13010-53-2

Basic information

• Product Name: L-METHIONINE-METHYL-D3
• Synonyms: L-METHIONINE-D3;L-METHIONINE-D3 (S-METHYL-D3);L-METHIONINE-METHYL-D3;L-METHIONINE-METHYL-D3, 98 ATOM % D;l-methionine-d3(methyl-d3);(S)-2-AMino-4-(Methylthio-d3)butanoic Acid;FFEARJCKVFRZRR-OSIBIXDNSA-N
• CAS NO: 13010-53-2
• Molecular Formula: C₅H₁₁NO₂S
• Molecular Weight: 152.23
• Product Categories: Metabolic Research;Alphabetical Listings;Amino Acids;Amino AcidsStable Isotopes;Biomolecular MS;Metabolic Labeling Products;MStable Isotopes;Stable Isotopes;Amino Acids & Derivatives;Isotope Labelled Compounds;Sulfur & Selenium Compounds
• Mol File: 13010-53-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 273 °C (dec.)(lit.)
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Aqueous Acid (Sparingly), Water (Slightly, Heated)
• CAS DataBase Reference: L-METHIONINE-METHYL-D3(CAS DataBase Reference)
• NIST Chemistry Reference: L-METHIONINE-METHYL-D3(13010-53-2)
• EPA Substance Registry System: L-METHIONINE-METHYL-D3(13010-53-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13010-53-2(Hazardous Substances Data)

Usage

Description

L-Methionine-methyl-d3 is a stable isotope-labeled form of the essential amino acid L-Methionine. It is characterized by the presence of deuterium (D), a hydrogen isotope, at the methyl group. This stable isotope labeling allows for the differentiation and tracking of L-Methionine-methyl-d3 in various biological processes and research applications.

Uses

Used in Human Development:
L-Methionine-methyl-d3 is used as an essential amino acid for human development, playing a crucial role in the growth and maintenance of tissues and cells.
Used in Hepatoprotection:
L-Methionine-methyl-d3 is used as a hepatoprotectant, which means it helps protect the liver from damage and supports its overall health.
Used in Antidote for Acetaminophen Poisoning:
L-Methionine-methyl-d3 is used as an antidote for acetaminophen poisoning, aiding in the detoxification process and reducing the risk of liver damage.
Used in Urinary Acidification:
L-Methionine-methyl-d3 is used as a urinary acidifier, which helps regulate the pH level of urine and can be beneficial for certain medical conditions.
Used in Research and Diagnostics:
L-Methionine-methyl-d3 is used as a stable isotope tracer in research and diagnostics, allowing for the tracking and analysis of metabolic pathways and biochemical processes involving L-Methionine.
Used in Pharmaceutical Industry:
L-Methionine-methyl-d3 is used as a labeled compound in the pharmaceutical industry for the development and testing of new drugs, as well as for quality control and assurance purposes.
Used in Nutritional Supplements:
L-Methionine-methyl-d3 is used as an ingredient in nutritional supplements, providing a stable isotope-labeled source of the essential amino acid for various health and performance benefits.
Chemical Properties:
L-Methionine-methyl-d3 is a white solid, which is a common physical form for many amino acids and their derivatives.

Synthetic route

C9H17(2)H3NO2S(1+)*C7H7O3S(1-) → L-2H3>methionine (13010-53-2)

L-2H3>methionine (13010-53-2) + ATP (56-65-5) → S-adenosyl-L-[methyl-2H3]methionine (68684-40-2)

Conditions	Yield
With pyrophosphatase; ethylenediaminetetraacetic acid; AdoMet synthetase lysate; tris hydrochloride; 2-hydroxyethanethiol at 25℃; pH=8.0;	87.9%
With SAM synthetase overexpressed by E. coli strain DM22-(pK8); magnesium chloride In acetonitrile at 20℃; for 5h; pH=8; Enzymatic reaction;

L-2H3>methionine (13010-53-2) → 22-dihydrochondrillasterol (521-03-9, 6869-99-4, 18525-35-4, 18725-34-3, 21632-38-2) + 22-dihydro-25-dehydrochondrillasterol (6785-58-6, 18070-04-7, 34350-87-3, 54323-81-8, 62741-94-0)

Conditions	Yield
With Trichosanthes kirilowii In water for 240h; Mechanism;	A 0.8 mg B 0.4 mg

L-2H3>methionine (13010-53-2) + Trichosanthes kirilowii → 22-dihydrochondrillasterol (521-03-9, 6869-99-4, 18525-35-4, 18725-34-3, 21632-38-2) + 22-dihydro-25-dehydrochondrillasterol (6785-58-6, 18070-04-7, 34350-87-3, 54323-81-8, 62741-94-0)

Conditions	Yield
In water for 240h;	A 0.8 mg B 0.4 mg

L-2H3>methionine (13010-53-2) + Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm., isolate Maifair 2 → C14H6(2)H12O3

Conditions	Yield
With minimal essential medium for 144h;

L-glutamine (56-85-9) + L-2H3>methionine (13010-53-2) → [2H3-Me]-γ-glutamyl-L-methionine

Conditions	Yield
With Penicillium roquefortii 1812 In water at 25℃; for 480h; Enzymatic reaction;

carbon dioxide (124-38-9) + L-2H3>methionine (13010-53-2) → C19H20(2)H3N6O11P

Conditions	Yield
Stage #1: carbon dioxide; L-2H3>methionine With hydrogen at 65℃; pH=6; Microbiological reaction; aq. mineral salt medium; Stage #2: With ammonia; 2-hydroxyethanethiol In methanol; water at 40℃; for 0.25h; Inert atmosphere; Stage #3: With water Photolysis; Cooling with ice; Alkaline conditions;

L-2H3>methionine (13010-53-2) + 5'-deoxy-5'-chloroadenosine (892-48-8) → S-adenosyl-L-[methyl-d3]-methionine

Conditions	Yield
With enzyme SalL (Salinospora tropica); Cleland's reagent; BSA In aq. phosphate buffer at 37℃; for 7h; pH=6.5; Enzymatic reaction;

L-2H3>methionine (13010-53-2) + C10H12(2)H4N5O13P3 → CD3-5′,5′,4′,3′-D4-SAM

Conditions	Yield
With SAM synthetase overexpressed by E. coli strain DM22-(pK8); magnesium chloride In acetonitrile at 20℃; for 5h; pH=8; Enzymatic reaction;

Upstream product

• 865-50-9 iodomethane-d3 
• 18265-50-4 DL-homocysteine thiolactone hydrochloride 

Downstream Products

• 521-03-9 22-dihydrochondrillasterol 
• 6785-58-6 22-dihydro-25-dehydrochondrillasterol 

Relevant articles and documents

Biosynthetic Studies of Marine Lipids. 4. Mechanism of Side Chain Alkylation in (E)-24-Propylidenecholesterol by a Chrysophyte Alga

A photosynthetic marine Chrysophyte (unicellular alga) was cultured in a medium containing labeled methionine (methyl-13C, methyl-d3).The 2H and 13C distribution in the alkyl substituents of the sterols was determined by 2H and 13C NMR.Although two novel cyclopropyl sterols - (24R,28R)- and (24S,28R)-24,28-methylene-5-stigmasten-3β-ol - and their ring opening products were found as trace sterols in the alga, the results of 2H NMR indicate that the substituent in the side chain of the main sterol ((E)-24-propylidenecholesterol) is not formed by ring opening of these cyclopropyl sterols.Instead, the main sterol is most likely formed by further alkylation of a 24-vinyl sterol which has so far not been been encountered in nature.Other novel sterols encountered in the Chrysophyte belong to the rare classes of Δ23, 14α-methyl, and Δ8(14),15-diene sterols.

Synthetic method of stable isotope deuterium-labeled alpha-amino acid

The invention relates to a synthetic method of stable isotope deuterium-labeled alpha-amino acid. According to the method, one or more deuterium-labeled halides are taken as labeled precursors and subjected to a reaction with phthalimide dimethyl malonate sodium salt, one or more deuterium-substituted phthalimide dimethyl malonate is obtained, and after hydrolysis, stable isotope deuterium-labeledalpha-amino acid is obtained. Compared with the prior art, the synthetic method is simple, safe and reliable, chemical purity of a product after simple separation and purification reaches 99% or higher, isotope abundance is 99% or higher, and the method can be applied to fields of protein metabolism tracing, food safety testing and the like.

Homocysteine thiolactone as precursor of methionine amide: Application to the modification of peptides of the tachykinin family

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