This compound belongs to the class of organic compounds known as methionine and derivatives. These are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
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
164.230 g/mol
XLogP3
-0.800
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Exact Mass
164.062 Da
Monoisotopic Mass
164.062 Da
Topological Polar Surface Area
101.000 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
110.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
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
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Recensioni
Recensioni dei clienti
Application Protocols
No item-specific tested application protocols are provided in the Product Data.
General preparation for solution stocks (research use)
Dissolve in water, aqueous buffer (pH 6–8), or DMSO to prepare concentrated stocks. Typical working concentrations for biochemical assays may range from low micromolar to millimolar, depending on assay design and metal-chelation endpoints. Filter-sterilize through 0.22 µm if sterility is required.
For metal-binding studies, pre-treat buffers with Chelex or use metal-free water/consumables to minimize background.
Notes on analysis
Monitor by HPLC/UPLC with UV at 210–220 nm and MS detection for confirmation. Reverse-phase gradients (water/MeCN + 0.1% formic or formic acid/ammonium formate systems) generally provide good peak shape.
These are general suggestions only. Develop and validate protocols under your specific laboratory conditions.
Biological Roles
General biochemical context (literature; no medical claims)
Methionine residue: L-Methionine is an essential amino acid involved in protein biosynthesis and as a precursor to S-adenosylmethionine (SAM), the universal methyl donor. In small-molecule derivatives, the methionyl side chain retains the thioether susceptible to reversible oxidation (Met/MetO chemistry) relevant to redox studies.
Hydroxamate motif: Hydroxamates are classical metal chelators with affinity for Fe3+/Fe2+ and other hard cations; they are widely used to model siderophore interactions and to probe metalloenzyme active sites in vitro. The N–OH group also participates in hydrogen bonding, influencing binding and recognition in biochemical assays.
Charge state and solubility: At physiological pH, the α-amine is largely protonated while the hydroxamate N–OH is weakly acidic; the balance of ionization states modulates membrane permeability and protein binding. Salt forms can be used to tune solubility for assay preparations.
Utility in research settings
Serves as a ligand/competitor in metal-binding assays, a substrate analog to explore peptide/hydroxamate interactions, or a redox probe for methionine oxidation chemistry.
Note: This product is designated for research use only. No clinical, diagnostic, or therapeutic use is intended or implied.
Buffer Applications
This compound is not a standard biological buffer component.
Practical notes
Although the hydroxamate N–OH is weakly acidic and the α-amine is basic, N-Hydroxy-L-methioninamide is not employed as a primary buffering agent. If used in aqueous assays, prepare in an appropriate buffer (e.g., phosphate, HEPES, or acetate) chosen for pH, ionic strength, and metal content compatible with hydroxamate chelation studies.
For metal-binding experiments, use buffers with minimal metal contamination and known complexation behavior; avoid Tris/imidazole if their metal chelation competes with hydroxamate binding unless that is part of the experimental design.
Green Alternatives
While N-Hydroxy-L-methioninamide is a reagent/building block rather than a solvent, its handling and process choices can be optimized for greener chemistry.
Solvent selection (greener choices)
Prefer water, ethanol, isopropanol, and acetonitrile (with proper waste handling) over chlorinated solvents. For high solubility needs, biobased 2-MeTHF or Cyrene may substitute DMF/DMSO in some derivatizations, subject to compatibility.
Oxidation/derivatization alternatives
For controlled thioether oxidation, consider H2O2 in water/alcohol with catalytic tungsten or titanium systems as greener alternatives to peracid oxidants; monitor to avoid over-oxidation.
For acylations, employ enzyme-mediated or carbodiimide-free coupling strategies (e.g., CDI, green coupling additives) when feasible to minimize urea waste.
Workup and purification
Favor aqueous crystallization or reverse-phase chromatography with water/alcohol eluents. Minimize halogenated solvent use and use in-line scavengers to reduce solvent volumes.
Comparative summary (general)
Conventional: DMF/DMSO, mCPBA, dichloromethane.
Greener alternatives: Water/EtOH/i-PrOH, 2-MeTHF/Cyrene (case-dependent), aqueous H2O2 systems, ethyl acetate as a workup solvent.
Trade-offs: Greener solvents may alter solubility or reaction rates; hydroxamate chelation can sequester catalytic metals differently in protic media. Perform small-scale trials to validate replacements.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient role is provided.
General formulation/processing context (no therapeutic claims)
Hydroxamate-bearing amino-acid derivatives can serve as research intermediates or linker/ligand fragments during discovery-scale synthesis. Their strong metal-binding capacity can be leveraged in purification (affinity capture) or as handles for immobilization on resins.
If incorporated into prototype formulations for research, consider salt formation (e.g., hydrochloride) to enhance aqueous solubility and control hygroscopicity; verify stability of the thioether against oxidation during processing and storage.
No USP/EP monograph is known for this specific derivative (literature check advisable if regulatory use is contemplated). For any GMP-related use, comprehensive characterization (identity, purity, residual solvents, metals, water) and stability data would be required.
Given the product’s research-use designation, all applications should remain within non-clinical, laboratory-scale contexts.
Physical Properties
Item-specific physicochemical specifications are not provided in the Product Data.
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index, water/peroxide/metal limits, UV cut-off: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations (non-binding, for planning only)
As an amino-acid hydroxamate, the compound is expected to be a polar, crystalline solid with good aqueous solubility at neutral to slightly basic pH due to the primary amine and hydrogen-bonding hydroxamate group.
Hydroxamate N–OH typically exhibits weak acidity (pKa for N–OH in simple hydroxamates often ~8–9, literature), implying increased ionization and solubility in basic media. The α-amine will be protonated under acidic conditions, further enhancing water solubility.
The thioether of the methionyl side chain imparts moderate lipophilicity relative to other polar amino-acid derivatives but does not dominate partitioning; overall logP is expected to be low to modest (qualitative literature expectation for amino-acid hydroxamates).
Always consult the specific CoA/SDS for authoritative physical constants before process design.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grade/purity in practice (general guidance)
For building-blocks like amino-acid hydroxamates, grades may emphasize assay purity (by HPLC or qNMR), low inorganic residue (sulfated ash), and control of residual solvents. If HPLC grade is stated, it typically refers to low UV-absorbing impurities suitable for analytical or bioconjugation workflows.
If a stabilizer is listed on the CoA (none specified here), understand its impact on downstream chemistry (e.g., trace acid/base, metal chelators). Hydroxamate-containing materials seldom require stabilizers, but antioxidants may be used to protect the thioether in some lots; validate compatibility with your process.
Verification and documentation
Request and review the CoA and Specification Sheet for: identity (1H/13C NMR, HRMS), chiral purity (ee/er via chiral HPLC), assay (%), water content (KF), and specific limits relevant to your application (e.g., heavy metals, residual solvents).
If using in metal-mediated assays, consider sourcing or specifying a lot with documented low metal content and verify via ICP-MS as needed.
Lot-to-lot control tips
Record appearance, HPLC profile, and optical rotation (if provided) on receipt. Establish internal acceptance criteria for critical reactions to manage variability.
Reaction and Applications
N-Hydroxy-L-methioninamide unites an α-amine, a hydroxamate (–CONHOH), and a thioether, enabling diverse reactivity and utility.
Metal chelation and coordination: Hydroxamates bind hard metal ions (e.g., Fe3+) via O,O- or N,O-chelation; useful for model coordination studies, affinity resins, and metal sequestration experiments. The L-stereocenter may bias complex geometry in chiral environments.
Acyl-transfer chemistry: Hydroxamates can undergo O-acylation and N→O acyl shifts; useful in peptide coupling methodologies and in forming activated intermediates. They also participate in the Lossen-type rearrangements when suitably activated (general hydroxamate chemistry).
Selective oxidation studies: The methionine thioether can be oxidized to sulfoxide/sulfone (e.g., with mCPBA or H2O2 under controlled conditions) to modulate polarity, coordination, or to probe oxidation susceptibility.
Conjugation/derivatization: The α-amine allows standard protecting-group strategies (Boc/Fmoc) and downstream amide formation to craft probes or immobilized ligands. Hydroxamate O-alkylation/acylation provides handles for pro-ligand generation.
Practical tips
Protect from strong oxidants to avoid unintended thioether oxidation.
Hydroxamates can chelate trace metals and attenuate activity of metal catalysts (Pd, Cu, Fe). Add metal scavengers post-catalysis or pre-treat reagents/solvents if catalytic activity is critical.
Maintain controlled pH during aqueous operations: protonation state of the α-amine and N–OH group strongly affects solubility, reactivity, and partitioning.
Reaction Conditions
Representative conditions below are general literature guidance for the functional groups present; they are not item-specific specifications.
O-Acylation of hydroxamate
Solvent: Anhydrous DCM, DMF, or MeCN. Base: DIPEA or pyridine. Reagents: acyl chlorides or anhydrides (1.1–1.5 eq). Temperature: 0–25°C. Time: 0.5–4 h. Monitor to minimize N-acylation; prefer mild bases and low temperatures.
N→O acyl transfer and Lossen-type sequences
Activate O-acyl hydroxamate with e.g., p-nitrophenyl chloroformate or CDI; heat gently (25–60°C) in aprotic solvent. Traps: alcohols/amines as desired. Use inert atmosphere to avoid side oxidations of the thioether.
Thioether oxidation (selective)
To sulfoxide: H2O2 (30%) in MeOH/H2O with catalytic tungstate at 0–5°C; or mCPBA (1.05 eq) in DCM at 0°C to rt. To sulfone: increase oxidant equivalents/temperature. Monitor by LC-MS; avoid over-oxidation that may affect the hydroxamate.
Amine protection (Boc/Fmoc)
Boc2O (1.1–1.5 eq), base (NaHCO3/DIPEA), solvent (dioxane/water or MeCN), 0–25°C. For Fmoc: Fmoc-Cl in aqueous base (Na2CO3) with dioxane co-solvent, 0–25°C.
Coupling to carboxylic acids (amide formation at α-amine)
Reagents: HATU/HBTU/EDC·HCl with HOAt/HOBt alternatives. Solvent: DMF/MeCN. Base: DIPEA. 0–25°C, 1–12 h. Consider transient protection of the hydroxamate if competitive acylation is problematic.
Yields will vary with substrate and protection strategy; verify on small scale and confirm integrity of the N–O bond throughout.
Safety and Handling
Item-specific hazard information
GHS classification, Signal Word, H-statements, Pictograms: Not specified for this item; refer to SDS.
General safety considerations for amino-acid hydroxamates (literature/general guidance)
Irritation/sensitization: Hydroxamic acids and hydroxylamine derivatives can be irritants to skin, eyes, and respiratory tract. Avoid inhalation of dusts and contact with skin/eyes.
Metal chelation: Hydroxamates are strong chelators (especially Fe3+/Fe2+); complexation can alter bioavailability of metals and may interfere with metal-catalyzed reactions. Use glass or compatible plastics; minimize contact with reactive metal surfaces when purity is critical.
Oxidation sensitivity: The methionyl thioether can be oxidized to sulfoxide/sulfone by peroxides or strong oxidants. Store away from oxidizing agents. Use fresh, peroxide-free solvents.
PPE and handling
Wear lab coat, safety glasses, and appropriate gloves (nitrile recommended). Handle in a fume hood when weighing powders or preparing solutions.
Avoid generating dust/aerosols. Use dedicated spatulas/scoops to reduce cross-contamination.
First aid (overview; defer to SDS)
Eyes/skin: Rinse with water for ≥15 min; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product SDS for definitive hazard classification and response measures.
Solvent Selection
This compound is a polar, hydrogen-bonding solid with basic (α-amine) and weakly acidic (hydroxamate) sites.
General miscibility/solubility tendencies (literature expectations)
Water: Typically soluble, especially when protonated (acidic media) or deprotonated at N–OH (basic media). Salt formation (e.g., HCl, TFA) often boosts solubility.
Alcohols (MeOH, EtOH): Good solubility; useful for stock solutions and preparative chromatography.
Polar aprotics (DMSO, DMF, NMP): Excellent solubility; common for high-concentration stocks in biochemical assays or coupling reactions.
Moderately polar organics (Acetonitrile, acetone): Variable; may require small amounts of water or base/acid to aid dissolution.
Nonpolar solvents (EtOAc, MTBE, toluene, hexanes): Poor solubility; used mainly for extractions/partitioning or crystallization antisolvents.
Selection tips by use case
Biochemical/chelation assays: Aqueous buffers (pH 6–8) with limited DMSO (≤10% v/v) to aid dissolution while maintaining metal speciation control.
Coupling/derivatization: Anhydrous DMF/DMSO or mixed MeCN with base (DIPEA) to suppress protonation of nucleophilic sites; include molecular sieves if water-sensitive reagents are used.
Purification: Reverse-phase chromatography with water/MeCN or water/MeOH gradients; add 0.1% acid (e.g., formic acid) for peak shape, noting its effect on ionization state.
Practical note
Avoid oxidizing solvents or peroxide-contaminated ethers to protect the methionyl thioether. Degas solvents if metal-catalyzed steps are anticipated (hydroxamate chelation may inhibit catalysts).
Storage and Reconstitution
Item-specific storage and shipping
Storage Conditions: Room temperature (per Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature/practice)
Keep container tightly closed in a dry place. Protect from strong oxidizers and sources of peroxide. For long-term storage, consider an inert atmosphere (nitrogen/argon) and desiccation to protect the thioether from oxidation and to limit hydrolysis of the N–O bond.
If a salt form is provided (not specified here), follow the same guidance and note that hygroscopicity may increase; reseal promptly after use.
Reconstitution
Dissolve in water, buffer (pH 6–8), or DMSO. Gentle warming (≤40°C) and sonication can aid dissolution. Adjust pH to enhance solubility if needed: mild acid to protonate the amine, or mild base for N–OH deprotonation. Avoid strong acids/bases that may cleave the N–O bond.
For sterile applications, filter through 0.22 µm. Prepare single-use aliquots and store refrigerated or frozen if solution stability is a concern; minimize freeze–thaw cycles.
Stability monitoring
Periodically check by HPLC/MS for signs of oxidation (sulfoxide/sulfone formation) or degradation. Use peroxide-free solvents and amber containers if light sensitivity is suspected.
Always defer to the product’s CoA/SDS for definitive storage, stability, and handling instructions.
Research Use Note: For research use only.
Structure and Identity
N-Hydroxy-L-methioninamide is the L-methionine hydroxamate (the carboxamide is N-hydroxylated), combining an L-α-amino acid backbone with a hydroxamic acid motif and a thioether side chain.
Item-specific identifiers (from Product Data)
CAS: 19253-87-3
PubChem CID: 44277995
InChIKey: 131458 (as provided)
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/computed identifiers (for reference; not item specifications)
Typical 2D structure description: an α-carbon stereocenter (L-configuration) bearing an amino group and the methionyl side chain (–CH2–CH2–S–CH3), attached to a terminal hydroxamate carbonyl (–C(=O)–NHOH). Functional groups include a primary amine, a hydroxamic acid (N–OH), an amide carbonyl, and a thioether.
Chirality: L-configuration at the α-carbon (commonly S configuration for L-methionine in CIP terms).
Functional-group synergy: The hydroxamate (bidentate O,O-/N,O-donor) is a known metal-chelating motif; the thioether can be selectively oxidized (sulfoxide/sulfone chemistry); the α-amine can be protected or derivatized using standard peptide chemistry.
Synthetic Utility
Functional-group leverage
Hydroxamate (–CONHOH): Nucleophilic at O under basic conditions; participates in O-acylation and N→O acyl shifts. Serves as a bidentate ligand in metal-mediated transformations and separations.
α-Amine: Amenable to standard protecting groups (Boc/Fmoc/CBz) enabling orthogonal manipulation alongside the hydroxamate. Facilitates amide couplings to extend into peptidomimetic space.
Thioether: Selectively oxidizable (sulfoxide/sulfone) or alkylatable under controlled conditions for probe diversification.
Retrosynthetic roles (literature/general)
Acts as a chiral building block introducing the methionyl motif and a hydroxamate terminus; useful when the hydroxamate is required at the C-terminus of a peptide mimic or as a metal-binding headgroup.
Intermediate for generating O-acyl hydroxamates that can, upon activation, engage in rearrangements (e.g., Lossen-type) toward isocyanate equivalents for further diversification.
Compatibility considerations
Hydroxamate chelation may inhibit transition-metal catalysis (e.g., Pd cross-coupling). Temporarily masking the N–OH (e.g., O-alkyl protection) or adding catalyst excess/ligand tuning can mitigate.
Control pH to balance nucleophilicity vs. stability; avoid strong acids/bases that can lead to hydrolysis or N–O bond cleavage.
Workup/purification
Reverse-phase chromatography (water/MeCN or water/MeOH) with volatile modifiers is typically effective; ion-pairing agents are generally unnecessary and may complicate MS detection.
Target Specificity
Not applicable. This product is a small-molecule research reagent and is not an antibody, enzyme, or affinity reagent with defined biological target specificity in the Product Data. For potential metal-binding preferences or enzyme-interaction studies, refer to the Reaction & Applications and Biological Roles sections (general literature context).
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