29908-03-0 Usage
description
S-Adenosyl-L-methionine (also called S-adenosyl methionine, S-adenosylmethionine, SAMe, or SAM-e in the United States or ademetionine in Europe, and also often abbreviated as SAM and AdoMet) is a chemical that is found naturally in the body. SAMe is sold in the United States as a dietary supplement.
S-Adenosyl-L-methionine was discovered in the early 1950s. It’s made in the body from methionine, an amino acid found in foods. It has been found to regulate key functions in living cells.
Abnormal levels of S-Adenosyl-L-methionine in the body have been reported in liver diseases and depression. This prompted researchers to investigate whether S-Adenosyl-L-methionine might be helpful in treating these conditions. The idea that S-Adenosyl-L-methionine might be helpful for osteoarthritis came from studies of S-Adenosyl-L-methionine for depression. Some of the participants in the depression studies who also had osteoarthritis said their joint symptoms improved when they took S-Adenosyl-L-methionine.
Safety and Side Effects
Information on the long-term safety of S-Adenosyl-L-methionine is limited because the participants in most studies took it only for short periods of time. However, in one study of alcohol-related liver disease, participants took S-Adenosyl-L-methionine for 2 years; in that study, no serious side effects were reported.
People with bipolar disorder (an illness characterized by mood swings, from depression to mania) should not take SAMe for their depressive symptoms except under the supervision of a health care provider because SAMe may worsen symptoms of mania.
Although S-Adenosyl-L-methionine has been used to treat cholestasis during pregnancy, its safety during pregnancy has not been established.
SAMe may decrease the effects of levodopa (L-dopa), a drug used to treat Parkinson’s disease. It’s also possible that SAMe might interact with drugs and dietary supplements that increase levels of serotonin (a chemical produced by nerve cells), such as antidepressants, L-tryptophan, and St. John’s wort.
There’s a theoretical concern about the use of SAMe by people who are immunocompromised (such as those who are HIV-positive). Immunocompromised people are at risk for Pneumocystis carinii infection, and SAMe enhances the growth of this microorganism.
Side effects of SAMe are uncommon, and when they do occur they are usually minor problems such as nausea or digestive upsets.
Originator
Donamet ,Ravizza
Occurrence
SAM-e is found in all living cells and is a precursor in some amino acids.
Uses
white powder LOD 0.2%
Manufacturing Process
S-Adenosyl methionine (SAM) is produced is prepared by cultivating of
Saccharomyces cerevisiae.
One loopful of each of the microorganism strains (IFO 2342, IFO 2343, IFO
2345, IFO 2346, IFO 2347) was inoculated in 10 ml of a heat-sterilized culture
medium adjusted to pH 6.0 and composed of 5.0 g/dl of glucose, 0.5 g/dl of
polypeptone, 0.4 g/dl of KH2PO4, 0.4 g/dl of K2HPO4, 0.02 g/dl of
MgSO4·7H2O and 0.2 g/dl of yeast extract, and cultivated with shaking at
28°C for 24 h.
1 L of a culture medium adjusted to pH 6.0 and composed of 10.0 g/dl of
sucrose, 1.0 g/dl of yeast extract, 0.4 g/dl of K2HPO4, 0.01 g/dl of
MgSO4·7H2O, 1.5 g/dl of urea (separately sterilized), 0.75 g/dl of Lmethionine,
0.02 g/dl of CaCl2·2H2O, 0.25 mg/dl of ZnSO4·7H2O, 0.25 mg/dl
of FeSO4·7H2O, 125.0 mg/dl of MnSO4·6H2O, 2.0 μg/dl of CuSO4·5H2O, 2.0
μg/dl of H3BO3, 0.2 μg/dl of CoCl2·6H2O and 1.0 μg/dl of KI was put in a 2-
liter fermentor and sterilized. Then, 5 ml of the seed culture broth prepared
as above was inoculated in the culture medium and cultivated at 28°C for 72
h with aeration and agitation.
After the cultivation, the microbial cells were collected by centrifugal
separation, washed once with physiological saline, suspended in 100 ml of 1.5
N perchloric acid, and shaken at room temperature for 1 h. The suspension
was then centrifuged to remove the microbial cells, and the resulting liquid
was adjusted to pH 4.5 by adding potassium hydrogen carbonate. The
resulting precipitate of potassium perchlorate was removed by centrifugal
separation to give an extract containing SAM. The amount of SAM in the
extract was determined, and the amount of SAM based on the dry cells.The extract in an amount of 0.2 g as SAM was passed through a column filled
with 50 ml of Amberlite IRC-50 (H+ form), a weakly acidic cation exchange
resin, to cause adsorption of SAM. 0.005 N acetic acid was passed through the
column to wash it until the absorbance at 260 nm of the eluate becames less
than 0.1. Thus, impurities were removed. Then, 0.1 N sulfuric acid was
passed through the column, and SAM was eluted until the absorbance at 260
nm of the eluate becames less than 0.05. The eluate was treated with
Amberlite IRA 900 resin (OH- form) to adjust its pH to 3.0, and then
lyophilized to obtain SAM sulfate. The SAM based may be produced from SAM
sulfate by treatment with potassium hydrogen carbonate. The purity of SAM
was measured by cellulose thin-layer chromatography, paper chromatography
and high-performance liquid chromatography. The yield of SAM based on the
dry cells: IFO 2343-12.1%; IFO 2346-18.8%; IFO 2347-16.7%.
Therapeutic Function
Metabolic, Antiinflammatory
Check Digit Verification of cas no
The CAS Registry Mumber 29908-03-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,9,0 and 8 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 29908-03:
(7*2)+(6*9)+(5*9)+(4*0)+(3*8)+(2*0)+(1*3)=140
140 % 10 = 0
So 29908-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7?,8-,10-,11-,14-,27?/m1/s1
29908-03-0Relevant articles and documents
Thermostable enzyme-immobilized magnetic responsive Ni-based metal-organic framework nanorods as recyclable biocatalysts for efficient biosynthesis of: S -adenosylmethionine
He, Jie,Sun, Shanshan,Zhou, Zhao,Yuan, Qipeng,Liu, Yanhui,Liang, Hao
supporting information, p. 2077 - 2085 (2019/02/12)
A novel magnetic responsive Ni-based metal-organic framework material was developed to efficiently separate and immobilize thermal enzymes with high catalytic performance. Ni-based metal-organic framework nanorods (Fe3O4/Ni-BTC) with high magnetic responsiveness are prepared conveniently by a one-pot hydrothermal process. With the characterization, it was confirmed that Ni-based metal-organic framework nanocomposites were synthesized as nanorods mounted with magnetic Fe3O4 nanoparticles on the surface. Although Fe3O4/Ni-BTC showed a preference for histidine-tagged enhanced green fluorescent protein (His-eGFP), we found that a variety of forces played roles in enzyme immobilization, including affinity between Ni2+ and histidine tags, electrostatic attraction, hydrogen bonding and hydrophobic forces. After understanding the mechanism of the as-prepared nanocomposites, a new immobilization strategy for thermostable S-adenosylmethionine synthetase (SAMS) was further evaluated. As a result, SAMS from cell lysate achieved about 95% activity recovery in the biosynthesis of S-adenosylmethionine (SAM) under high temperature conditions (70 °C) with a simple mixing step. At the same time, the immobilized enzyme was more stable against temperature variation (by nearly 8-fold in an 80 °C water bath after 2 h) and extreme pH (by nearly 1.3-fold at pH 3) and exhibited excellent reusability after immobilization. This work indicates that magnetic responsive Ni-based nanorods are highly promising for thermostable enzyme immobilization with high efficiency and stability.
Facile chemoenzymatic strategies for the synthesis and utilization of S-adenosyl-L-methionine analogues
Singh, Shanteri,Zhang, Jianjun,Huber, Tyler D.,Sunkara, Manjula,Hurley, Katherine,Goff, Randal D.,Wang, Guojun,Zhang, Wen,Liu, Chunming,Rohr, Juergen,Van Lanen, Steven G.,Morris, Andrew J.,Thorson, Jon S.
supporting information, p. 3965 - 3969 (2014/05/06)
A chemoenzymatic platform for the synthesis of S-adenosyl-L-methionine (SAM) analogues compatible with downstream SAM-utilizing enzymes is reported. Forty-four non-native S/Se-alkylated Met analogues were synthesized and applied to probing the substrate specificity of five diverse methionine adenosyltransferases (MATs). Human MAT II was among the most permissive of the MATs analyzed and enabled the chemoenzymatic synthesis of 29 non-native SAM analogues. As a proof of concept for the feasibility of natural product alkylrandomization , a small set of differentially-alkylated indolocarbazole analogues was generated by using a coupled hMAT2-RebM system (RebM is the sugar C4′-O-methyltransferase that is involved in rebeccamycin biosynthesis). The ability to couple SAM synthesis and utilization in a single vessel circumvents issues associated with the rapid decomposition of SAM analogues and thereby opens the door for the further interrogation of a wide range of SAM utilizing enzymes. Mix and MATch: Methionine adenosyltransferase (MAT) was used to synthesize S-adenosylmethionine (SAM) analogues in a method directly compatible with downstream SAM-utilizing enzymes. As a proof of concept for the feasibility of natural product alkylrandomization by using this method, a coupled strategy in which MAT was applied in conjunction with the methyltransferase RebM was used to generate a small set of indolocarbazole analogues.
Combinations of tyrosine, methylating agents, phospholipids, fatty acids, and St. John's Wort for the treatment of mental disturbances
-
, (2008/06/13)
This invention provides therapeutic compositions for the treatment or prevention of mental disturbances such as depressive states and for regulating the level of certain neurotransmitters and thereby improving the function of the central nervous system and cognitive function in humans and other animals. The therapeutic compositions comprise any two or more of tyrosine, one or more methylating agents, one or more phospholipids, one or more fatty acids and St. John's Wort (Hypericum perforatum), whether naturally, synthetically, or semi-synthetically derived. The invention also provides a method of administering these compositions to humans or animals in need thereof.
