S-Adenosylmethionine: more than just a methyl donor
Literature Information
Yu-Hsuan Lee, Daan Ren, Byungsun Jeon
Covering: from 2000 up to the very early part of 2023 S-Adenosyl-L-methionine (SAM) is a naturally occurring trialkyl sulfonium molecule that is typically associated with biological methyltransfer reactions. However, SAM is also known to donate methylene, aminocarboxypropyl, adenosyl and amino moieties during natural product biosynthetic reactions. The reaction scope is further expanded as SAM itself can be modified prior to the group transfer such that a SAM-derived carboxymethyl or aminopropyl moiety can also be transferred. Moreover, the sulfonium cation in SAM has itself been found to be critical for several other enzymatic transformations. Thus, while many SAM-dependent enzymes are characterized by a methyltransferase fold, not all of them are necessarily methyltransferases. Furthermore, other SAM-dependent enzymes do not possess such a structural feature suggesting diversification along different evolutionary lineages. Despite the biological versatility of SAM, it nevertheless parallels the chemistry of sulfonium compounds used in organic synthesis. The question thus becomes how enzymes catalyze distinct transformations via subtle differences in their active sites. This review summarizes recent advances in the discovery of novel SAM utilizing enzymes that rely on Lewis acid/base chemistry as opposed to radical mechanisms of catalysis. The examples are categorized based on the presence of a methyltransferase fold and the role played by SAM within the context of known sulfonium chemistry.
Related Literature
Influence of PPH dendrimers' surface functions on the activation of human monocytes: a study of their interactions with pure lipid model systems
F. Ielasi, S. Fruchon, R. Poupot, M. Blanzat
DOI: 10.1039/C6CP03536A
The crystal structure and chemical state of aluminum-doped hydroxyapatite by experimental and first principles calculation studies
Ming Wang, Liping Wang, Chao Shi, Tian Sun, Yingchun Zhu
DOI: 10.1039/C6CP03230C
Towards an accurate specific reaction parameter density functional for water dissociation on Ni(111): RPBE versus PW91
Bin Jiang, Hua Guo
DOI: 10.1039/C6CP03707K
Computational simulation and interpretation of the low-lying excited electronic states and electronic spectrum of thioanisole
Shaohong L. Li, Xuefei Xu, Donald G. Truhlar
DOI: 10.1039/C5CP02461G
Correlation of three-liquid-phase equilibria involving ionic liquids
I. Rodríguez-Escontrela, A. Arce, A. Soto, A. Marcilla, M. M. Olaya, J. A. Reyes-Labarta
DOI: 10.1039/C6CP03467E
Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study
DOI: 10.1039/C5CP01596K
Hydrogen-doping induced reduction in the phase transition temperature of VO2: a first-principles study
Yuanyuan Cui, Lanli Chen, Yanfeng Gao
DOI: 10.1039/C5CP03267A
You might also like
What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?
Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...
How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?
Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...
How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?
Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...
What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?
When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...
What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?
Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...
Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?
Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...
How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?
Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...
What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...
Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?
There are alternative reagents and compounds that can be used in the synthesis o...
What is Tungsten(IV) oxide (CAS: 12036-22-5)?
Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...
Source Journal
Natural Product Reports

Natural Product Reports (NPR) is a critical review journal that stimulates progress in all areas of natural products research, including isolation, structural and stereochemical determination, biosynthesis, biological activity and synthesis. The scope of the journal is very broad, and many reviews discuss the role of natural products in the wider bioinorganic, bioorganic and chemical biology communities. Areas covered include the following: Enzymology Nucleic acids Genetics Chemical ecology Carbohydrates Primary and secondary metabolism Analytical techniques NPR articles are designed to give an interesting insight into the topic, focusing on the key developments that have shaped a field. Authors are encouraged to include their own perspective on developments, trends and future directions. Articles providing a very comprehensive overview or exhaustive list of previous literature and lacking critical insight are generally not suitable for publication in NPR. Meta-analyses of previously published data using existing tools can be included, however NPR articles should not include any new methods or data.













![2-{3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one hydrochloride (1:1) structure 2-{3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one hydrochloride (1:1) structure](https://static.chemtradehub.com/structs/253/25332-39-2-496e.webp)
