Spaglumic acid-d , CAS No.S1439995

CAS: S1439995 Cat. No.: S1439995 Formula: C₁₁H₁₃D₃N₂O₈ Peso molecolare: 307.27

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Spaglumic acid-d 3 (N-Acetylaspartylglutamic acid-d 3 ) is the deuterium labeled Spaglumic Acid. Spaglumic Acid is a neuropeptide.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

Peso molecolare

307.27

Application Protocols

No item-specific tested applications provided in Product Data. The following protocols are general, literature-based examples for deuterated NAAG used as an internal standard.

Example 1: LC–MS/MS quantitation of NAAG (general)

• Prepare a 1–5 mM stock of spaglumic acid-d in water or 50:50 water:DMSO. Aliquot and store at −20°C.
• Spike biological samples (e.g., tissue extract, biofluid) with internal standard at a fixed concentration (e.g., 50–500 nM final) prior to protein precipitation or extraction.
• Precipitate proteins with 3–4 volumes of cold acetonitrile or ethanol; centrifuge and collect supernatant.
• LC–MS: Use HILIC or highly aqueous RP; monitor native NAAG and D-labeled analog in MRM. Construct calibration curves with matrix-matched standards.

Example 2: Enzymatic turnover assay (general)

• Incubate NAAG with GCPII-containing preparation in HEPES buffer (pH 7.4) at 37°C. Add a fixed amount of spaglumic acid-d to each reaction/quenched sample as post-extraction standard for recovery correction.
• Quench at timepoints with organic solvent or acid, clear by centrifugation, and analyze products by LC–MS.

Adjust concentrations and conditions to your instrument sensitivity and matrix; validate recovery and linearity.

Biological Roles

Literature overview (general; not product-specific and not clinical)

• Spaglumic acid (NAAG) is an abundant dipeptidic neurotransmitter/neuromodulator in mammalian nervous tissue. It is synthesized from N-acetylaspartate (NAA) and L-glutamate by NAAG synthases and hydrolyzed extracellularly by glutamate carboxypeptidases (e.g., GCPII/“NAALADase”) to yield NAA and glutamate.
• Receptor interactions: NAAG is reported to act as an agonist at group II metabotropic glutamate receptors, particularly mGluR3, modulating presynaptic neurotransmitter release (literature).
• Compartmentalization: NAAG is stored in synaptic vesicles and released in an activity-dependent manner; its extracellular lifetime is regulated by ecto-enzymatic hydrolysis.
• Biochemical relevance: Quantifying NAAG is important in studies of glutamatergic signaling, neuron–glia interactions, and metabolic coupling involving NAA.

Use of deuterated standard (general)

• Isotopically labeled NAAG enables accurate mass-spectrometric quantification across tissues and biofluids, supporting pathway analysis of synthesis and catabolism without implying any therapeutic application.

Note

• The above describes biological roles of the native molecule in research contexts; it does not imply clinical use. The present product is designated For research use only (per Product Data).

Buffer Applications

Applicability

• As a multi-acidic dipeptide-like analyte, spaglumic acid solutions are typically prepared in aqueous buffers for biochemical assays and analytical standards. It is not a classical buffering agent itself.

General guidance (literature/practice)

• Suitable buffers: Phosphate (10–50 mM), HEPES, MOPS, or ammonium acetate/formate for LC–MS compatibility. Choose pH 6.5–8.0 to balance solubility and stability of amide bonds.
• Avoid: Strong alkaline conditions (pH >9) and strong acids for prolonged periods, which can promote hydrolysis. Minimize non-volatile salts if samples are destined for MS analysis.
• Ionic strength: Moderate ionic strength (10–100 mM) can improve chromatographic peak shape for polyacids, particularly in HILIC.

Practical recipes (examples; general)

• LC–MS stock: 10 mM ammonium formate in 95:5 water:acetonitrile, pH ~6.8; prepare standard curves with matrix-matched diluents.
• Biochemical assay: 25 mM HEPES, 100 mM NaCl, pH 7.4; include divalent cations only if required by concomitant enzymes and after verifying no adverse effects on stability/adsorption.

Note

• Item-specific buffer compatibility and concentration limits are Not specified for this item; refer to CoA/Spec Sheet if available.

Green Alternatives

Context

• Spaglumic acid-d is a specialized, deuterated analytical standard. “Green alternatives” are most meaningfully considered for the solvents and workflows used with this analyte rather than replacing the analyte itself.

Greener workflow suggestions (general)

• Prefer water-based buffers over high percentages of organic solvents whenever chromatographic retention permits.
• Select volatile, lower-toxicity modifiers for LC–MS (e.g., ammonium formate/acetate at low millimolar concentrations) rather than non-volatile salts.
• Minimize DMSO volumes in stocks; promptly dilute into aqueous media to reduce solvent load and waste.
• For protein precipitation/sample cleanup, consider ethanol instead of acetonitrile where performance is acceptable, noting potential changes to recovery.

Comparison of mobile-phase modifiers (general)

• Formic acid (0.1%): widely used, volatile, MS-friendly; strong proton source but may reduce retention of very polar acids on RP.
• Ammonium acetate/formate (2–10 mM): volatile, pH control around neutral; can improve peak shape of polyacids and enable HILIC.

Waste minimization

• Use microflow LC or smaller injection volumes where sensitivity allows.
• Consolidate calibration runs and employ bracketing standards to reduce the number of injections without compromising data quality.

Pharmaceutical Uses

This listing is provided For research use only (per Product Data). No medical or clinical claims are made.

Relevant non-clinical/industry contexts (general)

• Bioanalytical standard: Deuterated spaglumic acid can serve as an internal standard for method development and validation in nonclinical DMPK and biomarker assays (e.g., LC–MS/MS quantitation in tissue homogenates or biofluids).
• Reference material: Useful for cross-laboratory comparability, instrument qualification, and stability-indicating method development for NAAG in complex matrices.
• Formulation studies (preclinical research): Can support forced-degradation studies of NAAG in candidate formulations to understand degradation pathways (hydrolysis) without implying therapeutic application.

Regulatory note (general)

• If used in GLP or regulated environments, ensure the lot-specific CoA includes isotopic enrichment, purity, counterion/form, residual solvent profile, and trace isotopologue distribution necessary for bioanalytical validation. Item-specific pharmacopeial status is Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific values (Product Data)

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

Storage/Shipping (Product Data)

• Storage: Store at -20°C.
• Shipping: Ice chest + Ice pads.

Literature/general physical characteristics (for context; not item-specific specifications)

• Aggregate state: typically obtained as a solid, often as the free acid or a sodium salt; solids of peptide-like acids often appear as white to off-white powders.
• Thermal behavior: peptide-like acids generally show broad decomposition rather than a sharp melting point; boiling point is not meaningful (decomposes before boiling).
• Solubility: highly water-soluble at neutral to basic pH due to multiple carboxylates; limited solubility in most aprotic organic solvents. Solubility may increase in aqueous buffers or with pH adjustment (literature).
• Ionization: multiple acidic groups; isoelectric point expected in the acidic range; no free primary amine (acetylated and involved in amide bond) (literature).
• Hygroscopicity: multi-acidic, polar compounds can be moisture-sensitive; handle quickly in ambient air and reseal promptly (general guidance).

If numeric values (pKa, logP, density, refractive index, water content) are required for your method validation: Not specified for this item; refer to CoA/Spec Sheet, or consult peer-reviewed literature for NAAG.

Quality and Grades

Item-specific quality information

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

How to interpret grades for this compound class (general guidance)

• Reference/Isotopic standard grade: Deuterated analytes are often provided as analytical standards for LC–MS/GC–MS quantitation. Such grades prioritize isotopic enrichment, chemical purity, and well-characterized impurity/isotope profiles.
• Research grade: Suitable for discovery and method development; may have broader tolerance on residual solvents/salts.

Key considerations for deuterated spaglumic acid

• Isotopic labeling: The exact labeling pattern (position(s) of D) and isotopic enrichment directly affect mass transitions and retention behavior. For quantitative bioanalysis, request documentation of labeling pattern and D%.
• Counterions/form: Free acid vs salt form (e.g., sodium) influence solubility and pH. Confirm form on the CoA before preparing standards.
• Trace impurities: Residual non-deuterated NAAG or partially deuterated isotopologues can contribute to isotopic cross-talk in MRM methods; CoA typically lists these as % of total.

Recommendation

• For regulated assays and high-accuracy quantitation, obtain and retain the item’s CoA/SDS and, if available, an isotopic abundance report. Where not specified above, refer to CoA/Spec Sheet for definitive specifications.

Reaction and Applications

Manufacturer applications (from catalog)

• Not specified in Product Data.

Analytical/research applications (literature/general; expand for deuterated standard)

• Internal standard for LC–MS/MS quantitation of endogenous N-acetylaspartylglutamate in brain, CSF, or cell extracts. The deuterated analog provides co-elution and compensates for matrix effects and variable recovery during sample prep.
• Calibration/QA: Preparation of calibration curves, QC samples, and isotopic-dilution assays for enzyme studies involving NAAG metabolism.
• Enzymology: Substrate/marker for glutamate carboxypeptidases (e.g., GCPII/“NAALADase”) activity assays; the D-labeled standard allows accurate turnover measurements by MS.

Practical notes (general)

• Stock solutions: Prepare in water, buffer (pH 7–8), or DMSO-water mixtures. Filter through 0.2 µm if particulate is present.
• Stability: Avoid strong acid/base and prolonged elevated temperatures. Aliquot and store at −20°C or below to limit hydrolysis of amide bonds.
• LC considerations: For reversed-phase methods, highly aqueous initial conditions or ion-pair reagents may be required; alternatively, use HILIC for robust retention.
• Derivatization: For fluorescence or GC methods, carbodiimide- or NHS-ester–mediated tagging of carboxyls can enhance detectability; verify that derivatization does not scramble isotopic label (general caution).

All application details above are general literature practices for NAAG-like analytes and deuterated internal standards.

Reaction Conditions

Not a general-purpose reagent; however, the following literature/practice notes are relevant for handling, derivatization, and analysis of NAAG-like analytes.

Typical conditions (general)

• Derivatization for detection: EDC (0.1–0.5 M) with NHS (0.1–0.2 M) in MES buffer (pH 5.0–6.0), 0–25°C for 15–60 min, to form NHS esters for subsequent tagging. Quench residual EDC/NHS before LC–MS.
• Enzymatic assays: GCPII activity commonly run in HEPES or Tris buffers (pH 7.3–7.6) at 25–37°C; monitor NAAG consumption and glutamate/NAA formation by LC–MS or fluorometric coupling. Include appropriate cofactors only if validated.
• LC–MS analysis: HILIC column; mobile phase A = 10 mM ammonium formate in water, pH ~6.8; B = acetonitrile. Gradient from high B (90–95%) to lower B over 5–10 min; ESI in negative mode frequently affords robust response for polyacids. Reversed-phase methods may require highly aqueous starts or ion-pairing (e.g., 2–5 mM HFBA), noting MS tradeoffs.

Cautions (general)

• Isotopic integrity: Avoid conditions that can promote H/D exchange at labile positions (strong base, metal-catalyzed exchange, or prolonged aqueous exposure at elevated temperature) if the labeling sites are exchangeable.
• Stability: Limit exposure to pH extremes and heat to reduce amide hydrolysis.

Safety and Handling

GHS/SDS information (Product Data)

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-phrases): Not specified for this item; refer to SDS.
• GHS classification and pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (literature/general; not product-specific)

• Expected hazards: peptide-like polyacids are generally of low acute toxicity but may cause eye/skin/respiratory irritation. Avoid inhalation of dusts and contact with eyes or mucosa.
• PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask or handle in a fume hood if aerosolization/dusting is possible.
• Handling: minimize exposure to ambient humidity; cap containers promptly. Use clean, dry tools to prevent contamination.
• Incompatibilities: strong oxidizers and bases/acids that may degrade amide bonds at extremes of pH and temperature. Avoid prolonged exposure to elevated temperatures.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with copious water for at least 15 minutes; remove contaminated clothing.
  • Ingestion: rinse mouth; seek medical attention.
• Waste: dispose according to institutional and local regulations for non-halogenated, aqueous organic waste.

Authoritative safety data reside in the product SDS. Always consult the SDS and your institutional EHS guidance before use.

Solvent Selection

Applicability

• As a highly polar, multi-acidic dipeptidic analyte, spaglumic acid (NAAG) is best handled in aqueous media. Organic solvent selection is primarily relevant for sample cleanup, LC mobile phases, and stock solution stability.

General solvent behavior (literature/general)

• Water/buffers: High solubility in water and common biological buffers, with pH-dependent ionization. Neutral to slightly basic pH typically maximizes solubility.
• Protic organics: Limited solubility in methanol/ethanol unless water is present; miscible with aqueous alcohols for LC–MS sample preparation.
• Aprotic organics (ACN, DMF, DMSO): Often sparingly soluble as neat solvents; DMSO can solubilize many polar compounds and is useful for concentrated stocks that are later diluted into buffer. ACN is mainly used as a mobile-phase modifier rather than a primary solvent for solid dissolution.

Mobile phase considerations for LC–MS (general)

• Typical phases: Water with 0.1% formic acid or ammonium formate/acetate buffers, combined with acetonitrile. NAAG is strongly retained on HILIC and poorly retained on conventional C18 unless highly aqueous conditions or ion-pairing are used.

Comparison (general)

• Water/buffer: maximal solubility and native-like ionization.
• DMSO: strong solvating power for stock solutions; dilute promptly to minimize matrix effects.
• ACN: excellent for precipitation and LC elution strength but limited for initial dissolution of solid NAAG.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Store at -20°C.
• Shipping: Ice chest + Ice pads.

General best practices for this compound class (not item-specific specifications)

• Upon receipt: Allow the sealed container to equilibrate to room temperature before opening to prevent moisture condensation.
• Solid handling: If supplied as a lyophilized solid, promptly reseal under dry inert gas or in a desiccator after use. Multi-acidic peptides can be hygroscopic.
• Reconstitution: Dissolve in high-purity water or aqueous buffer (pH 6.5–8.0). For concentrated stocks, DMSO or water:DMSO mixtures can be used, followed by dilution into buffer before use. Filter through 0.2 µm if needed.
• Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw cycles. Store aliquots at −20°C or below.
• Stability: Avoid prolonged exposure to elevated temperature or extremes of pH. Protect from light if downstream assays are photosensitive.
• Documentation: Record solvent, concentration, and date of preparation on each aliquot. For isotopic work, note the lot number and intended MRM transitions.

Any unstated item-specific limits (e.g., shelf life after reconstitution, water content, isotopic enrichment) are Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Item-specific identifiers (from Product Data)

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

Literature description (general chemistry; not item-specific)

• Spaglumic acid is widely known as N-acetyl-L-aspartyl-L-glutamic acid (NAAG), a dipeptidic derivative of L-aspartate (N-acetylated) and L-glutamate joined through a peptide bond.
• Functional groups: two amide linkages (one peptide, one N-acetyl), three carboxylic acids (α-CO2H of Glu, side-chain CO2H of Glu, side-chain CO2H of Asp). No free α-amino group due to N-acetylation/peptidization.
• Stereochemistry: typically L,L configuration at the α-carbons of Asp and Glu (literature). The deuterated variant denotes isotopic substitution (sites and enrichment not specified for this item).
• 2D structure in words: an N-acetyl group attached to the α-amino of L-aspartate; the α-carboxyl of that aspartate forms an amide bond to the α-amino of L-glutamate; the side chains of Asp (β-CO2H) and Glu (γ-CO2H) remain as free carboxylates.

Notes on the deuterated form

• “-d” indicates one or more hydrogen atoms replaced by deuterium. The labeling pattern and D-content are Not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Scope

• As an isotopically labeled, polyacidic dipeptidic compound, spaglumic acid-d is not typically employed as a general synthetic reagent. Its primary value is as a labeled analog/standard.

Potential utilities (general)

• Isotope tracing: Deuterium incorporation can be used to probe mechanistic aspects of enzymatic hydrolysis (e.g., GCPII-mediated cleavage) by distinguishing substrate, product, and exchange processes via MS.
• Reference in derivatization chemistry: Serves as a test substrate for carbodiimide/NHS ester activation of carboxylates, enabling optimization of labeling conditions for carboxyl-rich metabolites/peptides.
• Calibration of purification: Benchmark for HILIC retention of strongly acidic, zwitterionic small peptides and for method transfer between columns/stations.

Chemical reactivity reminders (general)

• Carboxyl groups: Activatable with EDC/NHS or carbodiimides; prone to forming O-acylisoureas unless trapped by NHS or similar.
• Amide bonds: Resistant to mild conditions but hydrolyze under strong acid/base or in the presence of peptidases.

When a synthesis-grade reagent is needed (e.g., for coupling chemistry), purchase dedicated coupling agents or unlabeled building blocks; the present deuterated material is best conserved for analytical roles.

Target Specificity

Not applicable to this product type.

• This item is a small-molecule, deuterated analog intended for research and analytical use. It is not an antibody, probe, or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype applies.

If you require a binding reagent targeting enzymes involved in NAAG metabolism (e.g., GCPII), please refer to antibody or inhibitor products specifically designed for that purpose.

Domande frequenti

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

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 S1439995, the molecular formula is C11H13D3N2O8, and the molecular weight is 307.27 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.