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43713

Sigma-Aldrich

S-(5′-Adenosyl)-3-thiopropylamine

≥98.0% (HPLC), powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C13H20N6O3S
Número de CAS:
53186-57-5
Peso molecular:
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

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «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)
Isolation of S-adenosyl-3-thiopropylamine.
S Ito
Methods in enzymology, 94, 463-464 (1983-01-01)
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
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