ArticleJournal of the American Chemical Society2013
Probing the mechanism of cyanobacterial aldehyde decarbonylase using a cyclopropyl aldehyde.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 65 citations in OpenAlex.
- Incorporation, fate, and turnover of free fatty acids in cyanobacteria.FEMS microbiology reviews · 2023Review
- Utilizing Alcohol for Alkane Biosynthesis by Introducing a Fatty Alcohol Dehydrogenase.Applied and environmental microbiology · 2022Article
- Recent advances in the improvement of cyanobacterial enzymes for bioalkane production.Microbial cell factories · 2022Review
- Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Fingerprinting cities: differentiating subway microbiome functionality.Biology direct · 2019Article
- Addition of formate dehydrogenase increases the production of renewable alkane from an engineered metabolic pathway.The Journal of biological chemistry · 2019Article
- A consensus-guided approach yields a heat-stable alkane-producing enzyme and identifies residues promoting thermostability.The Journal of biological chemistry · 2018Article
- Comparison of orthologous cyanobacterial aldehyde deformylating oxygenases in the production of volatile C3-C7 alkanes in engineeredMetabolic engineering communications · 2017Article
- Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.Journal of the American Chemical Society · 2017Article
- Convergent synthesis of a deuterium-labeled serine dipeptide lipid for analysis of biological samples.Journal of labelled compounds & radiopharmaceuticals · 2017Article
- Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Review
- Identification of residues important for the activity of aldehyde-deformylating oxygenase through investigation into the structure-activity relationship.BMC biotechnology · 2017Article
- Whole-cell biocatalytic and de novo production of alkanes from free fatty acids in Saccharomyces cerevisiae.Biotechnology and bioengineering · 2017Article
- Microbial alkane production for jet fuel industry: motivation, state of the art and perspectives.Microbial biotechnology · 2017Review
- Structure-oriented substrate specificity engineering of aldehyde-deformylating oxygenase towards aldehydes carbon chain length.Biotechnology for biofuels · 2016Article
- Conversion of Aldehyde to Alkane by a Peroxoiron(III) Complex: A Functional Model for the Cyanobacterial Aldehyde-Deformylating Oxygenase.Journal of the American Chemical Society · 2015Article
- Mechanism of action of thalassospiramides, a new class of calpain inhibitors.Scientific reports · 2015Article
- An unusual peroxo intermediate of the arylamine oxygenase of the chloramphenicol biosynthetic pathway.Journal of the American Chemical Society · 2015Article
- Structural insights into the catalytic mechanism of aldehyde-deformylating oxygenases.Protein & cell · 2015Article
- Insights into substrate and metal binding from the crystal structure of cyanobacterial aldehyde deformylating oxygenase with substrate bound.ACS chemical biology · 2014Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Cyanobacterial aldehyde decarbonylase (cAD) is a non-heme diiron oxygenase that catalyzes the conversion of fatty aldehydes to alkanes and formate. The mechanism of this chemically unusual reaction is poorly understood. We have investigated the mechanism of C1-C2 bond cleavage by cAD using a fatty aldehyde that incorporates a cyclopropyl group, which can act as a radical clock. When reacted with cAD, the cyclopropyl aldehyde produces 1-octadecene as the rearranged product, providing evidence for a radical mechanism for C-C bond scission. In an alternate pathway, the cyclopropyl aldehyde acts as a mechanism-based irreversible inhibitor of cAD through covalent binding of the alkyl chain to the enzyme.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.