All Photos(1)
Synonym(s):
5′-[(3-Aminopropyl)thio]-5′-deoxyadenosine, S-Adenosyl-3-thiopropylamine, dc-SAH, dcAdoHcy, decarboxylated S-Adenosyl-L-homocysteine
Empirical Formula (Hill Notation):
C13H20N6O3S
CAS Number:
Molecular Weight:
340.40
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
Quality Level
Assay
≥98.0% (HPLC)
form
powder
storage temp.
2-8°C
SMILES string
NCCCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23
InChI
1S/C13H20N6O3S/c14-2-1-3-23-4-7-9(20)10(21)13(22-7)19-6-18-8-11(15)16-5-17-12(8)19/h5-7,9-10,13,20-21H,1-4,14H2,(H2,15,16,17)/t7-,9-,10-,13-/m1/s1
InChI key
FUSRAALGPJJIRO-QYVSTXNMSA-N
Application
S-(5′-Adenosyl)-3-thiopropylamine has been used as a calibrant solution to spike human urine samples for solid-phase extraction studies. It has also been used as an analyte in capillary electrophoresis (CE) and micellar electrokinetic chromatography (MEKC).
Biochem/physiol Actions
S-(5′-Adenosyl)-3-thiopropylamine or S-adenosyl-L-homocysteine comprises base, sugar or amino acid. It acts as an inhibitor for spermidine synthase and spermine synthase.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
This decarboxylated S-Adenosyl-L-methionine is an important metabolite in polyamine biosynthesis, acting as aminopropyl group donor for propylamine transferases such as spermine synthase and spermidine synthase.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 2 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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’.
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Jolita Sečkutė et al.
Protein science : a publication of the Protein Society, 20(11), 1836-1844 (2011-09-08)
Aminopropyltransferases are essential enzymes that form polyamines in eukaryotic and most prokaryotic cells. Spermidine synthase (SpdS) is one of the most well-studied enzymes in this biosynthetic pathway. The enzyme uses decarboxylated S-adenosylmethionine and a short-chain polyamine (putrescine) to make a
Purification of spermidine synthase from rat ventral prostate by affinity chromatography on immobilized S-adenosyl(5')-3-thiopropylamine.
K Samejima et al.
Archives of biochemistry and biophysics, 216(1), 213-222 (1982-06-01)
Alexander Vladimirovich Ivanov et al.
Electrophoresis, 41(3-4), 209-214 (2019-11-30)
A new approach for direct determination of S-adenosylmethionine (SAM), S-adenosylhomocysteine (SAH), and methylthioadenosine (MTA) in urine was developed based on MEKC by using SDS modified with isobutanol in the presence of PEG-300. Analytes were first extracted with grafted phenylborononic acid.
H Hibasami et al.
The Biochemical journal, 187(2), 419-428 (1980-05-01)
1. S-Adenosyl-l-methionine, S-adenosyl-l-homocysteine, 5'-methylthioadenosine and a number of analogues having changes in the base, sugar or amino acid portions of the molecule were tested as potential inhibitors of spermidine synthase and spermine synthase from rat ventral prostate. 2. S-Adenosyl-l-methionine was
Isolation of S-adenosyl-3-thiopropylamine.
S Ito
Methods in enzymology, 94, 463-464 (1983-01-01)
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