등급 & 순도UltraBio™?UltraBio™ — Aladdin's line for molecular-biology applications. Use for nuclease-free, high-consistency reagents across molecular workflows.Ultra pure?Ultra-pure grade with very low impurity content across the board. Use for trace analysis, electronics, or processes intolerant of contamination.
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
External Descriptors
Other amino acids
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.
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Application Protocols
Not applicable. No manufacturer-validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. Usage protocols will depend on the intended research application:
Preparing stock solutions: Dissolve in water or buffer (pH 6–8); for high concentration, adjust pH with NaOH to form the pyroglutamate salt. Filter-sterilize (0.22 µm) for cell-free biochemical assays if needed.
Peptide coupling: Activate the carboxyl group with your coupling system of choice (e.g., EDC/Oxyma, HATU/DIPEA) and couple to the amine-bearing substrate under inert atmosphere as appropriate.
Refer to current literature and your institutional SOPs for detailed, application-specific procedures.
Biological Roles
General biology (literature):
Metabolic intermediate: L-Pyroglutamic acid (L-5-oxoproline) is a key intermediate in the γ-glutamyl cycle, linking glutathione turnover to glutamate homeostasis. 5-Oxoprolinase converts 5-oxoproline to L-glutamate in an ATP-dependent step.
Origin: Forms non-enzymatically from cyclization of glutamyl residues or enzymatically via γ-glutamyl cyclotransferase, particularly from γ-glutamyl peptides during glutathione metabolism.
Protein/peptide chemistry: N-terminal glutamine or glutamate residues in peptides can cyclize to pyroglutamate, influencing peptide stability, receptor interactions, and resistance to aminopeptidases.
Transport/charge state: Exists predominantly as a zwitterion in aqueous environments near acidic to neutral pH, affecting membrane transport and chromatographic behavior.
Experimental implications:
Standards and controls: Frequently used as a standard in assays probing glutathione cycle enzymes (e.g., 5-oxoprolinase, γ-glutamyl transpeptidase) and in studies of non-enzymatic cyclization of peptides.
Analytical detection: Detectable by amino acid analyzers after derivatization; in LC-MS, retention aligns with small polar acids; negative-mode ESI typically gives strong deprotonated ions.
Note: The above describes biochemical roles and laboratory relevance only. This product is supplied strictly for research use (per Product Data: For research use only).
Buffer Applications
Not typically used as a primary buffering agent. L-Pyroglutamic acid is a monocarboxylic acid with a single acidic pKa (~2.3–2.6, literature), providing minimal buffering capacity near neutral pH.
Practical guidance:
For preparing aqueous solutions or assay media, select established buffers (e.g., phosphate, HEPES, MOPS, Tris) compatible with your enzymatic or analytical system, and dissolve L-pyroglutamic acid therein.
If higher solubility is required, adjust the medium slightly basic (pH 7–8) to form the pyroglutamate anion; buffering should still be provided by an external buffer system.
Reference notes:
Buffer recipes and pH ranges are buffer-dependent; consult standard buffer tables. L-Pyroglutamic acid itself is better treated as a solute or substrate rather than a buffer component.
Green Alternatives
Context: L-Pyroglutamic acid is a solid chiral building block, not a volatile organic solvent. Greener considerations focus on solvent choices and protecting-group strategy during its use.
Greener handling strategies (literature/general):
Aqueous media: Favor water or water-rich mixtures for dissolution, biocatalysis, and coupling when compatible (e.g., EDC-mediated couplings in buffered aqueous-organic systems).
Coupling reagents: Prefer newer additives (e.g., OxymaPure) over HOBt to reduce explosive hazard; explore EDC/Oxyma or CDI in greener solvents.
Solvent selection: Replace DMF/NMP with alternatives like 2-MeTHF (for non-aqueous steps) or Cyrene when feasible; for analytical work, increase aqueous content in LC eluent.
Energy efficiency: Conduct reactions at ambient temperature with catalytic activation and shorter cycle times; use microwave only when it reduces total energy use and waste.
Trade-offs (comparison, general):
Water vs DMF: Water improves safety and EHS profile but may reduce solubility and coupling efficiency; buffer salts can complicate workup.
2-MeTHF vs DMF: 2-MeTHF is bio-derived and lower toxicity but may not dissolve salts/zwitterions; phase-transfer or co-solvents may be required.
EDC/Oxyma vs HATU: Safer profile and aqueous compatibility vs generally higher reactivity of HATU; reaction times may increase with greener systems.
Waste minimization:
Use stoichiometric balance to limit excess coupling reagents; implement in-line scavenging and aqueous workups that reduce halogenated solvent use.
Pharmaceutical Uses
No therapeutic claims are made. The following reflects manufacturing/formulation context from literature/general practice:
Peptide manufacturing: The pyroglutamyl (pGlu) residue is introduced at the N-terminus of peptides to modulate metabolic stability and enzymatic resistance. L-Pyroglutamic acid serves as the chiral acid component for coupling during synthesis (solution or solid phase).
Excipients/auxiliaries: While not a common pharmacopeial excipient, its salts/derivatives may be used as reference standards or intermediates during process development for peptide APIs.
Quality expectations: For GMP settings, identity confirmation (e.g., chiral HPLC, specific rotation), chiral purity, residual solvent, and trace metals are typically controlled. This product is designated UltraBio™, Ultra pure; for any GMP application, suitability and additional qualifications must be established by the user.
Regulatory note:
This catalog item is for research use only (per Product Data). Any application in regulated manufacturing would require separate qualification, supplier auditing, and compliance with relevant pharmacopeial/ICH guidelines as applicable.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
pKa (carboxyl): ~2.3–2.6 (literature). The ring lactam nitrogen is non-basic; no titratable amine near neutral pH.
Isoelectric behavior: Tends to be zwitterionic near low pH; overall net negative only above the carboxyl pKa (literature qualitative description).
Solubility: Freely soluble in water; limited solubility in common organic solvents (ethanol, methanol) due to polarity; improved solubility in aqueous base (forming the pyroglutamate) (literature).
LogP (XlogP3-AA): approximately −1 to −0.6 (literature estimates), reflecting high hydrophilicity.
Optical rotation: [α]D can be observed in aqueous solution consistent with L-configuration; magnitude depends on concentration/solvent (literature, method-dependent).
Practical notes:
Solutions are best prepared in water or buffer; dissolution is accelerated by mild warming and pH adjustment to 7–8 (literature/lab practice).
Hygroscopicity is low to moderate; keep container tightly closed to limit moisture uptake (general handling guidance).
Always verify item-specific data and release limits on the CoA for your lot.
Quality and Grades
Item-specific grade:
UltraBio™, Ultra pure (from Product Data)
What this typically implies (general guidance):
UltraBio/Ultra pure grades are intended for demanding life-science workflows (e.g., biochemistry, enzyme assays, cell-free systems) where trace ionic and organic contaminants can impact results. Such grades generally feature high chemical purity and low bioburden/trace metals, along with tight control of residual solvents and adventitious organics. Exact acceptance criteria are lot-specific—consult the CoA/Specification Sheet.
Considerations for L-Pyroglutamic acid in life-science use:
End-use sensitivity: In enzyme assays (e.g., studying the γ-glutamyl cycle), trace amines, amides, or metals could bias kinetics. An UltraBio grade helps minimize such interference.
Chromatography: For analytical and prep HPLC of pyroglutamyl peptides or standards, high purity reduces baseline artifacts and unidentified peaks.
Peptide chemistry: Impurities that racemize or acylate can seed side products; ultra-pure starting material supports cleaner coupling profiles.
Stabilizers/Additives:
Not specified for this item; refer to CoA/Spec Sheet for any stabilizers or residual solvent limits.
Verification and documentation:
Each lot should be accompanied by a Certificate of Analysis detailing assay, identity (e.g., NMR/IR/LC-MS/HPLC), and relevant impurities. Always cross-check the CoA for exact specifications used to release your lot.
Reaction and Applications
Representative uses of L-Pyroglutamic acid (literature/general):
Peptide chemistry: Building block for N-terminal pyroglutamyl (pGlu) residues. The lactam ring confers resistance to exopeptidase cleavage and modulates peptide conformation. Coupling typically proceeds via activation of the carboxylate with EDC/HOBt, HATU, or DIC/Oxyma.
Chiral pool precursor: The single stereocenter offers a handle for synthesizing enantioenriched pyrrolidone derivatives and for elaboration to L-glutamic acid derivatives by selective ring opening.
Ring-opening transformations: Hydrolysis under basic or enzymatic conditions affords L-glutamate or derivatives; nucleophiles (e.g., alcohols, amines) can open the lactam under forcing conditions to give ester- or amide-functionalized glutamates.
Protecting-group strategies: The cyclic lactam can function as a masked glutamic acid, unmasked by hydrolysis when desired; the carboxyl group can be selectively protected (e.g., as methyl/tert-butyl ester) to control reactivity.
Analytical standard: Used as a reference compound for studying the γ-glutamyl cycle and 5-oxoprolinase activity; also as a calibration standard in amino acid analysis (derivatization may be required).
Practical tips:
Maintain stereointegrity: Use mild coupling conditions (≤25 °C, neutral to slightly basic) to minimize racemization.
Solubility management: Dissolve in water, minimal base, or DMF; for aqueous reactions, adjust pH to 7–8 to fully solubilize as the pyroglutamate.
Avoid unnecessary strong base or prolonged high temperature unless ring opening is intended.
Reaction Conditions
General laboratory conditions (literature/examples; adjust to your system):
Amide coupling (to amines/peptides):
Solvent: DMF or DMF/DCM; greener alternatives include water/MeCN with EDC/Oxyma.
Temperature/time: 0–25 °C, 1–4 h (monitor by LC/MS). Maintain pH 7–8 in aqueous systems to ensure solubility.
Notes: Minimize base to limit racemization; pre-activation (e.g., NHS ester) can improve coupling to sterically hindered amines.
Hydrolytic ring opening to L-glutamate derivatives:
Base-catalyzed: Aqueous NaOH or Na2CO3 (0.1–1.0 M), 25–80 °C, 0.5–6 h; yields L-glutamate salts. Work up by neutralization and ion-exchange or RP-HPLC.
Acidic: Concentrated mineral acids at reflux effect opening but risk side reactions; base is generally preferred for stereointegrity.
Esterification of the carboxyl group:
Fischer conditions: ROH/H+, reflux; or DCC/DMAP with ROH in DCM/DMF at 0–25 °C.
Formation of activated esters (NHS, pNP):
DCC (1.1 eq) with NHS (1.1 eq) in DCM/DMF at 0–25 °C, 1–3 h; filter urea byproduct; use promptly to couple.
These are literature-style guidelines. Optimize stoichiometry, solvent, and temperature for your substrate scope and scale. Always confirm stereochemistry post-reaction (e.g., chiral HPLC).
Safety and Handling
Item-specific hazard data:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.
General safety considerations for amino acid derivatives (literature/good lab practice):
Expected low acute toxicity; may cause mild eye/skin/respiratory irritation upon contact with dust.
Avoid generating dust; use local exhaust or work in a fume hood during weighing to minimize inhalation exposure.
PPE and handling:
Wear safety glasses with side shields, lab coat, and appropriate gloves (e.g., nitrile). Consider a dust mask/respirator if dust cannot be controlled.
Avoid contact with strong oxidizers and strong bases/acids that could promote degradation or hydrolysis if not intended.
First-aid overview (summary; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
Ingestion: Rinse mouth; seek medical advice if unwell.
Storage incompatibilities and stability:
Store tightly closed at room temperature (per Product Data), in a dry place away from reactive chemicals. Protect from prolonged humidity to avoid caking and from microbial contamination in solution.
Waste disposal:
Dispose of in accordance with institutional, local, and national regulations; aqueous solutions can typically be collected as nonhalogenated aqueous waste unless contaminated.
Solvent Selection
Context: L-Pyroglutamic acid is a polar, zwitterion-forming organic acid; as a solid substrate/reagent it is not used as a solvent. Solvent selection here pertains to dissolving and processing this compound.
Polarity and miscibility (literature/general):
Strongly hydrophilic; best dissolved in water or aqueous buffers.
Solubility in neat organic solvents is limited; protic solvents (MeOH, EtOH) dissolve it modestly; DMSO can be used for concentrated stocks when water is unsuitable.
Typical dissolution choices:
Water or buffer (pH 6–8): Rapid dissolution; ionic strength and pH can be tuned to manage charge state and compatibility with downstream assays.
Mild aqueous base (e.g., NaHCO3, NaOH ≤0.1 M): Forms the soluble pyroglutamate salt for higher-concentration stocks.
Aqueous-organic mixtures: For peptide coupling or analytical workflows, water/MeCN or water/MeOH blends assist in handling and injections.
DMSO: Useful for small-volume, high-concentration stocks for screening; dilute into aqueous media to minimize final DMSO content.
Selection guidance and comparisons:
For biochemistry/enzymology: Choose buffering systems (phosphate, HEPES) that do not interfere with your assay readout; maintain ionic strength consistent with physiological conditions when needed.
For peptide synthesis (solution phase): Use polar aprotic solvents (DMF, NMP) for coupling steps; dissolve the acid with base and coupling reagents (e.g., DIPEA/EDC) as needed.
Avoid strong acids/bases unless hydrolysis or ring-opening is intended.
Storage and Reconstitution
Item-specific storage:
Storage Conditions: Room temperature (from Product Data). Keep container tightly closed in a dry, well-ventilated place.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/good practice):
Solid stability: Store away from moisture and reactive chemicals. Under normal laboratory conditions, the solid is stable for extended periods. Record open date and manage by first-in/first-out.
Reconstitution/dissolution:
Solvents: Water or aqueous buffer preferred. For concentrated stocks, adjust pH to 7–8 with NaOH to form the soluble pyroglutamate salt. DMSO can be used when water is unsuitable.
Typical concentrations: 10–200 mg/mL in water/base depending on application and solubility requirements (optimize empirically).
Sterile solutions: Prepare using sterile water and 0.22 µm filtration for sensitive biochemical assays.
Solution stability: Aqueous solutions are best prepared fresh. For short-term storage, refrigerate (2–8 °C) in clean, closed vials; avoid microbial contamination. For longer storage, aliquot and freeze; minimize freeze–thaw cycles.
Research use note:
For research use only (per Product Data). Verify compatibility of any additives (buffers, bases) with downstream applications and analytics.
Structure and Identity
Overview: L-Pyroglutamic acid (also known as L-5-oxoproline) is the cyclic imide (lactam) formed by intramolecular condensation of L-glutamic acid, retaining the L-configuration at C-2 of the five-membered ring.
Item-specific (from Product Data):
CAS: 98-79-3
PubChem CID: 7405
InChIKey: 254882 (as provided)
Grade/Purity: UltraBio™, Ultra pure
Storage Conditions: Room temperature
Literature/Computed identifiers and descriptors (for reference only):
Five-membered cyclic amide (2-pyrrolidone) ring with two carbonyls (a lactam C=O within the ring and a pendant carboxylic acid).
One stereogenic center at the ring’s C-2 (L-configuration; S by CIP).
Functional groups: secondary lactam, carboxylic acid; capable of existing as a zwitterion in water.
Notes:
The provided InChIKey format is atypical; consult the CoA/SDS for the exact identifier used for this lot.
Synthetic Utility
Functional-group profile and reactivity (literature/general):
Carboxylic acid: Amenable to standard peptide-coupling chemistries (EDC/HOBt, HATU/DIPEA, DIC/Oxyma). Formation of active esters (e.g., NHS esters) enables conjugation to amines on biomolecules or surfaces.
Lactam (2-pyrrolidone) ring: Generally stable toward mild acids/bases; can undergo nucleophilic ring opening under stronger conditions to afford L-glutamate derivatives, enabling access to bifunctional scaffolds.
Stereocenter: Provides chiral induction in transformations at the α-carbon; racemization is minimized under neutral to slightly basic, low-temperature coupling conditions.
Applications:
N-terminal capping: Installation of L-pyroglutamyl residues in peptides/proteins (chemical or spontaneous cyclization from Gln/Glu) to modulate stability.
Chiral building block: Diversification at C-3 via enolate chemistry (under carefully controlled basic conditions) to access substituted pyrrolidones and downstream amino acids.
Prodrugs/conjugates: Activation of the carboxyl (mixed anhydrides, carbonyl diimidazole) to form amide/ester linkages with drugs or probes for targeted delivery/stability studies.
Practical notes:
Protecting groups: If orthogonal protection is needed, prepare esters (e.g., Me, tBu) or convert to pyroglutamyl chloride/anhydride cautiously. Monitor for racemization.
Workup/purification: Due to polarity, products are often purified by reverse-phase chromatography or ion-exchange; lyophilization from aqueous media is effective for isolation.
Target Specificity
Not applicable. This product is a small-molecule amino acid derivative, not an antibody, enzyme, or affinity reagent. No target specificity, clone, isotype, or species reactivity data are associated with this item.
자주 묻는 질문
What does UltraBio? mean?
UltraBio? indicates that the product has been processed and tested for biological and biochemical applications. Specifications may include endotoxin limits, microbial controls, sterility, low DNase/RNase/protease activity, and verified biological activity where relevant.
What does Ultra pure mean?
Ultra pure is a defined analytical purity tier suitable for general analytical and reagent applications. It specifies a minimum assay percentage, controlled limits on common impurities (water, heavy metals, residue on ignition), and lot-to-lot consistency. Ultra pure is one of several purity tiers — choose based on the sensitivity and regulatory requirements of your method.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 98-79-3, the molecular formula is C5H7NO3, and the molecular weight is 129.11 g/mol. InChIKey ODHCTXKNWHHXJC-VKHMYHEASA-N.
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.
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.
