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3211-76-5

中文名稱 (S)-(+)-2-氨基-4-(甲基硒)丁酸
英文名稱 L-Selenomethionine
CAS 3211-76-5
分子式 C5H11NO2Se
MDL 編號 MFCD00037210
分子量 196.11
MOL 文件 3211-76-5.mol
更新日期 2025/08/07 09:27:50
3211-76-5 結(jié)構(gòu)式 3211-76-5 結(jié)構(gòu)式

基本信息

中文別名
L(+)硒代蛋氨酸
硒代蛋氨酸
L-(+)-硒代蛋氨酸
(S)-(+)-2-氨基-4-(甲基硒)丁酸
英文別名
2-AMINO-4-(METHYLSELENO)BUTANOIC ACID
L-(+)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID
L-(+)-SELENOMETHIONINE
L-SELENOMETHIONINE
(S)-(+)-2-AMINO-4-(METHYLSELENO)BUTANOIC ACID
(S)-2-AMINO-4-(METHYLSELENO)BUTYRIC ACID
SELENO-L-METHIONINE
SELENOMETHIONINE, L-(+)-
SEMET
L(+)-SELENOMETHIONINE 99+% E.E.
(S)-2-AMINO-4-(METHYLSELENYL)BUTYRIC ACID
L(+)-Selenomethionine, ee 99+%, 99+%
Butanoic acid, 2-amino-4-(methylseleno)-, (2S)-
L-SELENOMETHIONINE SELENO-L-METHIONINE L-SE-MET-OH
L-selenomethionine (L-se-Met-OH)
BUTYRICACID,2-AMINO-4-(METHYLSELENYL)-,L-
L-SELENOMETHIONINE 0.5%
L-SELENOMETHIONINE USP
THALLIUM ETHYLSUFATE
(S)-(+)-2-Amino-4-(methylseleno)butanoic acid, (S)-2-Amino-4-(methylseleno)butyric acid, L-Selenomethionine, Seleno-L-methionine
所屬類別
生物化工:其他氨基酸衍生物

物理化學性質(zhì)

熔點265 °C
比旋光度18 º (c=1, 1N HCl)
沸點320.8±37.0 °C(Predicted)
折射率18 ° (C=0.5, 2mol/L HCl)
儲存條件−20°C
溶解度H2O: 50 mg/mL
酸度系數(shù)(pKa)2.26±0.10(Predicted)
形態(tài)powder
顏色white to off-white
水溶解性可溶于水
Merck8441
InChIInChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
InChIKeyRJFAYQIBOAGBLC-BYPYZUCNSA-N
SMILESC(O)(=O)[C@@H](N)CC[Se]C
LogP0.152 (est)
CAS 數(shù)據(jù)庫3211-76-5(CAS DataBase Reference)

安全數(shù)據(jù)

危險性符號(GHS)GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08,GHS09
警示詞危險
危險性描述H301+H331-H373-H410
危險品標志T,N
危險類別碼R23/25-R33-R50/53
危險品運輸編號UN 3283 6.1/PG 2
WGK Germany3
RTECS號EK7713840
危險等級6.1
包裝類別III
海關(guān)編碼29309090

應(yīng)用領(lǐng)域

用途一
可以用于蛋白質(zhì)的結(jié)構(gòu)分析。拿此產(chǎn)品來飼養(yǎng)細菌,這樣最終形成的蛋白質(zhì)里的特定位置就會被硒所取代,便于結(jié)構(gòu)測定

制備方法

方法1
L-高絲氨酸內(nèi)酯鹽酸鹽

2185-03-7

Methaneselenol, sodium salt (9CI)

37773-10-7

L-硒代蛋氨酸

3211-76-5

在氮氣保護下,將13.75 g L-高絲氨酸內(nèi)酯鹽酸鹽與40 mL N,N-二甲基甲酰胺(DMF)混合,攪拌至完全溶解。隨后,將15.2 g硒酸甲酯(CAS:37773-10-7)溶于20 mL DMF中,緩慢加入上述反應(yīng)體系。加熱回流反應(yīng)2小時。反應(yīng)完成后,用乙酸水溶液調(diào)節(jié)反應(yīng)體系的pH至6.0,析出白色固體。將所得固體溶于水和乙醇的混合溶劑中進行重結(jié)晶,得到L-硒代蛋氨酸。該合成路線的總收率為72.11%,產(chǎn)物的化學純度大于99%,對映體過量值(ee)大于99%。

參考文獻:

[1] Patent: CN106928110, 2017, A. Location in patent: Paragraph 0028; 0030

化學品安全說明書(MSDS)

L-硒代蛋氨酸價格(試劑級)
報價日期產(chǎn)品編號產(chǎn)品名稱CAS號包裝價格
2025/05/2225996L(+)硒代蛋氨酸
L(+)-Selenomethionine, 99+%, ee 99+%
3211-76-5250mg3125元
2025/05/2225996L(+)硒代蛋氨酸
L(+)-Selenomethionine, 99+%, ee 99+%
3211-76-51g8402元
2025/05/2225996L(+)硒代蛋氨酸
L(+)-Selenomethionine, 99+%, ee 99+%
3211-76-52.5g14456元

常見問題列表

生物活性
L-SelenoMethionine 是 Selenomethionine 的 L-異構(gòu)體,是硒的主要天然食物形式。L-SelenoMethionine 是一種癌癥化學預(yù)防劑,可以通過飲食補充降低癌癥的發(fā)生率并誘導癌細胞凋亡。L-SelenoMethionine 還可以增加谷胱甘肽過氧化物酶的表達。
靶點

Human Endogenous Metabolite

體外研究

L-SelenoMethionine (1-500 μM; 24-72 h) is selectively inhibits the growth of prostate cancer cells, compared with normal cells.
L-SelenoMethionine (500 μM; 48 h) induce apoptosis in prostate cancer cells.
L-SelenoMethionine (500 μM; 48 h) causes an increase in arrest in the G2-M phase of the cell cycle selectively in prostate cancer cells.
L-SelenoMethionine (5 μM; 24 h) mitigates gene expression associated with the cellular stress response from 10 cGy irradiation.

Cell Viability Assay

Cell Line: Prostate cancer cells (LNCaP, PC-3, and DU145) and normal prostate cells (PrEC, PrSM, and PrSt)
Concentration: 1, 5, 10, 50, 100, 500 μM
Incubation Time: 24, 48, 72 hours
Result: Inhibited the growth of prostate cancer cells, with a lower IC 50 (1-90 μM) at 72 h than normal prostate cells (>500 μM).

Apoptosis Analysis

Cell Line: Prostate cancer cells (LNCaP, PC-3, and DU145) and normal prostate cells (PrEC, PrSM, and PrSt)
Concentration: 500 μM
Incubation Time: 48 hours
Result: Exhibited the highest level of DNA condensation in androgen-responsive LNCaP carcinoma cells, followed by PC-3 and DU145 cells.
Exhibited the nicked-end DNA labeling in prostate cancer cells.
Promoted the PARP cleavage in prostate cancer cells.

Cell Cycle Analysis

Cell Line: Prostate cancer cells (LNCaP, PC-3, and DU145) and normal prostate cells (PrEC, PrSM, and PrSt)
Concentration: 500 μM
Incubation Time: 48 hours
Result: Increased the sub-G0-G1 cell fraction of LNCaP (41.5%), PC-3 (12.1%), and DU145 cells (11.2%).
Caused a significant increases in G2 cells , particularly in LNCaP (13%), PC-3 (32%), and DU145 (20%) cells.

RT-PCR

Cell Line: Human thyroid epithelial cells (HTori-3)
Concentration: 5 μM
Incubation Time: 24 hours
Result: Downregulated the CDC6, GADD45A, FAS and ATF3 in irradiated cells.
體內(nèi)研究

L-SelenoMethionine (0.06-12 μg/g diet; p.o. for 3 d) partially or completely prevent the decrease in the serum or plasma levels of total antioxidants in rats exposed to gamma rays, protons or HZE particles.

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