SAMe-1,4-Butanedisulfonate-d , CAS No.S1437905

CAS: S1437905 Cat. No.: S1437905 Formule: C₁₅H₂₃D₃N₆O₅S.C₄H₁₀O₆S₂.₁/₂C₄H₈O₆S₂ Poids moléculaire: 728.14

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

SAMe-1,4-Butanedisulfonate -d 3 is the deuterium labeled SAMe-1,4-Butanedisulfonate. SAMe-1,4-Butanedisulfonate , a natural compound, is a methyl donor in the central nervous system. SAMe-1,4-Butanedisulfonate has antidepressant activity. SAMe-1,4-Butanedisulfonate can be used for research of CNS disorders

Specifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Poids moléculaire

728.14

Application Protocols

No item-specific validated protocols are provided. Below are general, literature-based examples for using deuterium-labeled SAMe in research.

A) General methyltransferase assay (LC–MS readout):

• Prepare buffer (e.g., 50 mM HEPES pH 7.5, 50 mM NaCl, 1 mM DTT). Chill on ice.
• Dissolve SAMe-1,4-butanedisulfonate-d freshly in cold buffer to the desired working concentration. Keep on ice; protect from light.
• Mix enzyme, substrate, and SAMe. Incubate at 25–30°C for 30–60 min (optimize per enzyme).
• Quench with equal volume of cold 0.1% formic acid in water/ACN (1:1). Clarify by centrifugation.
• Analyze by LC–MS/MS, extracting ion chromatograms for unlabeled and mass-shifted product. Quantify methylation extent using internal standards.

B) Metabolomics tracer incorporation (cell-free lysate):

• Prepare lysate in volatile buffer (e.g., 50 mM ammonium formate, pH 6.5) containing EDTA and a mild reductant if compatible.
• Spike with SAMe-1,4-butanedisulfonate-d at the target tracer level.
• Incubate at 37°C for defined time; rapidly quench metabolism with cold methanol/water (80:20) containing 0.1% formic acid.
• Clarify and analyze SAH, methylated metabolites, and residual SAMe by LC–MS.

Note: Optimize concentrations, pH, and temperature for your enzyme/system. Verify isotopic label position/enrichment on the CoA to interpret mass spectra.

Biological Roles

General/literature context (informational; not product specifications):

• Central methyl donor: S-Adenosyl-L-methionine (SAM) is synthesized in cells from methionine and ATP by methionine adenosyltransferase. It serves as the principal methyl group donor for methyltransferases acting on DNA, RNA, proteins, lipids, and small molecules.
• One-carbon metabolism: SAM lies at the nexus of the methionine and folate cycles. After methyl donation, S-adenosylhomocysteine (SAH) is formed, which is hydrolyzed to adenosine and homocysteine. Intracellular SAM/SAH ratios regulate methylation potential.
• Polyamine and radical chemistry: SAM participates in decarboxylated SAM-dependent aminopropyl transfers during polyamine biosynthesis and in radical SAM enzyme reactions that generate 5′-deoxyadenosyl radicals (separate enzyme class, not the same cofactor pool used for methyl donation).
• Isotope tracers: Deuterium-labeled SAM variants enable tracking methyl flux and methylation stoichiometry by mass spectrometry, discerning enzymatic vs non-enzymatic processes and enabling kinetic isotope effect studies when labeling is at the transferable methyl (exact labeling for this item is not specified).

Application note: When used in cell-free systems or lysates, include SAH hydrolase or scavengers or design reaction conditions to mitigate SAH product inhibition, a key regulator in methyltransferase assays.

Buffer Applications

Applicability: Highly relevant. SAMe salts are commonly used in buffered aqueous systems for enzymology and analytical workflows.

General/literature guidance (informational):

• pH range: Maintain mildly acidic to near-neutral conditions (typ. pH 5.5–7.5) balancing enzyme requirements with SAMe stability. Many methyltransferases operate well in pH 7–8; stability considerations may favor the low end of the enzyme’s pH range.
• Common buffer systems: MES (pH 5.5–6.7), HEPES (pH 6.8–8.2), MOPS (pH 6.5–7.9), or phosphate (pH 6–7.5). For LC–MS workflows, use volatile systems (ammonium formate/acetate with formic/acetic acid).
• Additives: 0.5–2 mM EDTA to chelate adventitious metals; 0.5–5 mM DTT or TCEP when compatible to limit oxidative degradation; 0.01–0.05% Tween-20/BSA for adsorption control in low-protein assays (test compatibility).
• Ionic strength: 50–200 mM NaCl or KCl often improves enzyme stability. Mg2+ may be needed for certain enzymes or substrates.
• Preparation: Dissolve SAMe immediately before use in cold buffer; filter-sterilize if required. Keep solutions on ice and shielded from light. Confirm concentration spectroscopically at 260 nm using literature extinction coefficients, adjusting for salt form.

Note: The exact buffer and pH should be optimized per enzyme/substrate system. Consult the item’s CoA for any stabilizer content or recommended diluents if provided.

Green Alternatives

Context: As an aqueous, ionic biochemical reagent, SAMe-1,4-butanedisulfonate-d is typically used in water-based buffers. Classical solvent substitution guidance is therefore less central than for organic reagents.

Greener practice considerations (general):

• Solvent system: Favor water and volatile, low-toxicity buffer components (e.g., ammonium formate/acetate with formic/acetic acid) for LC–MS compatibility and greener profiles vs non-volatile phosphate where possible.
• Temperature/energy: Minimize thermal stress by conducting assays at ambient to 37°C only as required by enzyme kinetics; avoid unnecessary heating/cooling cycles to reduce energy consumption while balancing SAMe stability needs.
• Packaging and waste: Use minimal volumes; scale experiments to reduce aqueous waste. Neutral aqueous waste streams containing organosulfonates are generally low hazard; confirm via SDS and local regulations.
• Cold-chain optimization: Shipments on ice are specified for this item. Upon receipt, promptly transfer to -20°C to shorten the time on ice and minimize dry ice/ice-pack use in subsequent shipments.

Comparison (qualitative):

• SAMe disulfonate vs organic methylating agents (e.g., MeI, Me2SO4): Enzymatic methylation with SAMe provides selectivity and operates in water at mild pH, avoiding toxic/volatile alkylating agents. Trade-off: Requires compatible enzymes and is not a direct substitute for non-enzymatic methylations.

Note: These are general sustainability practices; adapt to your workflow and institutional EHS guidance.

Pharmaceutical Uses

This product is supplied for research use only. No clinical, diagnostic, or therapeutic uses are claimed or supported for this item.

General context (informational):

• SAMe and its salts have been studied and formulated in various non-clinical research contexts; however, pharmaceutical-grade specifications, GMP manufacturing status, residual solvent limits, and compendial compliance (e.g., USP/EP) are not provided for this item.
• Excipients/processing aids: 1,4-butanedisulfonate acts as a counterion for improved aqueous solubility in research settings. Its suitability as an excipient in regulated products would require separate safety and quality evaluation.

For any formulation or translational work, obtain appropriate GMP-grade materials and follow regulatory guidance. Use this catalog item only in research laboratory experiments.

Physical Properties

Item-specific physical constants:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• pKa/logP/refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for SAMe disulfonate salts (informational, not specifications):

• Physical form: Typically isolated as a hygroscopic, highly polar solid; often supplied as a stable salt with di- or polysulfonate anions to improve handling in air and to increase water solubility.
• Solubility (literature, qualitative): Freely soluble in water and aqueous buffers; negligible solubility in nonpolar organic solvents. Aqueous stability is favored at mildly acidic pH (ca. pH 3–6); decomposition accelerates under neutral to basic conditions due to sulfonium demethylation or hydrolysis.
• Thermal behavior: SAM salts are heat-sensitive; prolonged warming promotes decomposition (literature). Cold-chain handling is customary.
• UV characteristics: Adenosyl chromophore gives strong absorbance near 259–260 nm (literature), useful for HPLC/UV monitoring. Extinction coefficients depend on salt form and pH; consult literature or CoA.

Note: Use the item’s CoA/Spec Sheet for definitive values when planning quantitative work or method validation.

Quality and Grades

Item-specific quality data:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance (general):

• Research grade: For most biochemical reagents like SAMe salts, “research grade” typically indicates suitability for laboratory applications without certification for clinical or diagnostic use. Purity is commonly reported by HPLC or NMR; residual moisture and counterion stoichiometry can influence apparent purity.
• Counterion content: For polyanionic salts (e.g., 1,4-butanedisulfonate), exact stoichiometry and water of hydration can vary. The CoA should state the salt ratio, assay basis (free base equivalent or as-is), and any residual solvent.
• Stabilizers: Some SAMe salts are offered with acid stabilizers or as lyophilized solids to improve shelf life. For this item, stabilizers are not specified; refer to CoA/Spec Sheet.
• Identity testing: Vendors commonly verify identity via 1H/13C NMR, MS, and HPLC purity. For isotopologues, isotope enrichment (%D) and labeling position(s) should be reported; confirm on the CoA.
• Functional assays: For methyltransferase applications, suppliers may report activity retention after storage under specified conditions. This item does not list such data; validate in-house as needed.

Recommendation: Use the product’s CoA for exact purity, isotopic enrichment, salt stoichiometry, and analytical methods before method validation or quantitative studies.

Reaction and Applications

Manufacturer Applications: Not specified in Product Data. The following expands on typical research uses of SAMe isotopologues (general literature context).

Biochemical/analytical applications:

• Methyltransferase cofactor: SAMe is the universal methyl donor in enzymatic methylation of DNA, RNA, proteins, and small molecules. Deuterium-labeled SAMe enables tracing of methyl incorporation by MS via characteristic mass shifts (e.g., +n Da in products, where n equals the number of deuterons at the transferable methyl position if so labeled; exact labeling for this item not specified).
• Metabolomics and flux analysis: Employed as an internal standard or tracer to monitor one-carbon metabolism, methionine cycle dynamics, and transmethylation rates.
• Enzyme kinetics: Determine Km, kcat, and inhibitor mechanisms for DNA/RNA methyltransferases (DNMTs, RNMTs), protein methyltransferases (PRMTs, PKMTs), and small-molecule O/N/S-methyltransferases.

Practical considerations:

• Solution prep: Use freshly prepared, acidified aqueous buffer; keep on ice. Avoid repeated freeze–thaw.
• Detection: LC–MS/MS or LC–UV at ~260 nm for cofactor; mass-shifted product ions for labeled methyl transfer. Consider isotope effects on retention and fragmentation.
• Controls: Include no-enzyme and no-cofactor controls to assess non-enzymatic background. Confirm the position/extent of deuterium labeling from the CoA to correctly interpret mass deltas.

Note: For non-enzymatic synthetic methylations, SAMe is rarely used; its utility is primarily in enzymology and bioanalytical workflows.

Reaction Conditions

Item-specific conditions are not provided. The following are general, literature-based guidelines for SAMe-dependent reactions and analyses; adapt to your enzyme/substrate system.

Typical enzymatic methylation conditions (examples):

• DNA methyltransferase (DNMT) assays: 10–100 nM enzyme; 100–500 nM DNA substrate; SAMe in the low to mid micromolar range; buffer pH 7.4 (HEPES or Tris), 1–5 mM MgCl2, 50–150 mM NaCl, 0.5–1 mM DTT; 25–37°C; 15–120 min. Monitor product by restriction protection, radiometric displacement, or LC–MS for isotopic incorporation (literature ranges).
• Protein methyltransferase (PRMT/PKMT) assays: 0.1–2 µM enzyme; peptide/protein substrate 1–50 µM; SAMe 5–100 µM; pH 7.5 HEPES, 0.01% Tween-20, 1 mM TCEP; 25–30°C; 30–90 min. Analyze by LC–MS/MS or antibody-based detection where appropriate (literature ranges).
• Small-molecule O/N/S-methyltransferases: Conditions similar to above, with Mg2+ or other cofactors as enzyme-dependent.

Analytical conditions:

• HPLC: Reverse-phase C18 with aqueous acidic mobile phase (e.g., 0.1% formic acid) and modest organic (5–10% MeOH/ACN); detect SAMe at ~260 nm. LC–MS/MS for sensitivity and isotope resolution.

Notes:

• Confirm the isotopic labeling position and enrichment for this item on the CoA to interpret mass shifts correctly.
• Maintain solutions cold and slightly acidic where compatible to limit cofactor degradation.

Safety and Handling

Item-specific hazard information:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification and Pictograms: Not specified for this item; refer to SDS.

General safety guidance (informational; defer to SDS for authoritative instructions):

• Expected hazards: SAMe disulfonate salts are non-volatile, strongly water-soluble solids. They are not typically flammable but may be irritating to eyes/skin upon contact (general). Avoid inhalation of dusts and ingestion.
• PPE: Laboratory coat, safety glasses, and appropriate chemical-resistant gloves. Use in a clean, dry environment; handle powders in a fume hood or ventilated balance enclosure to minimize dust.
• Incompatibilities: Avoid strong bases (accelerated SAMe decomposition), strong oxidizers/reductants that may alter the adenosyl or sulfonium moieties, and heavy metal contaminants that can catalyze degradation (general/literature).
• Stability precautions: Keep cold, dry, and protected from light. Minimize time at ambient temperature. Use acidified aqueous buffers for solutions when compatible with your application.
• First aid (overview): If on skin/eyes, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth with water. Seek medical attention as appropriate. Always consult the SDS for the product-specific response.

Waste: Dispose of aqueous solutions and contaminated materials according to institutional and local regulations for non-hazardous organic salts unless SDS specifies otherwise.

Solvent Selection

Applicability: As a highly polar ionic biomolecule salt, SAMe-1,4-butanedisulfonate-d is intended for use in aqueous systems. Organic solvent selection is typically secondary and application-dependent.

General guidance (literature/context):

• Primary medium: Water or aqueous buffers at mildly acidic pH (commonly pH 3–6) to enhance stability of the SAM sulfonium center.
• Miscibility profile: Freely miscible with water; insoluble or poorly soluble in nonpolar solvents. In mixed aqueous-organic systems, maintain sufficient water fraction (>50%) to keep SAMe in solution.
• Compatible additives: Low concentrations of salts (e.g., NaCl), Mg2+ for enzyme systems requiring cofactors, chelators (e.g., EDTA) to suppress metal-catalyzed degradation, reducing agents (e.g., DTT, TCEP) if compatible with downstream detection (literature). Verify compatibility with the isotopic label and assay chemistry.
• Incompatible conditions: Strongly basic pH, high temperatures, and high organic content (which may precipitate the salt) can lead to decomposition or loss of activity in enzymatic assays.

Comparison (general):

• SAMe disulfonate vs chloride/p-toluenesulfonate salts: Disulfonate salts often exhibit improved water solubility and handling vs less polar counterions, at the expense of higher inorganic/anion load in formulations.

Practical tip: Prepare fresh solutions immediately before use; filter through 0.22 µm if necessary. For LC–MS workflows, use volatile acidic buffers (e.g., ammonium formate/formic acid) to maintain pH and MS-compatibility.

Storage and Reconstitution

Item-specific instructions (from Product Data):

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.

General best practices (informational):

• Upon receipt: Allow the shipping container to equilibrate to room temperature before opening to avoid condensation. Immediately transfer the product to -20°C storage as specified.
• Container handling: Keep tightly closed. Protect from moisture and light. Many SAMe salts are hygroscopic and heat-sensitive (general); minimize time at ambient temperature.
• Reconstitution: Dissolve in cold, acidified aqueous buffer compatible with your application (e.g., pH 5.5–7.0). Filter-sterilize if required. Prepare fresh working solutions just before use.
• Aliquoting: If repeated use is expected, prepare single-use aliquots and refreeze at -20°C to avoid freeze–thaw cycles. Label aliquots with date and concentration.
• Stability monitoring: Track integrity by HPLC/UV (260 nm) or LC–MS where available, watching for formation of S-adenosylhomocysteine (SAH) or other breakdown products. Actual shelf life in solution depends strongly on pH and temperature.

Notes:

• Appearance, exact solvent compatibility, and any stabilizers are not specified for this item; refer to the CoA/Spec Sheet.
• For long-term storage beyond routine use, consider desiccated conditions and secondary containment to limit moisture ingress.

Structure and Identity

Overview: SAMe-1,4-Butanedisulfonate-d is described as a deuterium-labeled S-adenosyl-L-methionine (SAMe) salt paired with 1,4-butanedisulfonate counterion(s). Specific identifiers for this item are not provided in the Product Data.

Item-specific identifiers (from Product Data):

• CAS: S1437905 (catalog reference, not a standard CAS)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature context):

• Cation: S-adenosyl-L-methionine (SAM) is a sulfonium species derived from ATP and L-methionine. It contains an adenosyl nucleoside moiety, a ribose, and a sulfur-bearing methioninium center (R–S+(CH3)–). The positive charge resides on sulfur.
• Counterion: 1,4-butanedisulfonate is a dianionic sulfonate species that forms stable salts with cationic biomolecules, enhancing water solubility and solid-state stability (general property of disulfonate salts).
• Isotopic labeling: “-d” indicates a deuterium-labeled isotopologue. The exact labeling position and number of deuterons are not specified for this item; refer to CoA/Spec Sheet.
• Stereochemistry: SAM is chiral at the L-methionine center and at the ribose; typical SAMe used in biochemistry is the L-configuration (literature). Specific stereochemical confirmation for this item is not specified; refer to CoA/Spec Sheet.

2D structure (verbal, general): Adenosyl purine base linked to ribose (N9–C1′ glycosidic bond), ribose 5′ tethered via 5′-carbon to a methioninium sulfonium through the 3-carbon chain of methionine; paired with a dianionic 1,4-butanedisulfonate.

Synthetic Utility

Primary utility: Biochemical methyl donor for enzymatic transformations rather than a conventional synthetic reagent.

General/literature perspective:

• Enzymatic methylations: SAMe-dependent methyltransferases enable highly selective C-, N-, O-, and S-methylations on complex substrates under mild aqueous conditions. Deuterium-labeled SAMe variants serve as methyl donors that transfer labeled methyl groups (if labeling is at the transferable methyl; exact labeling for this item is not specified), facilitating isotopic labeling of products for mechanistic or analytical purposes.
• Chemoenzymatic synthesis: Combining SAM-dependent enzymes with chemical steps can construct site-specifically methylated natural products, nucleic acids, or proteins. Cofactor recycling systems (e.g., using methionine adenosyltransferase with ATP regeneration) can reduce SAMe consumption.
• Not typically used for: Non-enzymatic methylations common in organic synthesis (e.g., using MeI, Me2SO4, MeOTf) because SAMe is unstable under basic, non-aqueous conditions and requires enzyme catalysis for selectivity and rate.

Retrosynthetic value: In planning site-specific methyl installations, identify an appropriate methyltransferase and design a regeneration scheme for SAMe. The isotopic label in SAMe-1,4-butanedisulfonate-d enables incorporation of mass tags for downstream MS confirmation and quantitation.

Target Specificity

Not applicable. This product is a small-molecule biochemical reagent (a SAMe salt), not an antibody or affinity reagent. No antigen/epitope or species specificity applies. For enzyme studies, selectivity depends on the methyltransferase chosen in your assay rather than on the cofactor itself.

Foire aux questions

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is S1437905, the molecular formula is C15H23D3N6O5S.C4H10O6S2.1/2C4H8O6S2, and the molecular weight is 728.14 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.