ArticleArchives of biochemistry and biophysics2018
Decarbamoylation of acetylcholinesterases is markedly slowed as carbamoyl groups increase in size.
Article in Archives of biochemistry and biophysics, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 18 citations in OpenAlex.
- Current-use and legacy pesticides in canal waters of Chiang Mai, Thailand, during longan flowering and fruit set: occurrence and ecological and human health risk assessment.Scientific reports · 2026Article
- A cocaine hydrolase engineered from human butyrylcholinesterase as a medical countermeasure for aldicarb poisoning.Chemico-biological interactions · 2025Article
- Treatment of acute organophosphate poisoning by using a cocaine hydrolase engineered from human butyrylcholinesterase.Chemico-biological interactions · 2025Article
- Bioactive structures for inhibitors ofFuture medicinal chemistry · 2025Article
- Facile Synthesis of Carbamoyl FluoridesACS omega · 2025Article
- Rivastigmine-Bambuterol Hybrids as Selective Butyrylcholinesterase Inhibitors.Molecules (Basel, Switzerland) · 2023Article
- Profiling the Tox21 Chemical Collection for Acetylcholinesterase Inhibition.Environmental health perspectives · 2021Article
- Solvent Deuterium Oxide Isotope Effects on the Reactions of Organophosphorylated Acetylcholinesterase.Molecules (Basel, Switzerland) · 2020Article
- Rate-limiting step in the decarbamoylation of acetylcholinesterases with large carbamoyl groups.Chemico-biological interactions · 2019Review
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
Carbamates are esters of substituted carbamic acids that react with acetylcholinesterase (AChE) by initially transferring the carbamoyl group to a serine residue in the enzyme active site accompanied by loss of the carbamate leaving group followed by hydrolysis of the carbamoyl enzyme. This hydrolysis, or decarbamoylation, is relatively slow, and half-lives of carbamoylated AChEs range from 4 min to more than 30 days. Therefore, carbamates are effective AChE inhibitors that have been developed as insecticides and as therapeutic agents. We show here, in contrast to a previous report, that decarbamoylation rate constants are independent of the leaving group for a series of carbamates with the same carbamoyl group. When the alkyl substituents on the carbamoyl group increased in size from N-monomethyl- to N,N-dimethyl-, N-ethyl-N-methyl-, or N,N-diethyl-, the decarbamoylation rate constants decreased by 4-, 70-, and 800-fold, respectively. We suggest that this relationship arises as a result of active site distortion, particularly in the acyl pocket of the active site. Furthermore, solvent deuterium oxide isotope effects for decarbamoylation decreased from 2.8 for N-monomethylcarbamoyl AChE to 1.1 for N,N-diethylcarbamoyl AChE, indicating a shift in the rate-limiting step from general acid-base catalysis to a likely conformational change in the distorted active site.
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