This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
175.140 g/mol
XLogP3
-1.400
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Exact Mass
175.048 Da
Monoisotopic Mass
175.048 Da
Topological Polar Surface Area
104.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
200.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No item-specific, validated protocols are provided in the Product Data. The following general research-use examples illustrate typical workflows; adapt to your lab’s SOPs.
Preparation of LC–MS stock solution (general):
Accurately weigh an appropriate amount into a clean vial.
Add water or water/acetonitrile (≥80:20) to achieve 1–10 mg/mL; sonicate briefly if needed. Adjust pH slightly basic (pH 7.5–8.5) to ensure dissolution. Filter 0.22 µm.
Store aliquots at 2–8°C for short-term or at −20°C for extended periods; avoid repeated freeze–thaw.
SPE cleanup for polar metabolites (general):
Use mixed-mode anion-exchange cartridges. Condition with MeOH and water, load aqueous sample, wash with water (and 5–10% MeOH), elute with 2% formic acid in 50–80% MeOH or with ammonium bicarbonate in 50% MeOH. Dry under N2 and reconstitute in initial LC mobile phase.
Coupling to an amine (small-scale, general):
Dissolve succinylglycine (1.0 equiv) and amine (1.2–1.5 equiv) in DMF or water/DMF. Add EDC (1.1 equiv) and Oxyma or NHS (1.2 equiv) at 0–5°C, then stir at 20–25°C for 2–12 h. Quench, extract or desalinate, and purify by preparative HPLC.
These are illustrative only; optimize for your system.
Biological Roles
Literature/general information: Succinylglycine is an acylglycine, formed by conjugation of succinyl-CoA (or succinate-derived acyl species) to glycine via glycine N-acyltransferase activity. It belongs to a broader class of glycine conjugates involved in intermediary metabolism and detoxification of acyl groups.
Biochemical context:
Represents a terminal product of acyl group transfer to glycine, increasing water solubility of dicarboxylic acyl species.
The molecule is dianionic at physiological pH (carboxylates), favoring renal handling and aqueous compartmentalization in biological systems.
Analytical relevance:
Frequently included in metabolite panels for organic acid and acylglycine profiling by LC–MS/MS.
Serves as a benchmark for evaluating extraction recovery of polar, multiply ionizable metabolites from biofluids.
Transport/chemistry:
The amide linkage is relatively stable under physiological conditions; hydrolysis typically requires enzymatic or strong chemical conditions.
Note: The above describes general biochemical roles reported in the literature and is provided for research context only. It does not imply any diagnostic, clinical, or therapeutic use.
Buffer Applications
Succinylglycine is not a conventional buffering agent. Although it contains two carboxyl groups, its pKa values and amphoteric character are not standardized for buffer preparation, and it is not commonly used to maintain pH in biochemical assays.
Practical guidance:
For buffering needs in the pH 2–8 range, prefer established buffers (e.g., acetate, phosphate, HEPES, MOPS). Use succinylglycine in such buffers as an analyte or standard rather than as the buffering component.
If preparing analytical standards, adjust solution pH with minimal amounts of dilute base/acid to enhance solubility without relying on intrinsic buffering capacity.
Green Alternatives
This product is a polar small-molecule metabolite/standard, not a process solvent. Green chemistry considerations therefore focus on how it is used rather than substituting the compound itself.
Greener use strategies:
Prefer aqueous media whenever possible (buffered water, bicarbonate/acetate systems) over high percentages of organic solvents.
For LC methods, use water–acetonitrile over water–methanol if energy-intensive drying is anticipated, or choose the solvent aligned with your waste minimization plan.
For coupling reactions, water-compatible coupling agents (e.g., EDC with NHS/HOBt alternatives such as Oxyma Pure) can reduce solvent burden. Employ catalytic DMAP sparingly and avoid chlorinated solvents.
Opt for SPE cartridges that enable aqueous loading and minimal organic elution to reduce solvent volumes.
Comparative perspective:
As a highly functionalized, nonvolatile solid, succinylglycine does not pose the volatility and peroxide-formation concerns of common ethers/solvents; primary environmental footprint arises from auxiliary reagents and solvents used with it.
Waste management:
Collect aqueous waste streams separately; neutralize before disposal per local regulations. Avoid unnecessary salt addition that can complicate wastewater handling.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient grade is provided for this product.
Item-specific information:
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Regulatory listings (USP/EP/JP): Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical):
As a small polar metabolite, succinylglycine may be employed in pharmaceutical analytical labs as a system suitability compound, reference standard for bioanalytical LC–MS/MS methods, or as a polar API impurity analog in method development and validation studies.
Its strong hydrophilicity and negative charge at neutral pH make it useful for challenging-chromatography demonstrations (HILIC/ion-pair or mixed-mode).
All mentions are limited to research, development, and quality-control contexts. This product is for research use only and is not intended for human or animal use in drug products.
Physical Properties
Item-specific specifications are not provided in the Product Data. The following are literature/general characteristics to guide handling and method development. Do not treat as product specifications.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not applicable for a multifunctional organic acid/amide (decomposes before boiling under ambient pressure; literature trend for related compounds). Specific value not specified for this item.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature expectations):
High aqueous solubility expected due to two carboxyl groups and an amide; readily soluble in water and aqueous buffers across a broad pH range.
Poor solubility expected in nonpolar organic solvents (e.g., hexanes, toluene). Limited solubility in alcohols/acetone may be improved by salt formation or pH adjustment.
Acidity/basicity (literature/general):
Exhibits two acidic carboxyl groups (typical pKa values for dicarboxylic acid derivatives ~2–5) and a nonbasic amide nitrogen; precise pKa values not specified for this item.
LogP/logD (general expectation): Strongly hydrophilic; anticipated negative logP and low logD at neutral pH; not specified for this item.
Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
What to expect for this compound class:
For metabolite standards and library compounds, vendors often control identity by NMR/HRMS and purity by HPLC/GC or qNMR. If your application is quantitative (e.g., LC–MS calibration), request and review the CoA for assay method, residual solvents, water content, and inorganic residue.
Low-UV absorbance background and low nonvolatile residue are helpful for LC–MS workflows; confirm if applicable in the CoA.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. Given the polar, nonvolatile nature of succinylglycine, stabilizers are typically unnecessary; however, confirm absence of buffers or salts if downstream quantitative analysis requires minimal matrix.
Trace specifications (metals, residual solvents, water, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
Suggested incoming QC (user):
Verify identity by 1H/13C NMR in D2O or DMSO-d6; confirm carboxylate signals and amide resonance.
Assess purity by HPLC with ELSD/UV at low wavelength or by LC–MS using negative ESI.
Check water content by KF if dry mass accuracy is critical for standard preparation.
Reaction and Applications
While primarily used as a biochemical standard and small-molecule library member, succinylglycine’s bifunctional carboxylic acid/amide architecture supports several lab applications.
Analytical/standards (general):
Suitable as an LC–MS calibration/reference material for acylglycine profiling and metabolomics workflows. Exhibits strong response in negative-ion ESI as [M–H]−; in positive mode, adduct formation may be modest.
Useful for validating sample preparation of polar metabolites (protein precipitation, SPE with mixed-mode anion exchangers, HILIC method development).
Conjugation chemistry (general):
The terminal carboxyl groups can be selectively activated (e.g., EDC, DIC, T3P) for coupling to amines to form extended amide linkages or labeled derivatives (fluorophores, stable isotopologues).
Succinyl moiety can serve as a spacer to modulate hydrophilicity or introduce a cleavable handle.
Derivatization for GC workflows (general):
Carboxyl groups can be converted to methyl/tert-butyldimethylsilyl esters; amide is typically retained under mild derivatization. Consider two-step derivatization (esterification then silylation) if volatility is required.
Practical considerations:
Maintain pH control during activation to minimize O→N acyl migration or anhydride formation.
For selective mono-activation, protect one carboxyl group or exploit differential reactivity under aqueous carbodiimide conditions.
Include appropriate blanks; carryover can occur in HILIC systems due to strong retention of dianionic species.
Reaction Conditions
General, literature-informed guidance for working with succinylglycine in synthesis and analysis. Treat as method-development starting points, not product specifications.
Amide/ester coupling (carboxyl activation):
Solvent: Water, DMF, or water/DMF mixtures. For fully aqueous media, EDC (0.9–1.2 equiv) with NHS/Oxyma (1.0–1.5 equiv) is effective.
Base/pH control: MES or phosphate buffer pH 5.0–6.5 for EDC/NHS; DIPEA or triethylamine (1–2 equiv) in DMF for DIC/Oxyma.
Temperature/time: 0–25°C, 1–16 h depending on nucleophile; monitor by LC–MS or HPLC.
Salt formation/neutralization:
Prepare sodium or ammonium salts by titrating aqueous solutions with NaOH or NH4OH to target pH 7–9; isolate by lyophilization.
Analytical LC–MS:
Chromatography: HILIC (amide or zwitterionic phases) with acetonitrile-rich mobile phases; or mixed-mode anion-exchange.
Mobile phase: 5–20 mM ammonium acetate/formate, pH 3–6 (positive mode often benefits from formic acid 0.1%); for negative ESI, reduce acid strength to maintain ionization.
Detection: ESI− favored; typical transitions and exact m/z should be determined from your instrument; prepare 0.1–1.0 mg/mL stocks in water and dilute to working levels (1–1000 ng/mL) as needed.
Derivatization for GC:
Convert carboxyl groups to volatile esters (e.g., methanolic HCl or BF3–MeOH), optionally followed by silylation of remaining acidic sites; temperatures 60–80°C, 30–90 min.
Adjust conditions to your substrate and equipment; validate on small scale before scale-up.
Safety and Handling
GHS/SDS information (item-specific):
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-phrases): Not specified for this item; refer to SDS.
Pictograms/classification: Not specified for this item; refer to SDS.
General laboratory precautions (good practice):
Handle in accordance with institutional chemical hygiene plans.
Wear appropriate PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Avoid inhalation of dusts/powders and contact with eyes/skin.
Use local exhaust ventilation when weighing or preparing dry powders/solutions.
First-aid overview (general):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention as needed.
Incompatibilities (general):
Strong oxidizers, strong bases or acids may lead to degradation or salt formation; carbodiimides or strong dehydrating agents can cause undesired condensation.
Thermal/chemical stability (general):
Stable under recommended storage (see Storage & Reconstitution). Avoid prolonged heating; multifunctional carboxylic acid/amides may decompose before boiling.
Waste disposal: Dispose according to local regulations; aqueous solutions can often be collected with organic acid waste streams.
Always consult the product’s SDS for authoritative safety and regulatory details.
Solvent Selection
Succinylglycine is a highly polar, dicarboxylic amide; solvent choice is driven by its acid–base behavior and intended application.
Polarity/miscibility (general):
Readily soluble in water and aqueous buffers over a broad pH range; increased solubility at basic pH due to carboxylate formation.
Sparingly soluble in most aprotic organic solvents; limited solubility in methanol/ethanol can improve with slight basification or by forming alkali salts.
Recommended solvents by application:
LC–MS reference solutions: water, water/acetonitrile, or water/methanol with 0.1–0.5% formic acid (positive-mode methods) or 2–10 mM ammonium bicarbonate/acetate (negative-mode methods). Keep ionic strength minimal for ESI.
NMR: D2O provides clean spectra; DMSO-d6 is an alternative if acidic exchange complicates analysis.
Synthetic activation: Dissolve in water, DMF, or mixed aqueous-organic media; activate carboxyl groups in situ (e.g., EDC/HOBt) when coupling to amines.
Comparison notes:
Versus neutral dicarboxylic acids, succinylglycine typically requires less base to dissolve due to additional polarity from the amide group.
For lyophilization, choose volatile counterions (NH4 +) to facilitate removal after drying.
Practical tips:
Adjust pH to ~7–9 to maximize solubility for stock solutions; filter through 0.22 µm for analytical use.
Avoid high percentages of nonpolar solvents; precipitation may occur upon strong organic dilution.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Shelf life/retention: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling (general guidance):
Solubility: Readily dissolves in water and aqueous buffers; for maximal solubility, adjust to pH 7–9. If preparing highly concentrated stocks, form the sodium or ammonium salt in situ by neutralization.
Stock preparation: Prepare 1–100 mg/mL stock solutions in water or water/organic mixtures (e.g., 90:10 water:acetonitrile) depending on downstream use. Filter through 0.22 µm for analytical applications.
Aliquoting: Divide into single-use aliquots to avoid moisture uptake and contamination of the parent container.
Freeze–thaw: Although storage at room temperature is indicated for the solid, aqueous solutions should be stored refrigerated (2–8°C) for short term or frozen (−20°C or below) for longer term. Minimize freeze–thaw cycles by aliquoting.
Light/air sensitivity: No special precautions generally required for this class; keep containers well closed and protect from prolonged heat or humidity.
Always defer to the product label and CoA/SDS for authoritative storage and handling instructions.
Structure and Identity
Succinylglycine is the N-acyl conjugate of glycine with succinic acid, giving a bifunctional dicarboxylic amide commonly encountered as a polar, zwitterion-capable small molecule metabolite.
Product identifiers (item-specific):
CAS: 5694-33-7
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Composition (literature/general):
Molecular formula (literature): C6H9NO5
Molecular weight (literature): ~175.14 g/mol
Structural features (general description):
Contains a terminal succinate carboxyl group, an amide linkage (–CO–NH–) to glycine, and a terminal glycine carboxyl group.
Typical 2D depiction: HOOC–CH2–CH2–CO–NH–CH2–COOH, with potential internal hydrogen bonding and acid–base equilibria leading to zwitterionic forms in water.
Stereochemistry: None (achiral).
Synthetic Utility
Succinylglycine combines a succinic acid terminus with a glycine terminus linked through a secondary amide, yielding a bifunctional, hydrophilic building block.
Functional handles:
Two carboxyl groups: amenable to standard activation (EDC/NHS, DIC/HOBt alternatives, T3P) to form esters or amides with nucleophiles.
Amide linkage: generally inert under mild conditions, providing a stable spacer while enabling further elaboration at the acid termini.
Selective mono-esterification under Fischer conditions is challenging due to diacid nature; protection strategies (e.g., benzyl esters, orthogonal silyl esters) facilitate regioselectivity.
Amide coupling to primary amines yields extended diacids or multifunctional linkers with defined hydrophilicity.
Formation of dianionic salts (Na+, NH4 +) to modulate solubility and reactivity in aqueous-organic media.
Retrosynthetic value:
Useful as a preformed “succinyl” spacer linked to glycine, enabling rapid access to succinylated amine derivatives without handling succinic anhydride directly in sensitive systems.
Practical tips:
Control pH during coupling (typically pH 5.0–6.0 for EDC-mediated reactions) to limit anhydride formation and O-acylisourea side products.
For orthogonal chemistry, temporarily protect one carboxylate; evaluate chemoselective activation with CDI or mixed anhydrides when needed.
Target Specificity
Not applicable. This product is a small molecule (succinylglycine), not an antibody, probe, or biological macromolecule with immunochemical target specificity. No item-specific target, epitope, clone, or isotype information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
