3211-76-5

Basic information

• Product Name: L-(+)-Selenomethionine
• Synonyms: (S)-(+)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID;(S)-2-AMINO-4-(METHYLSELENO)BUTYRIC ACID;SEMET;SELENOMETHIONINE, L-(+)-;SELENO-L-METHIONINE;L-(+)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID;L-(+)-SELENOMETHIONINE;L-SELENOMETHIONINE
• CAS NO: 3211-76-5
• Molecular Formula: C₅H₁₁NO₂Se
• Molecular Weight: 196.11
• EINECS: 2017-001-1
• Product Categories: Amino Acid Derivatives;Methionine [Met, M];Amino Acids;Antioxidant;Biochemistry;Biological-modified Amino Acids;Classes of Metal Compounds;Se (Selenium) Compounds;Semimetal Compounds;Seleno Amino Acid;amino acid
• Mol File: 3211-76-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 265 °C
• Boiling Point: 320.78 °C at 760 mmHg
• Flash Point: 147.803 °C
• Appearance: white to off-white/powder
• Refractive Index: 18 ° (C=0.5, 2mol/L HCl)
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL
• PKA: 2.26±0.10(Predicted)
• Water Solubility: soluble
• Merck: 14,8441
• CAS DataBase Reference: L-(+)-Selenomethionine(CAS DataBase Reference)
• NIST Chemistry Reference: L-(+)-Selenomethionine(3211-76-5)
• EPA Substance Registry System: L-(+)-Selenomethionine(3211-76-5)

Safety Data

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61-28A
• RIDADR: UN 3283 6.1/PG 2
• WGK Germany: 3
• RTECS: EK7713840
• F: 10
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3211-76-5(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 3211-76-5 differently. You can refer to the following data:
1. A compound shown to increase expression of glutathione peroxidase
2. Seleno-L-methionine has been used: in toxicity studies in Japanese Medaka embryosto study its effects on selenium status indicators in pregnant long-tailed macaques (Macaca Fascicularis)to label proteins for single wavelength anomalous dispersion (SAD) phasing

Definition

ChEBI: The L-enantiomer of selenomethionine.

General Description

Seleno-L-Methionine (SeMet), an organic form of selenium is found in Cupriavidus metallidurans.

Biochem/physiol Actions

Seleno-L-Methionine (SeMet) is capable of repressing atopic dermatitis (AD)-like skin lesions. It can also prevent the expression of total immunoglobulin E (IgE) and interleukin 4 (IL-4). It can cause ecotoxicity as it is absorbed by fish through diet.

InChI:InChI=1/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

Synthetic route

N-Boc-L-selenomethionine (45172-44-9) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.5h; Ambient temperature;	96%

sodium methylselenide (37773-10-7) + (3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide (3493-11-6) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
In methanol; ethanol at 45℃; for 9h; Solvent; Temperature; Inert atmosphere;	82%

dimethyl sulfate (77-78-1) + L,L-selenohomocystine → Seleno-L-methionine (3211-76-5)

Conditions	Yield
Stage #1: L,L-selenohomocystine With sodium tetrahydroborate; ethanol at 30 - 45℃; for 5h; Inert atmosphere; Stage #2: dimethyl sulfate at 25 - 30℃; for 3h; Temperature;	81.8%

methyllithium (917-54-4) + α-amino-γ-bromobutyric acid methyl ester hydrochloride (15159-66-7) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
Stage #1: methyllithium; α-amino-γ-bromobutyric acid methyl ester hydrochloride With selenium; boric acid tributyl ester In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at -78 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide for 0.166667h; Temperature; Reagent/catalyst;	66%

(S)-2-Benzyloxycarbonylamino-4-methylselanyl-butyric acid; compound with dicyclohexyl-amine → Seleno-L-methionine (3211-76-5)

Conditions	Yield
(i) aq. H2SO4, AcOEt, (ii) HBr, HSCH2CH2OH, AcOH; Multistep reaction;

(2S)-2-amino-4-(benzylselanyl)butanoic acid (19635-25-7) + methyl iodide (74-88-4) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
(i) Na, liq. NH3, (ii) /BRN= 969135/, NH4Cl; Multistep reaction;

Lithium; 2-acetylamino-4-methylselanyl-butyrate → Seleno-L-methionine (3211-76-5)

Conditions	Yield
at 39℃; aminoacylase;

2-Acetylamino-4-methylselanyl-butyric acid (174463-50-4) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With acylase from Aspergillus oryzae; water at 20 - 37℃;

N-Acetylseleno-L-methionine → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With pig kidney acylase I In phosphate buffer at 37℃; for 0.166667h; pH=7.4; Enzyme kinetics; Deacetylation;

L-selenohomocysteine (29475-60-3) + N-[4-[[(2-amino-1,4,5,6,7,8,-hexahydro-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamate → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With E. coli cobalamin-independent methionine synthase (2-649) Enzyme kinetics; Methylation;

L-selenohomocysteine (29475-60-3) + methylcobalamin → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With E. coli cobalamin-dependent methionine synthase (2-649) Enzyme kinetics; Methylation;

seleno-DL-methionine (2578-28-1) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84.1 percent / 4 h / 15 - 30 °C 2: H2O, acylase from Aspergillus oryzae / 20 - 37 °C View Scheme

L-benzyl N-t-butoxycarbonylselenomethioninate (109276-72-4) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NaOH / dioxane; H2O / 0.5 h / Ambient temperature 2: 96 percent / trifluoroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

L-selenomethionine methyl ester hydrochloride → Seleno-L-methionine (3211-76-5)

Conditions	Yield
In methanol; water at 20℃; for 0.166667h; Alkaline conditions;

L-homoserine lactone hydrochloride (2185-03-7) + sodium methylselenide (37773-10-7) → Seleno-L-methionine (3211-76-5)

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	n/a

C13H17NO4Se → Seleno-L-methionine (3211-76-5)

Conditions	Yield
With hydrogen bromide In tetrahydrofuran; 1,4-dioxane Inert atmosphere; Green chemistry;	8.99 g

dimethyl sulfoxide (67-68-5) + L,L-selenohomocystine → Seleno-L-methionine (3211-76-5)

Conditions	Yield
Stage #1: L,L-selenohomocystine With sodium tetrahydroborate; ethanol at 35℃; for 5h; Inert atmosphere; Stage #2: dimethyl sulfoxide at 45℃; for 1.5h; Temperature; Reagent/catalyst; Inert atmosphere;	43.4 g

di-tert-butyl dicarbonate (24424-99-5) + Seleno-L-methionine (3211-76-5) → N-Boc-L-selenomethionine (45172-44-9)

Conditions	Yield
Stage #1: Seleno-L-methionine With sodium hydrogencarbonate In 1,4-dioxane; water for 0.333333h; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 13h; Cooling with ice;	98%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 20h;
With sodium hydrogencarbonate In 1,4-dioxane; water at 25℃;
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 12h;

Seleno-L-methionine (3211-76-5) + 2,4-Dinitrofluorobenzene (70-34-8) → N-(2,4-dinitrophenyl)seleno-L-methionine (919767-00-3)

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20 - 40℃; for 9h;	90%

formic acid (64-18-6) + Seleno-L-methionine (3211-76-5) → N-formyl selenomethionine

Conditions	Yield
With acetic anhydride for 1h;	88%

Seleno-L-methionine (3211-76-5) → L-selenomethionine Se-oxide

Conditions	Yield
With dihydrogen peroxide for 0.25h; cooling;	85%
With Sprague-Dawley rat liver microsomes; NADPH; catalase In phosphate buffer for 0.333333h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents;
With dihydrogen peroxide In water

Seleno-L-methionine (3211-76-5) + 2-(acetylmethylseleno)benzoyl chloride → 2-(2-acetonylselenobenzamide)-4-methylselenobutyric acid

Conditions	Yield
In acetone at 0℃; for 8.5h;	85%

succinic acid anhydride (108-30-5) + Seleno-L-methionine (3211-76-5) → (S)-4-(1-carboxy-3-(methylselanyl)propylamino)-4-oxobutanoic acid (918887-82-8)

Conditions	Yield
With sulfuric acid In water; ethyl acetate for 1h; Heating / reflux;	84.14%

Seleno-L-methionine (3211-76-5) → N-carbamoyl L-selenomethionine

Conditions	Yield
Stage #1: Seleno-L-methionine With potassium cyanate In water at 80 - 94℃; for 2h; Stage #2: With hydrogenchloride In water at 20℃;	83.65%

Seleno-L-methionine (3211-76-5) + 2,2-dimethoxy-propane (77-76-9) → L-selenomethionine methyl ester hydrochloride

Conditions	Yield
With hydrogenchloride for 18h;	83%

copper(II) nitrate trihydrate + Seleno-L-methionine (3211-76-5) → Cu(L-selenomethionine)2

Conditions	Yield
With sodium hydroxide In water pH=6;	78%

1-ethoxy-4-iodobenzene (699-08-1) + Seleno-L-methionine (3211-76-5) → 1-Ethoxy-4-methylselanyl-benzene (86297-06-5)

Conditions	Yield
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 12h;	78%

n-dodecanoyl chloride (112-16-3) + Seleno-L-methionine (3211-76-5) → N-lauroyl-L-selenomethionine

Conditions	Yield
Stage #1: Seleno-L-methionine With potassium hydroxide Sonication; Cooling with ice; Stage #2: n-dodecanoyl chloride In tetrahydrofuran at 50℃; for 4h; pH=12; Temperature; pH-value; Cooling with ice;	77.34%

Seleno-L-methionine (3211-76-5) + 5'-deoxy-5'-chloroadenosine (892-48-8) → Se-adenosyl-L-selenohomocysteine (4053-91-2)

Conditions	Yield
Stage #1: Seleno-L-methionine With ammonia; sodium at -35℃; for 1.25h; Inert atmosphere; Stage #2: 5'-deoxy-5'-chloroadenosine In methanol at 50℃; for 24h; Inert atmosphere;	74%

Seleno-L-methionine (3211-76-5) + 5'-chloro-5'-deoxyadenosine → Selenoadenosylhomocysteine

Conditions	Yield
at 50℃; for 24h; Cooling with acetone-dry ice; Inert atmosphere;	74%

Seleno-L-methionine (3211-76-5) + 5'-deoxy-5'-chloroadenosine (892-48-8) → (2R)-2-amino-4-((((2S,3S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)selanyl)butanoic acid

Conditions	Yield
Stage #1: Seleno-L-methionine With ammonia; sodium Inert atmosphere; Cooling with acetone-dry ice; Stage #2: 5'-deoxy-5'-chloroadenosine In methanol at 50℃; for 24h; Inert atmosphere;	74%

(Z)-9-octadecenoyl chloride (112-77-6) + Seleno-L-methionine (3211-76-5) → N-oleoyl-L-selenomethionine

Conditions	Yield
Stage #1: Seleno-L-methionine With potassium hydroxide Sonication; Cooling with ice; Stage #2: (Z)-9-octadecenoyl chloride In tetrahydrofuran at 25℃; for 2h; pH=9 - 10; Cooling with ice;	68.77%

Seleno-L-methionine (3211-76-5) → L-selenohomocysteine (29475-60-3)

Conditions	Yield
With ammonia; sodium at -78℃; for 1.33333h;	62%
With ammonia; sodium at -80℃; for 0.833333h; demethylation;
With ammonia; sodium at -80℃; for 1h; Inert atmosphere; Darkness;
With ammonia; sodium at -60℃; for 1h;

Seleno-L-methionine (3211-76-5) + isopropyl alcohol (67-63-0) → L-selenomethionine isopropyl ester

Conditions	Yield
Stage #1: Seleno-L-methionine; isopropyl alcohol With sulfuric acid at 0℃; for 48h; Heating / reflux; Stage #2: With ammonia In water; isopropyl alcohol	52.61%

Seleno-L-methionine (3211-76-5) + 4-chlorobenzaldehyde (104-88-1) + tert-butylamine (75-64-9) → (2S)-2-(((1-(tert-butyl)-1H-tetrazol-5-yl)(4-chlorophenyl)methyl)amino)-4-(methylselanyl)butanoic acid

Conditions	Yield
Stage #1: Seleno-L-methionine; 4-chlorobenzaldehyde In methanol at 20℃; for 0.166667h; Ugi Condensation; Stage #2: tert-butylamine With sodium azide In methanol at 20℃; for 12h; Ugi Condensation;	51%

Seleno-L-methionine (3211-76-5) + methylmercury(II) hydroxide (1184-57-2) → methylmercury-L-selenomethioninate

Conditions	Yield
With HNO3 In water byproducts: Se; Se-compound added to H2O, pH adjusted by HNO3 to 0.5, CH3HgOH added, stirred for 3.5 h; filtered, solvent evapd. in vac., kept under Ar at 4°C; elem. anal.;	49%

Seleno-L-methionine (3211-76-5) + benzyl bromide (100-39-0) → (2S)-2-amino-4-(benzylselanyl)butanoic acid (19635-25-7) + L-selenohomocysteine (29475-60-3)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	A 7% B 38%

Seleno-L-methionine (3211-76-5) + isopropyl bromide (75-26-3) → (2S)-2-amino-4-(propan-2-ylselanyl)butanoic acid (1601474-76-3)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	9%
With hydrogenchloride In water at 100℃; for 12h;	9%

Seleno-L-methionine (3211-76-5) + benzyl bromide (100-39-0) → (2S)-2-amino-4-(benzylselanyl)butanoic acid (19635-25-7)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	7%

Upstream product

• 29475-60-3 L-selenohomocysteine 
• 2185-03-7 L-homoserine lactone hydrochloride 
• 37773-10-7 sodium methylselenide 
• 3493-11-6 (3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide 
• 6486-05-1 methyl selenide 
• 127628-31-3 (l)α-amino-γ-butyrolactone hydroiodide 
• 1192-20-7 (l)α-amino-γ-butyrolactone 
• 7101-31-7 dimethyl diselenide 
• 77-78-1 dimethyl sulfate 
• 67-68-5 dimethyl sulfoxide 
• 917-54-4 methyllithium 
• 15159-66-7 α-amino-γ-bromobutyric acid methyl ester hydrochloride 
• 109276-72-4 L-benzyl N-t-butoxycarbonylselenomethioninate 
• 2578-28-1 seleno-DL-methionine 

Downstream Products

• 45172-44-9 N-Boc-L-selenomethionine 
• 5134-38-3 C₁₅H₂₂N₆O₅Se 
• 5135-40-0 (2R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((methylselanyl)methyl)tetrahydrofuran-3,4-diol 
• 19635-25-7 (2S)-2-amino-4-(benzylselanyl)butanoic acid 

Relevant articles and documents

A new efficient synthesis of acetyltelluro- and acetylselenomethionine and their use in the biosynthesis of heavy-atom protein analogs

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Synthetic method of L-selenomethionine

The invention discloses a synthetic method of L-selenomethionine, and belongs to the field of additives. The synthetic method comprises the following steps: A, a compound 1 and a compound 2 react in asolvent, and filtering and drying are carried out after a reaction is completed, and then a green solid compound 3 is obtained; and B, the compound 3 and sodium borohydride react in a protonic solvent for 1-10 h, after a reaction is completed, dimethyl sulfate is dropwise added to continue to react for 1-5 h, then quenching through acetic acid and filtering are conducted, and thus the L-selenomethionine is prepared. The synthetic method has the beneficial effects that 1, it is reported in the literature that the compound 1 is mild in condition and high in yield; 2, the compound 2 is mild in reaction condition, no highly toxic and foul sodium methyl selenide is generated, and labor protection and environmental protection are facilitated; 3, the compound 2 is easy to separate only through centrifugal spinning-filtration, and an obtained product is high in purity; and 4, adopted raw materials and reagents are all commercially available, in the preparation process of the L-selenomethionine, intermediates do not need to be separated, and operation is easy.

Method for synthesizing L L-(+)-selenomethionine (by machine translation)

The synthetic route disclosed L - (+) - by the invention has, L - (+) - the advantages that the raw materials, are easy to obtain, the reaction conditions are, mild, the reaction conditions are mild, the separation, and purification are easy, L - (+) - and the; method L - (+) - is easy, to separate and purify L - (+) - L - (+) - L - (+) . (by machine translation)