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5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE

CAS No.
979-92-0
Chemical Name:
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
Synonyms
S-ADENOSYL-L-HOMOCYSTEINE;s-adenosylhomocysteine;ADOHCY;hpce;Adenosylhomocysteine;S-Adenosyl-L-homocystein;S-(5'-ADENOSYL)-L-HOMOCYSTEINE;5'-DEOXY-S-ADENOSYL-;Adenosyl-L-homocysteine;L-S-AdenosylhoMocysteine
CBNumber:
CB4451354
Molecular Formula:
C14H20N6O5S
Molecular Weight:
384.41
MDL Number:
MFCD00037388
MOL File:
979-92-0.mol
Last updated:2023-05-18 11:31:00

5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Properties

Melting point 209-211 °C
Boiling point 787.5±70.0 °C(Predicted)
Density 1.91±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility 1 M HCl: soluble19.60 - 20.40mg/mL, clear to slightly hazy, colorless to faintly yellow
form crystalline
pka 2.22±0.10(Predicted)
color Off-White to Brown
BRN 99188
Stability Hygroscopic
InChIKey ZJUKTBDSGOFHSH-WFMPWKQPSA-N
FDA UNII 8K31Q2S66S

SAFETY

Risk and Safety Statements

WGK Germany  3
8-10-23
HS Code  2934990002

5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A9384 S-(5′-Adenosyl)-L-homocysteine crystalline 979-92-0 10mg $106 2024-03-01 Buy
Sigma-Aldrich 1012112 S-(5′-Adenosyl)-L-homocysteine United States Pharmacopeia (USP) Reference Standard 979-92-0 50mg $436 2024-03-01 Buy
Cayman Chemical 13603 S-Adenosylhomocysteine ≥98% 979-92-0 5mg $37 2024-03-01 Buy
Cayman Chemical 13603 S-Adenosylhomocysteine ≥98% 979-92-0 10mg $62 2024-03-01 Buy
Sigma-Aldrich A9384 S-(5′-Adenosyl)-L-homocysteine crystalline 979-92-0 25mg $179 2024-03-01 Buy
Product number Packaging Price Buy
A9384 10mg $106 Buy
1012112 50mg $436 Buy
13603 5mg $37 Buy
13603 10mg $62 Buy
A9384 25mg $179 Buy

5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Chemical Properties,Uses,Production

Description

S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative and an intermediate, by-product, or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It is also a product of S-adenosyl-methionine (SAM)-dependent methylation of biological molecules, including DNA, RNA, and histones and other proteins. SAH is a risk factor for many diseases, including cancer and neurodegenerative diseases. In addition, inhibitors that block its hydrolysis are being developed as anti-viral, anti-parasitic, anti-arthritic and immunosuppressive agents.

Chemical Properties

Pale Beige Solid

Uses

A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder.

Uses

SAH is suitable for use:

  • to investigate whether AdoHcy competes with AdoMet in the down-regulation of reporter activity of LUC reporter gene
  • as a reagent to study the abundance patterns of SAH and its correlation with vertebrate metamorphosis
  • in the optimization of the protein (lysine K) methyltransferase SET7/9 activity assay
  • in the fluorescence polarization (FP) assay during dengue virus methyltransferase activity measurement
  • as a standard for the measurement of SAH from blood samples by high performance liquid chromatography (HPLC) with fluorimetric detection method

Definition

ChEBI: The S-adenosyl derivative of L-homocysteine.

Biochem/physiol Actions

S-(5′-Adenosyl)-L-homocysteine (AdoHcy/SAH) is a component of intracellular homocysteine stress. AdoHcy is a competitive inhibitor (versus AdoMet) of DNA methyltransferases (S-adenosyl-L-methionine (AdoMet)-dependent methyltransferases) involved in epigenetics. Consequently, AdoHcy is used in a variety of studies on epigenetics in hyperhomocysteinemic states. AdoHcy is metabolized by S-adenosylhomocysteine hydrolase (AHCY). AdoHcy is the product of enzymatic transmethylation reactions involving S-Adenosylmethionine (SAM). It is reconverted to SAM by its cleavage into adenosine and L-homocysteine, a substrate of thetin-homocysteine S-methyltransferase. The concentration alterations of SAM and SAH in plasma serve as predictors of cellular methylation potential and metabolic alterations. Methylation capacity indicates specific genetic polymorphisms and/or nutritional deficiencies. Methylation is important in epigenetics, reprogramming, and cancer.

Purification Methods

It has been recrystallised several times from aqueous EtOH or H2O to give small prisms and has max 260nm in H2O. The picrate has m 170o(dec) from H2O. [Baddiley & Jameison J Chem Soc 1085 1955, de la Haba & Cantoni J Biol Chem 234 603 1959, Borchardt et al. J Org Chem 41 565 1976, NMR: Follmann et al. Eur J Biochem 47 187 1974, Beilstein 26 III/IV 3676.]

892-48-8
979-92-0
Synthesis of 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE from 5'-CHLORO-5'-DEOXYADENOSINE
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View Lastest Price from 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE pictures 2023-12-04 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
979-92-0
US $0.00-0.00 / kg 0.1kg 98% 100kg Huida Pharmaceutical Technology (Shanghai) Co., Ltd.
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE pictures 2022-10-11 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
979-92-0
US $60.00 / kg 1kg 99% 100 tons Hebei Duling International Trade Co. LTD
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE pictures 2020-03-05 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
979-92-0
US $1.00 / KG 1KG 98% HPLC 10 tons Career Henan Chemical Co

5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE Spectrum

(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methylsulfanyl]butanoic acid 5μ-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5μ-Deoxyadenosine-5μ)-L-homocysteine 5-S'-[(S)-3-Amino-3-carboxypropyl]-5'-thioadenosine Adenosyl-L-homocysteine S-(5′-Adenosyl)-L-homocysteine,5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine S-Adenosyl-L-Homocysteine (50 mg) L-5'-S-(3-AMino-3-carboxypropyl)- 5'-thioadenosine L-S-AdenosylhoMocysteine S-(5'-Deoxyadenosin-5'-yl)-L-hoMocysteine AdenosylhoMocysteine-13C5 Adenosyl-L-hoMocysteine-13C5 L-5'-S-(3-AMino-3-carboxypropyl)- 5'-thioadenosine-13C5 L-S-AdenosylhoMocysteine-13C5 S-(5'-Deoxyadenosin-5'-yl)-L-hoMocysteine-13C5 ( 35 ) -5-( 3-AMINO.-3 CARBOXYPROPYL) THIO ) -5-DEOXYADENOSINE S-ADENOSYL-L-HOMOCYSTEINE (ADENOSINE-13C10, 98%) 5'-DEOXY-S-ADENOSYL- -Adenosyl)-L-homocysteine S-(5'-deoxyadenosin-5'-yl) S-(5'-DEOXYADENOSINE-5')-L-HOMOCYSTEINE HOMOCYSTEINE, S-ADENOSYL 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE (S)-5'-(S)-(3-amino-3-carboxypropyl)-5'-thioadenosine S-(5'-Adenosyl)-L-homocysteine dihydrate Ademetionine 1,4-Butanedisulfonate Impurity 1 SAH (S-Adenosylhomocysteine) L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)- (S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid 5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE USP/EP/BP S-(5-Adenosyl)-L-Homocysteine extrapure, 99% Adenosylhomocysteine S-(5'-ADENOSYL)-L-HOMOCYSTEINE S-ADENOSYL-L-HOMOCYSTEINE s-adenosylhomocysteine ADOHCY hpce S-Adenosyl-L-homocystein S-(5'-Adenosyl)-L-homocysteine;AdoHcy;S-(5'-Deoxyadenosine)-L-homocysteine S-(5'-Deoxyadenosine)-L-homocysteine S-Adenosyl-L-Homecysteine inhibit,SAH,Endogenous Metabolite,Inhibitor Butanedisulfonate Ademetionine Impurity (S)-2-Amino-4-[[[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-2-tetrahydrofuryl]methyl]thio]butanoic Acid 5'-Deoxy-S-Adenosyl-L-Homocystmine 979-92-0 972-92-0 C14H20N6O5S C14H20N6O5S2H2O A - H BioChemical Amino Acid Library Amino Acids and Peptides Biochemicals and Reagents Metabolic Libraries Metabolomics Modified Amino Acids amino acids Amino Acids & Derivatives