N-Methyl-L-methionine
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| Category | Others |
| Catalog number | BBF-05245 |
| CAS | 42537-72-4 |
| Molecular Weight | 163.24 |
| Molecular Formula | C6H13NO2S |
| Purity | >95% by HPLC |
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Specification
| Related CAS | 526210-74-2 (D-configuration) |
| Synonyms | N-Me-Met-OH; S-methylmethionine; (S)-N-methylmethionine; L-Methionine, N-methyl-; H-N-Me-Met-OH; (S)-Z-N-methylmethionine; methyl-L-methionine |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-(methylamino)-4-methylsulfanylbutanoic acid |
| Canonical SMILES | CNC(CCSC)C(=O)O |
| InChI | InChI=1S/C6H13NO2S/c1-7-5(6(8)9)3-4-10-2/h5,7H,3-4H2,1-2H3,(H,8,9)/t5-/m0/s1 |
| InChI Key | YAXAFCHJCYILRU-YFKPBYRVSA-N |
Properties
| Boiling Point | 302.7±37.0°C (Predicted) |
| Melting Point | 255-257°C |
| Density | 1.122±0.06 g/cm3 (Predicted) |
Reference Reading
1. Methionine deficiency facilitates antitumour immunity by altering m6A methylation of immune checkpoint transcripts
Ting Li, Yue-Tao Tan, Yan-Xing Chen, Xiao-Jun Zheng, Wen Wang, Kun Liao, Hai-Yu Mo, Junzhong Lin, Wei Yang, Hai-Long Piao, Rui-Hua Xu, Huai-Qiang Ju Gut. 2023 Mar;72(3):501-511. doi: 10.1136/gutjnl-2022-326928. Epub 2022 Jul 8.
Objective: Methionine metabolism is involved in a myriad of cellular functions, including methylation reactions and redox maintenance. Nevertheless, it remains unclear whether methionine metabolism, RNA methylation and antitumour immunity are molecularly intertwined. Design: The antitumour immunity effect of methionine-restricted diet (MRD) feeding was assessed in murine models. The mechanisms of methionine and YTH domain-containing family protein 1 (YTHDF1) in tumour immune escape were determined in vitro and in vivo. The synergistic effects of MRD or YTHDF1 depletion with PD-1 blockade were also investigated. Results: We found that dietary methionine restriction reduced tumour growth and enhanced antitumour immunity by increasing the number and cytotoxicity of tumour-infiltrating CD8+ T cells in different mouse models. Mechanistically, the S-adenosylmethionine derived from methionine metabolism promoted the N6-methyladenosine (m6A) methylation and translation of immune checkpoints, including PD-L1 and V-domain Ig suppressor of T cell activation (VISTA), in tumour cells. Furthermore, MRD or m6A-specific binding protein YTHDF1 depletion inhibited tumour growth by restoring the infiltration of CD8+ T cells, and synergised with PD-1 blockade for better tumour control. Clinically, YTHDF1 expression correlated with poor prognosis and immunotherapy outcomes for cancer patients. Conclusions: Methionine and YTHDF1 play a critical role in anticancer immunity through regulating the functions of T cells. Targeting methionine metabolism or YTHDF1 could be a potential new strategy for cancer immunotherapy.
2. Insights into methionine S-methylation in diverse organisms
Ming Peng, Chun-Yang Li, Xiu-Lan Chen, Beth T Williams, Kang Li, Ya-Nan Gao, Peng Wang, Ning Wang, Chao Gao, Shan Zhang, Marie C Schoelmerich, Jillian F Banfield, J Benjamin Miller, Nick E Le Brun, Jonathan D Todd, Yu-Zhong Zhang Nat Commun. 2022 May 26;13(1):2947. doi: 10.1038/s41467-022-30491-5.
Dimethylsulfoniopropionate (DMSP) is an important marine anti-stress compound, with key roles in global nutrient cycling, chemotaxis and, potentially, climate regulation. Recently, diverse marine Actinobacteria, α- and γ-proteobacteria were shown to initiate DMSP synthesis via the methionine (Met) S-methyltransferase enzyme (MmtN), generating S-methyl-Met (SMM). Here we characterize a roseobacterial MmtN, providing structural and mechanistic insights into this DMSP synthesis enzyme. We propose that MmtN uses the proximity and desolvation mechanism for Met S-methylation with two adjacent MmtN monomers comprising the Met binding site. We also identify diverse functional MmtN enzymes in potentially symbiotic archaeal Candidatus Woesearchaeota and Candidate Phyla Radiation (CPR) bacteria, and the animalcule Adineta steineri, not anticipated to produce SMM and/or DMSP. These diverse MmtN enzymes, alongside the larger plant MMT enzyme with an N-terminus homologous to MmtN, likely utilize the same proximity and desolvation mechanism. This study provides important insights into the catalytic mechanism of SMM and/or DMSP production, and proposes roles for these compounds in secondary metabolite production, and SMM cycling in diverse organisms and environments.
3. [Analogs of S-Adenosyl-L-Methionine in Studies of Methyltransferases]
A Yu Rudenko, S S Mariasina, P V Sergiev, V I Polshakov Mol Biol (Mosk). 2022 Mar-Apr;56(2):296-319. doi: 10.31857/S0026898422020148.
Methyltransferases (MTases) play an important role in the functioning of living systems, catalyzing the methylation reactions of DNA, RNA, proteins, and small molecules, including endogenous compounds and drugs. Many human diseases are associated with disturbances in the functioning of these enzymes; therefore, the study of MTases is an urgent and important task. Most MTases use the cofactor S-adenosyl-L-methionine (SAM) as a methyl group donor. SAM analogs are widely applicable in the study of MTases: they are used in studies of the catalytic activity of these enzymes, in identification of substrates of new MTases, and for modification of the substrates or substrate linking to MTases. In this review, new synthetic analogs of SAM and the problems that can be solved with their usage are discussed.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
