Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

43713

Sigma-Aldrich

S-(5′-Adenosyl)-3-thiopropylamine

≥98.0% (HPLC), powder

Synonym(s):

5′-[(3-Aminopropyl)thio]-5′-deoxyadenosine, S-Adenosyl-3-thiopropylamine, dc-SAH, dcAdoHcy, decarboxylated S-Adenosyl-L-homocysteine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C13H20N6O3S
CAS Number:
53186-57-5
Molecular Weight:
340.40
MDL number:
MFCD17215932
UNSPSC Code:
12352204
PubChem Substance ID:
329756367
NACRES:
NA.32

product name

S-(5′-Adenosyl)-3-thiopropylamine, ≥98.0% (HPLC)

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Isolation of S-adenosyl-3-thiopropylamine.
S Ito
Methods in enzymology, 94, 463-464 (1983-01-01)
Lin Huang et al.
Nucleic acids research, 48(13), 7545-7556 (2020-06-11)
While most SAM riboswitches strongly discriminate between SAM and SAH, the SAM/SAH riboswitch responds to both ligands with similar apparent affinities. We have determined crystal structures of the SAM/SAH riboswitch bound to SAH, SAM and other variant ligands at high

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