs SFB1032 (TP-A5), SFB749 (TP-A4), SPP-1784, CA275/11-1. Additional funding from the Excellence Cluster EXC117 CiPSM is acknowledged. This project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (Project ID: 741912). H. O. received a Marie Sklodowska-Curie Individual Fellowship (Project ID: 752420) from the European Commission.

PY - 2019

Y1 - 2019

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AB - Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.

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