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Title: Photosynthetic production of the nitrogen-rich compound guanidine

Abstract

The development of an sustainable economy calls for improved energy utilization and storage technologies. Although battery- and carbon-based routes have gained tremendous attention, nitrogen-based routes have rarely been exploited so far. Guanidine (CH5N3) which contains 71.1% nitrogen by mass is an exemplary chemical to explore the nitrogen-based routes of energy utilization and storage. Guanidine has a variety of applications including its use as a slow-release fertilizer, a propellant, or as a precursor to pharmaceuticals and antimicrobial polymers. The conventional chemical synthesis of guanidine through the Frank–Caro process is energy-intensive, consumes fossil fuels, and is detrimental to the environment. Herein, a de novo guanidine biosynthesis (GUB) cycle is proposed with CO2 and nitrate/ammonium as the carbon and nitrogen sources, respectively. The ATP and NAD(P)H needed to drive the GUB cycle are generated via photosynthesis in an engineered cyanobacterium Synechocystis sp. PCC 6803 expressing an ethylene-forming enzyme (EFE). Up to 586.5 mg L-1 (9.9 mM) guanidine was produced after seven days of photoautotrophic cultivation, with an average productivity of 83.8 mg L-1 day-1. In addition, guanidine was directly biosynthesized from CO2, N2 and H2O in an engineered N2-fixing cyanobacterium Anabaena sp. PCC 7120 expressing the EFE. This work demonstrates the first biologicalmore » conversion of renewable solar energy into chemical energy stored in the nitrogen-rich compound guanidine, which could shed light on harnessing the biological nitrogen metabolism for energy utilization and storage.« less

Authors:
ORCiD logo [1]; ORCiD logo [1];  [2];  [2];  [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Biosciences Center, National Renewable Energy Laboratory, Golden, USA
  2. Department of Biology & Microbiology, South Dakota State University, Brookings, USA
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1528658
Alternate Identifier(s):
OSTI ID: 1513042; OSTI ID: 1515762
Report Number(s):
NREL/JA-2700-73223
Journal ID: ISSN 1463-9262; GRCHFJ
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Journal Article: Published Article
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Name: Green Chemistry Journal Volume: 21 Journal Issue: 11; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; guanidine; cyanobacterium; nitrogen fixation; synechocystis; Anabaena

Citation Formats

Wang, Bo, Dong, Tao, Myrlie, Aldon, Gu, Liping, Zhu, Huilan, Xiong, Wei, Maness, PinChing, Zhou, Ruanbao, and Yu, Jianping. Photosynthetic production of the nitrogen-rich compound guanidine. United Kingdom: N. p., 2019. Web. doi:10.1039/C9GC01003C.
Wang, Bo, Dong, Tao, Myrlie, Aldon, Gu, Liping, Zhu, Huilan, Xiong, Wei, Maness, PinChing, Zhou, Ruanbao, & Yu, Jianping. Photosynthetic production of the nitrogen-rich compound guanidine. United Kingdom. https://doi.org/10.1039/C9GC01003C
Wang, Bo, Dong, Tao, Myrlie, Aldon, Gu, Liping, Zhu, Huilan, Xiong, Wei, Maness, PinChing, Zhou, Ruanbao, and Yu, Jianping. 2019. "Photosynthetic production of the nitrogen-rich compound guanidine". United Kingdom. https://doi.org/10.1039/C9GC01003C.
@article{osti_1528658,
title = {Photosynthetic production of the nitrogen-rich compound guanidine},
author = {Wang, Bo and Dong, Tao and Myrlie, Aldon and Gu, Liping and Zhu, Huilan and Xiong, Wei and Maness, PinChing and Zhou, Ruanbao and Yu, Jianping},
abstractNote = {The development of an sustainable economy calls for improved energy utilization and storage technologies. Although battery- and carbon-based routes have gained tremendous attention, nitrogen-based routes have rarely been exploited so far. Guanidine (CH5N3) which contains 71.1% nitrogen by mass is an exemplary chemical to explore the nitrogen-based routes of energy utilization and storage. Guanidine has a variety of applications including its use as a slow-release fertilizer, a propellant, or as a precursor to pharmaceuticals and antimicrobial polymers. The conventional chemical synthesis of guanidine through the Frank–Caro process is energy-intensive, consumes fossil fuels, and is detrimental to the environment. Herein, a de novo guanidine biosynthesis (GUB) cycle is proposed with CO2 and nitrate/ammonium as the carbon and nitrogen sources, respectively. The ATP and NAD(P)H needed to drive the GUB cycle are generated via photosynthesis in an engineered cyanobacterium Synechocystis sp. PCC 6803 expressing an ethylene-forming enzyme (EFE). Up to 586.5 mg L-1 (9.9 mM) guanidine was produced after seven days of photoautotrophic cultivation, with an average productivity of 83.8 mg L-1 day-1. In addition, guanidine was directly biosynthesized from CO2, N2 and H2O in an engineered N2-fixing cyanobacterium Anabaena sp. PCC 7120 expressing the EFE. This work demonstrates the first biological conversion of renewable solar energy into chemical energy stored in the nitrogen-rich compound guanidine, which could shed light on harnessing the biological nitrogen metabolism for energy utilization and storage.},
doi = {10.1039/C9GC01003C},
url = {https://www.osti.gov/biblio/1528658}, journal = {Green Chemistry},
issn = {1463-9262},
number = 11,
volume = 21,
place = {United Kingdom},
year = {Tue Jun 04 00:00:00 EDT 2019},
month = {Tue Jun 04 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at https://doi.org/10.1039/C9GC01003C

Citation Metrics:
Cited by: 12 works
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Works referenced in this record:

Metabolism of Free Guanidine in Bacteria Is Regulated by a Widespread Riboswitch Class
journal, January 2017


Ammonia Triggers Photodamage of Photosystem II in the Cyanobacterium Synechocystis sp. Strain PCC 6803
journal, March 2008


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The cyanobacterial ornithine–ammonia cycle involves an arginine dihydrolase
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Ethylene Synthesis and Regulated Expression of Recombinant Protein in Synechocystis sp. PCC 6803
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journal, January 2017


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A Genetic Toolbox for Modulating the Expression of Heterologous Genes in the Cyanobacterium Synechocystis sp. PCC 6803
journal, August 2017


Engineering cyanobacteria for photosynthetic production of 3-hydroxybutyrate directly from CO2
journal, March 2013


Ammonium assimilation in cyanobacteria
journal, February 2005


The plasticity of cyanobacterial metabolism supports direct CO2 conversion to ethylene
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Sustained photosynthetic conversion of CO2 to ethylene in recombinant cyanobacterium Synechocystis 6803
journal, January 2012


Ethylene production with engineered Synechocystis sp PCC 6803 strains
journal, February 2017


Unlocking the photobiological conversion of CO 2 to ( R )-3-hydroxybutyrate in cyanobacteria
journal, January 2018


The chemistry and biology of guanidine natural products
journal, January 2017


Structural and stereoelectronic insights into oxygenase-catalyzed formation of ethylene from 2-oxoglutarate
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Photosynthetic nitrate assimilation in cyanobacteria
journal, February 2005


Metabolic engineering of microorganisms for the production of L-arginine and its derivatives
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Engineering cyanobacteria for the production of a cyclic hydrocarbon fuel from CO 2 and H 2 O
journal, January 2014


Promising silicones modified with cationic biocides for the development of antimicrobial medical devices
journal, June 2017


Ammonia and hydrogen production by immobilized cyanobacteria
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Guanidine sulphate: Slow release of mineral nitrogen during incubation in soil
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Structures and Mechanisms of the Non-Heme Fe(II)- and 2-Oxoglutarate-Dependent Ethylene-Forming Enzyme: Substrate Binding Creates a Twist
journal, August 2017


Ethylene-forming enzyme and bioethylene production
journal, January 2014


The Biology of Free Guanidine As Revealed by Riboswitches
journal, January 2017


Works referencing / citing this record:

Monomer sequence design at two solvent interface enables the synthesis of highly photoactive carbon nitride
journal, January 2019


Increased ethylene production by overexpressing phosphoenolpyruvate carboxylase in the cyanobacterium Synechocystis PCC 6803
journal, January 2020