nocardicin A - Moligand™ , CAS No.39391-39-4

CAS: 39391-39-4 Cat. No.: N612347 Formule: C₂₃H₂₄N₄O₉ Poids moléculaire: 500.46 PubChem CID: 6400657

GRADE & PURITY Moligand™

Synonyms

SCHEMBL1442259 | UNII-R76HLW7Z19 | O-{4-[(1Z)-2-{(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-ylamino}-N-hydroxy-2-oxoethanimidoyl]phenyl}-D-homoserine | AKOS040747216 | Nocardicin A | 1-AZETIDINEACETIC ACID, 3-(((2Z)-2-(4-((3R)-3-AMINO-3-C

Storage

Room temperature

Specifications

Synonymes

SCHEMBL1442259 | UNII-R76HLW7Z19 | O-{4-[(1Z)-2-{(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-ylamino}-N-hydroxy-2-oxoethanimidoyl]phenyl}-D-homoserine | AKOS040747216 | Nocardicin A | 1-AZETIDINEACETIC ACID, 3-(((2Z)-2-(4-((3R)-3-AMINO-3-C

Spécifications et pureté

Moligand™

Conditions de stockage de stockage

Room temperature

Grade

Moligand™

Noms et identifiants

Sourires canoniques

C1C(C(=O)N1C(C2=CC=C(C=C2)O)C(=O)O)NC(=O)C(=NO)C3=CC=C(C=C3)OCCC(C(=O)O)N

IUPAC Name

(2R)-2-amino-4-[4-[(Z)-C-[[(3S)-1-[(R)-carboxy-(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid

InChIKey

CTNZOGJNVIFEBA-UPSUJEDGSA-N

INCHI

1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18-/t16-,17+,19-/m1/s1

Isomères SMILES

C1[C@@H](C(=O)N1[C@H](C2=CC=C(C=C2)O)C(=O)O)NC(=O)/C(=N\O)/C3=CC=C(C=C3)OCC[C@H](C(=O)O)N

PubChem CID

6400657

Poids moléculaire

500.46

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Monobactams N-acyl-alpha amino acids and derivatives Phenylacetamides D-alpha-amino acids Phenoxy compounds Phenol ethers 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Dicarboxylic acids and derivatives Tertiary carboxylic acid amides Ketoximes Secondary carboxylic acid amides Amino acids Azetidines Azacyclic compounds Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-dipeptide - Monobactam - N-acyl-alpha amino acid or derivatives - Alpha-amino acid - Alpha-amino acid or derivatives - D-alpha-amino acid - Phenylacetamide - Phenoxy compound - Phenol ether - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Beta-lactam - Ketoxime - Tertiary carboxylic acid amide - Secondary carboxylic acid amide - Amino acid or derivatives - Azetidine - Carboxamide group - Lactam - Amino acid - Organoheterocyclic compound - Azacycle - Carboxylic acid - Ether - Organic oxygen compound - Primary aliphatic amine - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxide - Organonitrogen compound - Organooxygen compound - Amine - Organopnictogen compound - Primary amine - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: Monobactams

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

Propriétés chimiques et physiques

• Poids moléculaire: 500.500 g/mol
• XLogP3: -1.100
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 500.154 Da
• Monoisotopic Mass: 500.154 Da
• Topological Polar Surface Area: 212.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 851.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, validated application protocols are provided in the Product Data. The following are general research-use procedures for small-molecule probes like nocardicin A (literature-informed; adapt as needed):

• Preparation of DMSO stock:

  • Weigh compound quickly in a low-humidity environment.
  • Dissolve in anhydrous DMSO to 10–50 mM. Vortex gently and, if needed, sonicate briefly. Filter through 0.2 µm PTFE to remove particulates.
  • Aliquot into inert vials; minimize headspace and light exposure.

• Enzyme inhibition assay (PBPs/β‑lactamases):

  • Buffer: 25–50 mM HEPES or MOPS, 100 mM NaCl, pH 7.2; 0.01% Tween‑20; 1–2% DMSO final.
  • Incubate enzyme with serial dilutions of compound (e.g., 0.03–100 µM) at 25–37 °C for defined preincubation times (time-dependent covalent inhibition).
  • Readout: activity-based probe competition, nitrocefin turnover, or LC–MS detection of acyl-enzyme adducts. Fit kobs vs [I] to extract kinact and KI when applicable.

• Sample quench for LC–MS:

  • Quench aliquots into 3–5 volumes of 0.1% formic acid in MeCN/H2O (1:1) and analyze within 1 h.

These protocols are starting points only; optimize concentrations, times, and temperatures for your target system.

Biological Roles

Literature (general, non-clinical):

• Origin: Nocardicin A is a natural β‑lactam produced by actinomycetes (e.g., Nocardia/Actinosynnema species). It is structurally distinct from penams/cephems as a monocyclic 2‑azetidinone linked to peptide-derived aromatics.
• Biochemical mechanism: Covalent, mechanism-based acylation of active-site serine residues in PBPs (DD-transpeptidases), interrupting peptidoglycan cross-linking pathways. It is also used to interrogate serine β‑lactamase catalysis and resistance spectra because of its unique ring electronics and side-chain environment.
• Selectivity themes: Monocyclic β‑lactams often display altered spectra of enzyme reactivity relative to penicillins/cephalosporins; nocardicin A’s aryl/phenolic substituents modulate binding in PBP and β‑lactamase active sites, impacting acylation and deacylation kinetics.
• Biosynthesis: Arises from a nonribosomal peptide synthetase (NRPS)-like pathway assembling hydroxyphenylglycine units and forming the β‑lactam ring enzymatically; variants (e.g., nocardicin B) differ in oxidation state/functionalization.
• Research relevance: Serves as a benchmark natural product for structure–activity studies, enzyme kinetics (k2/Ks), crystallography of acyl-enzyme complexes, and as a scaffold for probe development.

Note: The above describes biological roles in fundamental research. This product is supplied strictly for research use only as stated in the Product Data.

Buffer Applications

Nocardicin A is not a buffering agent. However, buffer selection is critical for its stability and for enzymology assays in which it is used.

• Practical buffer guidance (general, not item-specific):
  • Assay pH: near-neutral conditions (pH 6.5–7.5) balance enzyme activity and β‑lactam stability. Avoid prolonged exposure above pH 8.
  • Common systems: HEPES, MOPS, or phosphate at 25–50 mM ionic strength. Include NaCl (50–150 mM) to reduce nonspecific adsorption.
  • Nucleophile content: minimize primary amines (e.g., Tris) when possible to reduce non-enzymatic β‑lactam opening; if Tris is required, validate stability empirically and shorten incubation times.
  • Additives: 0.01–0.05% nonionic surfactant (Tween‑20, Pluronic F‑68) can reduce surface losses in microplates; include 1–2% DMSO from stock to maintain solubility.
  • Quench strategies: for kinetic sampling, quench with acidified MeCN or 0.1% formic acid in MeOH/H2O prior to LC–MS.

These are general guidelines; optimize conditions for your enzyme/assay system and confirm with stability time courses.

Green Alternatives

For nocardicin A itself, greener considerations focus on solvent and processing choices rather than replacing the active scaffold.

• Greener handling strategies (general):

  • Stock solutions: Use anhydrous DMSO at minimal volumes; dispense via acoustic or pin tools to reduce solvent usage.
  • Analytics/purification: Favor water/MeCN over halogenated solvents; optimize gradients to shorten run times and reduce waste.
  • Reactions/derivatizations: Employ water-miscible, lower-toxicity solvents (EtOAc, MeCN, 2‑MeTHF) where compatible; avoid DMF/NMP unless necessary.

• Comparison of solvent choices (literature-informed):

  • DMSO vs DMF: DMSO typically offers lower toxicity and better biocompatibility for screening. DMF may enhance solubility slightly but has worse EHS profile.
  • 2‑MeTHF/CPME: Greener for extractions, but limited solubility for highly polar β‑lactams; useful in workup, not for stock solutions.
  • Aqueous buffers: Preferred for assays; keep pH near neutral and minimize amines to limit β‑lactam hydrolysis.

• Sourcing considerations:

  • Natural product isolation vs total/semi-synthesis: semi-synthetic routes may reduce reliance on large-scale fermentation/extraction, but trade-offs include reagent footprints. Select route based on availability, step economy, and waste minimization.

Trade-offs: Maximizing aqueous usage can accelerate hydrolysis; balance greener media with the need to preserve β‑lactam integrity by using short contact times and lower temperatures.

Pharmaceutical Uses

This product is provided for research use only. No medical or clinical claims are made.

• Formulation/analytical roles in a pharmaceutical R&D context (general, literature-based):

  • Reference standard: used as a natural-product comparator in β‑lactam analytical methods (LC–MS, HPLC) and impurity profiling.
  • Mechanistic control: benchmark inhibitor/substrate in enzymology panels profiling PBPs and serine β‑lactamases during discovery campaigns.
  • SAR starting point: scaffold for medicinal chemistry exploration of monocyclic β‑lactams (derivatization at phenolic/carboxyl positions). Any analog development remains preclinical/research.

• Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet and relevant compendia.

• Excipients/stabilizers: Not specified for this item. In general, aqueous formulations of β‑lactams may leverage buffers near neutral pH and minimal nucleophiles; however, such formulations are for in vitro research only.

All uses should remain within laboratory research, method development, or discovery screening settings.

Physical Properties

Item-specific physico-chemical specifications (BP/MP, density, solubility, pKa, logP, refractive index, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for nocardicin A (non-binding, for planning only):

• Physical state: typically an off-white to light-colored solid as the free acid or a salt; strongly hydrogen-bonding and hygroscopic tendencies are common for peptide-like β‑lactams.
• Solubility profile: often sparingly soluble in neutral water as the free acid, but readily soluble in polar aprotic solvents (DMSO, DMF) and in aqueous buffers at basic pH via carboxylate deprotonation; salts (e.g., sodium) display improved aqueous solubility. Actual solubility must be validated with the supplied lot.
• Acid-base behavior: presence of carboxylic acid(s) and phenolic OH groups; apparent pKa values commonly in the ranges of ~2–5 (carboxyl) and ~8–10 (phenolic), enabling pH-tunable solubility. Verify experimentally for the specific material.
• Stability considerations: β‑lactam ring is strain-activated—susceptible to nucleophilic ring opening (especially under strong base or with amines), and to hydrolysis in aqueous media at elevated temperature or extreme pH.

Important: Do not treat the above as specifications. When planning analytics (HPLC/LC–MS, qNMR), establish empirical conditions (mobile phase pH, ion-pairing, column chemistry) based on small-scale solubility screens and the item’s CoA.

Quality and Grades

• Item-specific grade (from Product Data): Moligand™.
• Interpretation: Moligand™ indicates the material is curated for small‑molecule screening and discovery workflows (e.g., target engagement, biochemical assays, mechanistic probes). This typically emphasizes:
  • Identity confirmation (e.g., LC–MS/HRMS, NMR) suitable for hit-finding/medchem.
  • Purity adequate for research screening. Exact assay/purity thresholds are Not specified for this item; refer to CoA/Spec Sheet.
  • Form factor compatible with compound management (mass, vialing, storage conditions).
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. For β‑lactams, absence/presence of stabilizers (e.g., base, salts, antioxidants) can influence shelf-life and chromatographic background.
• What this means for your workflow:
  • Analytical use: Expect LC–MS tractability; verify UV profile and ionization mode (ESI±) empirically due to multiple phenolic/acidic sites.
  • Screening: Dissolve in dry DMSO to prepare high-concentration stocks (e.g., 10–50 mM), then dilute into assay buffer immediately before use to limit hydrolysis.
  • Documentation: For critical work (e.g., kinetics, standards), capture lot-specific certificate data (purity method, residual solvents, water content) directly from the CoA.

Reaction and Applications

Research use contexts for nocardicin A (expanding on its role as a mechanistic probe; literature-based, not item-specific):

• Enzymology and mechanism:

  • Probe for penicillin-binding proteins (PBPs) and related DD-transpeptidases in peptidoglycan biosynthesis. The β‑lactam ring undergoes acylation at the active-site serine, enabling kinetic and structural studies (e.g., time-dependent inhibition, acyl-enzyme intermediate capture).
  • Tool for serine β‑lactamases: used to study hydrolysis pathways, turnover kinetics, and resistance determinants due to its monocyclic architecture distinct from penams/cephems.

• Chemical biology:

  • Scaffold for derivatization with reporter tags (fluorophores, biotin) via phenolic or carboxyl functionalities to generate activity-based probes, provided derivatization preserves β‑lactam integrity.

• Analytical applications:

  • Reference material in LC–MS method development for β‑lactam detection/quantitation in natural product extracts or biosynthetic studies.

• Practical tips:

  • Maintain low nucleophile background in buffers (avoid high amine concentrations) to minimize non-specific ring opening.
  • Use rapid-mixing kinetics or stopped-flow to characterize acylation rates; quench with acidic solvents for LC–MS capture of intermediates.
  • For immobilization or tagging, prefer mild coupling (e.g., EDC/NHS at pH 5.5–6.0) to derivatize carboxyl groups while minimizing β‑lactam degradation.

Reaction Conditions

General reaction and handling conditions for derivatizing or using nocardicin A (literature-informed; not item-specific):

• Amide coupling at carboxyl group(s):

  • Reagents: EDC·HCl (1.1–1.5 eq) + NHS (1.1–1.5 eq) in DMF/H2O or MeCN/H2O, pH 5.5–6.0 (MES buffer) to limit β‑lactam hydrolysis.
  • Temperature/time: 0–25 °C, 0.5–2 h activation; immediate coupling to amine partners (≤4 h total contact).

• Phenolic O‑alkylation/esterification:

  • Mild carbonate formation with p‑nitrophenyl chloroformate or DSC at 0–5 °C in dry MeCN/DMF, pyridine equivalents minimized; then react with nucleophile at ≤25 °C.

• Protection strategies:

  • Temporary silylation of phenols (TBDMS/TBS) under mild conditions; avoid strong base.
  • Carboxyl masking as methyl/benzyl esters using neutral coupling (DCC/DMAP alternatives kept minimal) rather than direct acidic alcoholysis.

• Stability controls:

  • Keep pH near neutral; avoid extended exposure to pH >8.
  • Include scavengers (e.g., minimal base, anhydrous conditions) to reduce unintended ring opening.

• Analytical monitoring:

  • LC–MS (ESI−/ESI+) with acidic aqueous mobile phase (0.05–0.1% formic acid) and MeCN gradient; monitor exact mass of parent and ring-opened species.

Yields and exact kinetics depend strongly on substitution pattern and conditions; confirm with small-scale trials and orthogonal analytics (qNMR, HRMS).

Safety and Handling

• Product Data hazard fields (GHS class, signal word, H‑statements, pictograms): Not specified for this item; refer to SDS.
• General laboratory safety guidance for β‑lactam natural products (literature; not item-specific):
  • Sensitization risk: β‑lactams may act as skin/respiratory sensitizers. Avoid inhalation and skin contact; handle as a potential allergen.
  • Irritation: phenolic/acidic functionalities may cause eye/skin irritation.
  • PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize aerosol/dust exposure.
  • First aid (overview; defer to SDS): rinse skin/eyes with water for ≥15 minutes upon contact; move to fresh air if inhaled; seek medical attention if symptoms persist. If ingested, rinse mouth; do not induce vomiting unless directed by medical personnel.
  • Incompatibilities: strong bases and nucleophiles (risk of β‑lactam ring opening), strong acids or bases at elevated temperature (hydrolysis), oxidants (phenolic oxidation). Avoid prolonged exposure to moisture and heat.
  • Handling tips: prepare fresh solutions; minimize residence time at high pH; use dry, oxygen- and light-limited conditions for stock solutions where feasible. Filter using low-binding membranes (PTFE or PVDF) to limit adsorption.

Always consult the official SDS for authoritative hazard classification and response procedures before use.

Solvent Selection

Nocardicin A is a polar, hydrogen-bond-rich β‑lactam with acidic/phenolic groups; solvent choice strongly impacts stability and assay performance.

• Practical solvent guidance (general, not item-specific):

  • Stock preparation: dry DMSO is commonly preferred for discovery workflows; it solubilizes polyfunctional natural products while limiting immediate hydrolysis. DMF is an alternative but less favored for bioassays.
  • Aqueous compatibility: free acid forms are more soluble at basic pH (≥8) due to carboxylate formation; salts show improved solubility in neutral buffers. Keep exposure to high pH brief to preserve the β‑lactam.
  • Volatile media: MeCN/H2O (LC–MS), MeOH (limited) can be used for analytics; avoid prolonged storage in alcoholic solvents (risk of transesterification/solvolysis under basic conditions).
  • Avoid: strong nucleophiles (amines, thiols) or strongly basic media for extended times.

• Miscibility/polarity (literature expectations):

  • Highly polar and hydrophilic in deprotonated forms; moderate solubility in neutral water; good solubility in polar aprotics.

• When to choose alternatives:

  • For long incubations, consider buffered aqueous media near neutral pH with minimal nucleophiles, spiked from a fresh DMSO stock.
  • For purification, use reversed-phase chromatography (C18) with acidic mobile phases to maintain integrity; avoid high-pH columns that can induce ring opening.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Practical guidance (general, not item-specific):

• Solid material:

  • Store tightly capped in a desiccator, protected from light. Although room temperature is indicated, many users prefer 2–8 °C for long-term retention of β‑lactam integrity—follow your QA practices and the CoA.
  • Allow vial to equilibrate to room temperature before opening to prevent moisture condensation.

• Reconstitution:

  • Prepare concentrated stocks in anhydrous DMSO (e.g., 10–50 mM). Mix gently until fully dissolved.
  • For aqueous use, dilute the DMSO stock into buffer immediately before the experiment. Keep pH near neutral and minimize exposure time.

• Solution stability:

  • Working solutions are best prepared fresh. For short-term storage, aliquot and freeze at −20 to −80 °C, protected from light. Avoid repeated freeze–thaw cycles; use single‑use aliquots.
  • Monitor integrity by LC–MS/HPLC over time to detect any β‑lactam ring opening.

• Research use note: For research use only (per Product Data). Always defer to the item’s CoA/SDS for lot-specific handling and stability information.

Structure and Identity

Nocardicin A is a naturally occurring, monocyclic β‑lactam (monobactam-like) peptide-derived scaffold used widely as a mechanistic probe for cell-wall biosynthesis enzymes.

• Item-specific identifiers (from Product Data):

  • SKU: N612347
  • Product name: nocardicin A
  • CAS: 39391-39-4
  • InChIKey: 53266 (as provided)
  • Grade: Moligand™
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/structural notes (general chemistry, not item-specific):

  • Typical molecular formula reported in literature: approximately C26H27N3O10 (monocyclic β‑lactam natural product).
  • Core structural features: a strained 2‑azetidinone (β‑lactam) ring; a dipeptidic side chain bearing phenolic aryl groups (p‑/o‑hydroxyphenylglycine–like motifs); one or more carboxylate/phenolic functionalities enabling salt formation and H‑bonding.
  • Stereochemistry: multiple defined stereocenters across the β‑lactam and amino acid–derived fragments; absolute configuration depends on the natural product and must be confirmed by primary literature/CoA.
  • 2D description: a four‑membered β‑lactam ring attached at C3/C4 to a peptidic appendage terminating in aromatic phenyl rings with phenolic OH groups; pendant carboxylate proximal to the amide region; overall polar, H‑bond rich scaffold.

• Use note: For research use only (per Product Data). Refer to the item’s CoA for definitive structural identifiers specific to this lot.

Synthetic Utility

While nocardicin A is primarily a biological probe, it also serves as a complex synthetic scaffold for methodology and SAR studies (literature-based, not item-specific):

• Functional group handles:

  • β‑Lactam ring: electrophilic, susceptible to nucleophilic opening; careful conditions enable selective modifications or mechanistic studies of ring reactivity.
  • Carboxyl group(s): amenable to activation (e.g., EDC/NHS, CDI) for amide coupling to reporter tags or carrier polymers under mildly acidic conditions to protect the β‑lactam.
  • Phenolic OH: allows etherification/esterification (e.g., carbonate, carbamate, sulfonate) to tune polarity and target engagement.

• Strategic applications:

  • Activity-based probe construction by installing fluorophores/affinity tags while retaining β‑lactam acylation capability.
  • Late-stage diversification: chemoselective acylations or protective group strategies to explore binding pocket interactions in PBPs/β‑lactamases.
  • Chiral information: inherent stereocenters offer a platform to study stereochemical effects on enzyme acylation/deacylation.

• Cautions:

  • Strong base and nucleophiles can inactivate the scaffold; use buffered, mildly acidic to neutral conditions and short reaction times.
  • Monitor reactions by LC–MS to detect ring-opened byproducts.

Overall, nocardicin A’s densely functionalized architecture enables targeted derivatization for chemical biology without extensive de novo synthesis.

Target Specificity

This section is adapted for small molecules. Nocardicin A is not an antibody or protein reagent; item-specific epitope/clone/isotype data do not apply.

Literature-based biochemical target context (not item-specific):

• Primary target class: penicillin-binding proteins (PBPs; DD-transpeptidases) involved in bacterial peptidoglycan cross-linking.
• Mechanism: covalent, time-dependent acylation of the catalytic serine by the β‑lactam, forming an acyl-enzyme intermediate whose stability and breakdown kinetics define apparent potency.
• Off-target/related enzymes: serine β‑lactamases (class A/C/D) can bind/acylate and hydrolyze monocyclic β‑lactams with enzyme-dependent efficiency; nocardicin A is used to profile these interactions.
• Selectivity drivers: side-chain phenolic/aromatic motifs contribute to active-site recognition, modulating acylation (k2/Ks) and deacylation rates.

For experimental work, determine target engagement using biochemical assays (e.g., nitrocefin competition, fluorescent PBPs, MS-based acyl-enzyme detection) under your specific buffer and temperature conditions.

Foire aux questions

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 39391-39-4, the molecular formula is C23H24N4O9, and the molecular weight is 500.46 g/mol. InChIKey CTNZOGJNVIFEBA-UPSUJEDGSA-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.