Merck
CN
All Photos(4)

Documents

A7007

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride

≥75%

Sign Into View Organizational & Contract Pricing
All Photos(4)
Synonym(s):
SAM, Active methionine, AdoMet, SAM chloride dihydrochloride
Empirical Formula (Hill Notation):
C15H23ClN6O5S · 2 HCl
CAS Number:
86867-01-8
Molecular Weight:
507.82
Beilstein:
6560002
MDL number:
MFCD22571809
PubChem Substance ID:
24891164
NACRES:
NA.32

Quality Level

300

Assay

≥75%

form

powder

color

white to off-white

solubility

H2O: 100 mg/mL

application(s)

cell analysis

shipped in

dry ice

storage temp.

−20°C

SMILES string

Cl.Cl.[Cl-].C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23

InChI

1S/C15H22N6O5S.3ClH/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);3*1H/t7-,8+,10+,11+,14+,27?;;;/m0.../s1

InChI key

KBAFOJZCBYWKPU-XQVUROGGSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride (SAM) facilitates the transfer of methyl groups to proteins, lipids and nucleic acids. Methionine adenosyl transferase catalyses the synthesis of SAM from methionine and adenosine triphosphate (ATP). SAM functions to regulate various cellular functions like cell division, cell death, transcription, genetic stability, oxidant/antioxidant balance and polyamine homeostasis. Therapeutically, SAM finds its application as a nutritional supplement in humans for various diseases like osteoarthritis and liver injury. SAM also regulates transsulfuration reactions by binding to the regulatory domain of key enzyme cystathionine-β-synthase (CBS).

Application

S-(5′-Adenosyl)-L-methionine chloride dihydrochloride has been used as a medium supplement for S30 cell extract. It also has been used for measuring the interaction with catechol-O-methyltransferase (COMT) by quartz crystal microbalance (QCM), surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) with supported lipid bilayers and vesicles.

Biochem/physiol Actions

Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.

Caution

This material is 80-90% pure when prepared, but is very unstable. As much as 10% purity loss per day at 25 °C has been noted.

Analysis Note

Purity based on UV and HPLC.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Ted M Lakowski et al.
Analytical biochemistry, 396(1), 158-160 (2009-09-08)
S-Adenosyl-L-homocysteine (AdoHcy) background signal in reactions with protein arginine N-methyltransferase 1 is investigated using an ultrahigh-performance liquid chromatography tandem mass spectrometry assay that measures AdoHcy. We identify three sources of AdoHcy background: enzymatic automethylation, AdoHcy contamination in commercial S-adenosyl-L-methionine (AdoMet)
Yan Zhang et al.
Archives of microbiology, 191(10), 773-783 (2009-09-05)
Enolase-phosphatase (E1), as an enzyme, is involved in methionine salvage pathway in many prokaryotic and eukaryotic organisms. But the identity and function of E1 in Xanthomonas oryzae pv. oryzae (Xoo) remain undetermined. Here, we report the cloning and characterization of
Chemical communication between bacteria and cell-free gene expression systems within linear chains of emulsion droplets
Schwarz-Schilling M, et al.
Integrative Biology : Quantitative Biosciences from Nano to Macro, 8(4), 564-570 (2016)
Andria V Rodrigues et al.
Chembiochem : a European journal of chemical biology, 21(5), 663-671 (2019-09-13)
We recently reported the discovery of phenylacetate decarboxylase (PhdB), representing one of only ten glycyl-radical-enzyme reaction types known, and a promising biotechnological tool for first-time biochemical synthesis of toluene from renewable resources. Here, we used experimental and computational data to
Membrane bound COMT isoform is an interfacial enzyme: general mechanism and new drug design paradigm
Magarkar A, et al.
Chemical Communications (Cambridge, England), 54(28), 3440-3443 (2018)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service