Hydroxyglutamic acid , CAS No.3157-41-3

CAS: 3157-41-3 Cat. No.: H1018987 Formula: C₅H₉NO₅ Peso molecolare: 163.130 Numero EC: EINECS208-572-5

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: C(C(C(=O)O)N)C(C(=O)O)O
• IUPAC Name: 2-amino-4-hydroxypentanedioic acid
• InChIKey: HBDWQSHEVMSFGY-UHFFFAOYSA-N
• INCHI: 1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)
• Peso molecolare: 163.130

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Glutamic acid and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Glutamic acid and derivatives
• Alternative Parents: Alpha amino acids Short-chain hydroxy acids and derivatives Hydroxy fatty acids Amino fatty acids Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives 1,3-aminoalcohols Secondary alcohols Amino acids Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Glutamic acid or derivatives - Alpha-amino acid - Amino fatty acid - Hydroxy fatty acid - Short-chain hydroxy acid - Alpha-hydroxy acid - Dicarboxylic acid or derivatives - Hydroxy acid - Fatty acid - Fatty acyl - 1,3-aminoalcohol - Secondary alcohol - Amino acid - Carboxylic acid - Primary amine - Primary aliphatic amine - Organopnictogen compound - Alcohol - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Amine - Organic oxide - Organic nitrogen compound - Organooxygen compound - Hydrocarbon derivative - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 163.130 g/mol
• XLogP3: -4.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 163.048 Da
• Monoisotopic Mass: 163.048 Da
• Topological Polar Surface Area: 121.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 168.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, validated application protocols are provided in the Product Data. General suggestions (research use only):

• Stock solutions: prepare 10–100 mM in water or buffer; if needed, dissolve first in minimal DMSO and dilute into aqueous media while mixing to avoid precipitation. Filter sterilize (0.22 µm) for cell-free biochemical assays.
• Peptide coupling: employ standard Fmoc/Boc protection and modern coupling reagents in anhydrous polar aprotic solvents. Verify orthogonality with the chosen hydroxyl protecting group.
• Analytical QC: characterize by 1H/13C NMR (D2O, DMSO-d6 with appropriate pH adjustment), HRMS, and HPLC; for chiral purity use chiral HPLC or derivatization methods (e.g., Marfey’s analysis).

Consult the CoA/Spec Sheet for any available test methods specific to this SKU.

Biological Roles

Literature/general context (no clinical claims):

• Structural analog of glutamic acid: the added hydroxyl modulates hydrogen bonding and recognition by enzymes and transporters in biochemical studies.
• Occurrence: hydroxyglutamic acid motifs are reported in certain natural products and peptide secondary metabolites; enzymatic hydroxylation of glutamate or glutamyl residues can generate these units in biosynthetic pathways.
• Biochemical utility: serves as a probe to interrogate binding pockets that differentiate between carboxylate positioning and additional hydroxyl functionality; can impact stereoelectronic preferences in active sites (e.g., racemases, aminotransferases) in in vitro assays.
• Ionization/zwitterions: like acidic amino acids, multiple protonation states exist across physiological pH ranges, affecting transporter affinity and enzyme kinetics in cell-free systems.

Caveat: Exact biological behavior is sensitive to isomer (3- vs 4-hydroxy) and stereochemistry (L/D; threo/erythro). For targeted biochemical applications, confirm the isomeric composition provided on the CoA or by independent analysis (e.g., chiral HPLC, NMR).

Buffer Applications

Not typically used as a primary buffering agent. While amino acids display pH-dependent zwitterionic behavior, hydroxyglutamic acid is not a standard Good’s buffer and lacks widely established buffer recipes.

Practical notes (general):

• If employed as a component in custom buffer systems, determine its titration curve empirically for the specific isomer and ionic strength.
• Typical approach: dissolve in water, adjust pH with NaOH/KOH or HCl to the target value, and verify ionic strength/osmolality as needed.
• For robust buffering in the pH 5–8 range, consider established systems (e.g., MES, MOPS, HEPES, phosphate) and use hydroxyglutamic acid only as a co-solute if required for biochemical assays.

Green Alternatives

Context: As a solid amino acid derivative, hydroxyglutamic acid itself is not a solvent; green chemistry considerations focus on protecting-group strategy, solvent choice, and coupling reagents during its use.

Greener choices (literature guidance):

• Solvents:
  • Prefer water or aqueous buffer when feasible (e.g., enzymatic transformations, EDC-mediated couplings at mild pH).
  • Replace DMF/DCM with greener polar aprotics such as N-butylpyrrolidone (NBP), propylene carbonate, or 2-MeTHF for compatible steps; verify solubility of protected derivatives.
• Coupling reagents:
  • Consider less hazardous coupling systems (e.g., DMTMM in water or EtOAc; CDI for certain O- to N-acyl transfers) to reduce waste and avoid explosive additives.
• Protection strategy:
  • Minimize protecting groups by employing orthogonal, removable groups and telescoped steps; use hydrogenolysis (OBn) over strong acid if compatible with the substrate set.

Illustrative comparison (general; not item-specific):

• DMF vs. NBP: similar polarity for amide couplings; NBP offers improved worker safety profile and lower volatility.
• DCM vs. 2-MeTHF/EtOAc: greener alternatives provide reduced toxicity and better lifecycle metrics for extractions and workups.

Note: Validate greener substitutions on small scale to ensure reaction performance (conversion, selectivity, and purity) is maintained.

Pharmaceutical Uses

Formulation/manufacturing context (no therapeutic claims):

• Hydroxyglutamic acid is primarily a research chemical and specialized building block; it is not a common pharmacopeial excipient.
• Potential roles in R&D: chiral intermediate for synthesis of amino-acid–derived APIs or peptidomimetics; tool compound in screening assays probing glutamate-recognizing enzymes or transporters (in vitro only).
• Salt selection: preparation of sodium/potassium salts can enhance aqueous handling during process development studies.

Compliance: This product is labeled For research use only. It is not intended for human or veterinary use, clinical diagnostics, or as a drug substance/excipient without appropriate qualification and regulatory review.

Physical Properties

Item-specific specifications (from Product Data):

• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Storage: Room temperature (as provided).

Literature/general properties for hydroxyglutamic acid (qualitative; not item specifications):

• Physical state: typically solid, highly polar, and crystalline; many amino acid derivatives exhibit high melting points with decomposition.
• Solubility: readily soluble in water; very limited solubility in nonpolar organic solvents; solubility in polar protic solvents (e.g., MeOH) may be modest and pH-dependent. Salt formation (Na+, K+) usually increases aqueous solubility.
• Acid–base behavior: triprotic amino acid behavior (two carboxyl groups and one amino group) plus a non-ionizable aliphatic hydroxyl. Exhibits multiple pKa values typical of acidic amino acids; exact values depend on isomer and ionic strength (literature).
• Partitioning: expected very low logP and high logD sensitivity to pH due to zwitterionic character; negligible volatility.
• Optical activity: chiral at the α-carbon; specific rotation depends on enantiomeric composition and isomer.

Do not treat the above as product specifications; consult the CoA/Spec Sheet for item-specific numerical data (mp, solubility, pKa, optical rotation, water content, etc.).

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance (general):

• Without a declared grade (e.g., BioReagent, ≥98%, HPLC, or peptide-synthesis grade), users should verify suitability for their application by reviewing the CoA/Spec Sheet and performing fit-for-use checks (e.g., residual solvent profile, ash/metals, optical purity, and chromatographic purity).
• For peptide work, typical desirable controls include: enantiomeric excess (chiral HPLC), diastereomeric purity (for 3- or 4-hydroxy stereocenters), water content (Karl Fischer), and residual inorganic salts.
• If UV-based analytics are planned, low-UV impurity profiles are preferred (HPLC or LC–MS grade). For biochemical assays, low endotoxin/bioburden may be important; confirm if such attributes are specified on the CoA.
• Stabilizers: none are typically used for amino acids; if any additive is present (e.g., anti-caking), it should be declared on the CoA.

Recommendation: request the latest CoA and SDS for batch-specific assay, identity tests (NMR/IR/HRMS), and impurity limits if your application is sensitive to isomeric composition or trace metals.

Reaction and Applications

Scope (general literature; this item is supplied for research use only):

• Building block in peptide chemistry: hydroxyglutamic acid residues appear in certain natural products and engineered peptides; the hydroxyl adds hydrogen-bonding capacity and a handle for downstream derivatization (e.g., phosphorylation, glycosylation, or etherification) in model systems.
• Chemo-selective transformations:
  • O-functionalization: esterification (e.g., benzyl/TBDMS protection), O-acylation or O-alkylation under carefully controlled conditions to avoid N-acylation; Mitsunobu-type etherification on protected derivatives.
  • Sidechain carboxyl activation: formation of active esters/anhydrides; amide coupling to form isopeptide linkages.
• Synthesis of analog libraries: used to probe structure–function relationships in enzymes recognizing glutamate/glutamate-like substrates (e.g., racemases, transaminases) in biochemical assays.
• Chiral pool applications: the α-stereocenter provides a platform for asymmetric synthesis; diastereomerically pure hydroxyglutamate can serve as a synthon for densely functionalized building blocks.

Practical tips:

• For solution-phase peptide coupling, protect the α-amine (Fmoc/Boc), protect carboxyl groups as esters (OtBu/OBn) and consider temporary protection of the hydroxyl (TBDMS, TBS, or benzyl) to direct chemoselectivity.
• Use modern coupling systems (e.g., HATU/HOAt, HBTU/HOBt alternatives such as Oxyma) in DMF/MeCN with a hindered base (DIPEA). Control temperature to minimize epimerization.
• For aqueous bioconjugation, activate carboxylates with EDC/NHS in buffered media (pH 5.0–6.5) and quench appropriately.

Reaction Conditions

General guidance for typical transformations (literature; not item-specific):

• Amide bond formation (solution phase):
  • Solvent: DMF, NMP/NBP, or MeCN; for greener options consider NBP or EtOAc (with soluble coupling systems).
  • Reagents: HATU or TBTU with DIPEA; or EDC·HCl with Oxyma/DHBT in mildly basic media. Temperature: 0–25 °C; time: 0.5–12 h depending on sterics.
  • Notes: Protect the hydroxyl to suppress undesired O-acylation or control chemoselectivity.
• Aqueous carboxyl activation for bioconjugation:
  • Buffer: MES or phosphate, pH 5.0–6.5.
  • Reagents: EDC with NHS or sulfo-NHS; temperature: ambient; time: 15–120 min.
  • Quench unreacted active ester to reduce background labeling.
• O-alkylation/O-acylation on protected derivatives:
  • Base: NaH or K2CO3 (for Mitsunobu-type, use DEAD/DIAD and PPh3); solvent: THF/DMF; temperature: 0–25 °C.
  • Ensure N-protection (Fmoc/Boc) and carboxyl protection to avoid competing pathways.
• Deprotection:
  • Fmoc removal: 20% piperidine in DMF, rt, 5–20 min.
  • Boc/OtBu removal: TFA in DCM (95:5), 0–25 °C, 0.25–2 h.
  • OBn deprotection: hydrogenolysis (H2, Pd/C, 1–10 bar), MeOH/EtOH, rt–40 °C.

Always monitor by LC–MS/HPLC and confirm stereochemical integrity (avoid epimerization at the α-carbon under strong base or high temperature).

Safety and Handling

Item-specific hazard information (from Product Data):

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for amino acids and their hydroxy analogs (literature/typical):

• Expected hazards: low acute toxicity profile is common, but dust may cause mechanical irritation to eyes/respiratory tract. Avoid inhalation of dust and contact with eyes/skin.
• PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use dust control (weighing in a fume hood or balance enclosure).
• Handling: minimize dust formation; avoid contact with incompatible reagents (strong oxidizers, strong acids/bases during storage, and acylating/alkylating agents if unprotected functional groups are to be preserved).
• First aid (overview; consult SDS for details): rinse eyes/skin with water for several minutes if contacted; move to fresh air if inhaled; seek medical attention if symptoms persist.
• Spills: collect solids with minimal dust generation; wash area with water. Dispose of in accordance with institutional and local regulations.
• Thermal stability: amino acids often char/decompose rather than melt; avoid overheating during drying.

Always consult the product-specific SDS for authoritative hazard classification, exposure limits, and response procedures.

Solvent Selection

Relevance: Hydroxyglutamic acid is a highly polar, polyfunctional amino acid derivative. Solvent choice is dominated by acid–base and hydrogen-bonding considerations.

General guidance (literature/typical):

• Polarity/miscibility: readily soluble in water and aqueous buffers; poor solubility in most aprotic organics (e.g., Et2O, hexanes, toluene). Solubility in polar organics (MeOH, EtOH, DMSO) is variable and strongly pH-dependent.
• Working solvents:
  • Aqueous media: preferred for analytical work, biochemistry, and ion-exchange purification. Adjust pH to achieve desired ionic form.
  • DMSO: good co-solvent for preparing concentrated stock solutions; dilute into buffer immediately to minimize precipitation.
  • Alcohols: limited use; often require mild base to enhance dissolution.
• Salt form: converting to alkali metal salts (Na+, K+) typically increases aqueous solubility and handling.

When to choose alternatives:

• If nonaqueous peptide coupling is planned, use protected derivatives (e.g., Fmoc-/Boc-protected hydroxyglutamic acid esters) that are soluble in DMF/DCM rather than the free amino acid.
• For crystallization or solvent exchange, water/ethanol mixtures or water–acetone with pH control can be effective.

Tip: Filter all working solutions (0.22–0.45 µm) to remove particulates prior to analytical or biological assays.

Storage and Reconstitution

Item-specific storage (from Product Data):

• Store at: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General handling and stability (literature/typical for amino acids):

• Protect from moisture to prevent caking and variable water content; store tightly closed in a desiccator if possible.
• Light/heat: store away from direct light and heat sources; many amino acids are stable at ambient temperature but decompose on strong heating.
• Shelf life: verify batch-specific retest/expiry on the CoA.

Reconstitution guidance (general):

• Solvents: water or aqueous buffers are preferred. Adjust pH to enhance solubility if needed; mild warming (≤40 °C) may aid dissolution.
• Stocks: prepare at defined concentration (e.g., 10–100 mM), filter sterilize if required, and aliquot to minimize freeze–thaw (if storing refrigerated or frozen).
• Storage of solutions: short-term at 2–8 °C; for longer-term, freeze at −20 °C or below. Inspect for precipitation or microbial growth before use.

Note: For exact hygroscopicity, water content, and stability data for this SKU, consult the CoA/Spec Sheet and SDS.

Structure and Identity

Brief overview: Hydroxyglutamic acid is a hydroxylated derivative of glutamic acid, i.e., an acidic, highly polar amino acid bearing an additional hydroxyl group on the carbon backbone. Multiple regioisomers (e.g., 3- or 4-hydroxy) and stereoisomers (threo/erythro; D/L) are known in the literature.

Item-specific (from Product Data):

• SKU: H1018987
• Product name: Hydroxyglutamic acid
• CAS: 3157-41-3
• PubChem CID: 839
• InChIKey: 116897 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/General identity notes (not item-specific):

• Common empirical formula reported for hydroxyglutamic acid derivatives: C5H9NO5 (literature; may vary with salt/hydration state and specific isomer).
• Core functional groups: α-amino (–NH2/–NH3+ depending on pH), α-carboxyl (–COOH/–COO−), γ-carboxyl (–COOH/–COO−), and one aliphatic hydroxyl (–OH).
• Structural features: an acyclic, five-carbon backbone; the α-carbon is stereogenic (L/D), and the carbon bearing the hydroxyl may introduce additional stereocenters depending on position/configuration.
• 2D description: HOOC–CH(NH2)–CH(R)–CH2–COOH, where R = OH placement depending on isomer (e.g., R = OH at C3 for 3-hydroxy). Protonation state is pH-dependent (zwitterionic near neutral pH).

Note: Exact isomeric form, stereochemistry, and structure for this catalog item are not specified; consult the CoA/SDS for definitive structural identifiers and analytical data.

Synthetic Utility

Key functional elements and reactivity (general literature):

• α-Amino and diacid functionality: enables peptide bond formation, isopeptide coupling via the sidechain carboxylate, and formation of cyclic derivatives (e.g., lactams) under dehydrating conditions.
• Aliphatic hydroxyl: provides orthogonal reactivity for O-derivatization (e.g., O-alkyl/O-acyl) and late-stage functionalization (e.g., phosphorylation mimics for mechanistic studies).
• Protecting group strategy: typical orthogonal sets include Fmoc (Nα), OtBu/OBn (carboxylates), and TBDMS/TBS or benzyl ethers (alcohol). The order of deprotection can be tuned to drive chemoselective couplings.
• Chiral pool: enantiopure hydroxyglutamic acid provides access to densely functionalized scaffolds with defined relative/absolute stereochemistry useful in natural product analog synthesis.

Applications:

• Assembly of hydroxyglutamate-containing peptides and peptidomimetics for SAR studies.
• Synthesis of polyfunctional building blocks via selective activation of one carboxyl group (e.g., mixed anhydrides, NHS esters) while masking others.
• Preparation of metal-chelating ligands exploiting vicinal –OH/–COO− arrays for coordination studies (inorganic/analytical contexts).

Target Specificity

Not applicable. This product is a small-molecule amino acid derivative, not an antibody, protein, or targeted biological reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.