Pimeloyl-CoA lithium , CAS No.P1439846

CAS: P1439846 Cat. No.: P1439846 Formula: C₂₈H₄₁Li₅N₇O₁₉P₃S Molecular Weight: 939.35

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Pimeloyl-CoA lithium is a biotin precursor of Escherichia coli. Pimeloyl-CoA lithium can be used for the research of the pathway of de novo biotin biosynthesis in Escherichia coli.

Specifications

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

939.35

Application Protocols

No supplier‑validated protocols are provided for this specific item. The following is a general example protocol for an enzymatic assay using an acyl‑CoA substrate (literature‑style guidance; adapt as needed):

Example: Measuring activity of a pimeloyl‑CoA‑processing enzyme

• Prepare buffer: 50 mM HEPES, pH 7.5, 100 mM NaCl, 5 mM MgCl2 (if ATP‑dependent), 1 mM DTT (omit if reductant interferes).
• Prepare fresh substrate: Dissolve pimeloyl‑CoA lithium in ice‑cold buffer to 1–5 mM; aliquot and keep on ice.
• Reaction mix (final): 50 mM HEPES pH 7.5, enzyme at 0.05–2 µM, pimeloyl‑CoA 5–200 µM, required cofactors (e.g., 200 µM FAD or 0.5 mM NAD+), total volume 100–500 µL.
• Incubate at 25–30 °C; take time points at defined intervals.
• Quench: 4 volumes of ice‑cold 80% acetonitrile with 0.1% formic acid; centrifuge to remove protein.
• Analyze supernatant by LC–MS to quantify substrate depletion and product formation; include calibration standards of pimeloyl‑CoA and potential products.

Note: Optimize pH, temperature, and cofactors for the specific enzyme. Implement no‑enzyme and heat‑killed controls to account for nonenzymatic hydrolysis.

Biological Roles

Pimeloyl‑CoA is a biologically relevant acyl‑CoA intermediate linking dicarboxylic acid metabolism to specialized biosynthetic pathways.

Literature-based roles (general):

• Biotin biosynthesis (bacteria): Pimeloyl derivatives serve as early precursors in the biosynthetic pathway to biotin. In certain bacteria, the enzyme BioW (pimeloyl‑CoA synthetase) activates pimelic acid to pimeloyl‑CoA, which is further processed by enzymes such as BioF/BioA toward the fused heterocycle of biotin.
• Dicarboxylate metabolism: As a C7 dicarboxylic acyl‑CoA, pimeloyl‑CoA can participate in reactions analogous to β‑oxidation or other chain‑processing steps adapted for dicarboxylates, informing studies of chain‑length specificity and enzyme promiscuity.
• Regulatory/metabolic profiling: Acyl‑CoA pools influence cellular metabolism; pimeloyl‑CoA standards enable quantification in targeted metabolomics by LC–MS, supporting investigation of metabolic flux under different nutrient conditions.

Notes:

• Cellular concentrations and enzyme specificities are organism‑dependent; verify the relevant pathway map for the model organism under study.
• CoA thioesters are labile; sample prep for biological extracts should be rapid, cold, and acid‑quenched appropriately to preserve acyl‑CoA integrity (general best practice).

Buffer Applications

This product is not a buffering agent and is not typically used to make buffer systems. For experimental work, prepare pimeloyl‑CoA solutions in a preselected biological buffer suitable for the target enzyme (commonly near‑neutral pH). Refer to Solvent Selection and Reaction & Applications for practical guidance.

Green Alternatives

For biochemical substrates such as pimeloyl‑CoA, “green” considerations focus on minimizing waste, avoiding corrosive pH extremes, and generating material in situ to reduce handling of sensitive reagents.

Options and tradeoffs (general; not item-specific):

• In situ generation vs. isolated reagent:

  • Approach: Use enzymatic formation of pimeloyl‑CoA from pimelic acid, ATP, CoA, and BioW (pimeloyl‑CoA synthetase).
  • Pros: Fewer isolation steps/solvents; generates only stoichiometric inorganic byproducts; continuous regeneration systems can be used.
  • Cons: Requires enzyme production/purchase; assay complexity increases; substrate concentrations may be lower and less defined.

• Aqueous-only workflows:

  • Prefer buffered aqueous media at near‑neutral pH; avoid strong acids/bases that create hazardous neutralization waste and accelerate degradation.

• Process intensification:

  • Miniaturize assays (microplate formats) to reduce reagent consumption and waste.

• Packaging/handling:

  • Use aliquoted, ready-to-dissolve vials to minimize repeated thaw cycles and avoid product loss.

Small comparison (general):

• Preformed pimeloyl‑CoA: maximum control over concentration and immediate activity; generates packaging waste.
• Enzymatically generated pimeloyl‑CoA: reduced solvent footprint and improved atom economy; requires biocatalyst supply and cofactor recycling schemes.

Pharmaceutical Uses

Pimeloyl‑CoA lithium is a biochemical research reagent and is not used as a pharmaceutical ingredient or excipient.

Research/manufacturing context (general):

• Analytical standard: May serve as a reference standard for LC–MS method development in metabolomics of acyl‑CoAs.
• Process enzymology: Useful in screening and characterizing enzymes for biocatalytic routes that manipulate dicarboxylic acyl‑CoAs, aiding precompetitive process development.

No pharmacopeial monograph or excipient status is implied. For research use only (as stated by the supplier).

Physical Properties

Item-specific numerical physico-chemical specifications have not been provided for this product.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point / boiling point: Not applicable/Not typically defined for polyanionic CoA thioesters; Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index, density, pKa, logP: Not specified for this item; refer to CoA/Spec Sheet.

General characteristics (literature/typical for acyl‑CoA thioesters; not item-specific):

• State: Nonvolatile, hygroscopic, highly polar solid.
• Solubility: Readily soluble in water and aqueous buffers; essentially insoluble in most nonpolar organic solvents. Limited solubility may be observed in polar aprotic solvents with added water but hydrolysis risk increases.
• Stability: Thioester bond is susceptible to hydrolysis, especially at high pH and elevated temperature; acidic conditions can also promote degradation of the CoA moiety.
• pH sensitivity: Best handled near neutral pH (≈6.8–8.0) to minimize thioester cleavage (literature guidance).
• Light/oxidation: Sensitive to prolonged light exposure and oxidative conditions; store under inert atmosphere when possible (general practice).

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Context and expectations for acyl‑CoA reagents (general guidance):

• Identity confirmation: Typically by high-resolution MS (m/z for [M−H]−), and 1H/31P NMR or LC–MS retention vs. reference. Absence of free CoA and parent acid (pimelate) is often verified by LC.
• Purity metrics: Suppliers commonly report chromatographic purity (HPLC/UPLC) and assay by UV at 259 nm for the adenosine chromophore. For this item, specific acceptance criteria are Not specified; refer to CoA.
• Counterion: Lithium carboxylate form; counterion identity can influence solubility, pH on dissolution, and enzyme compatibility. If critical, verify counterion content on the CoA/Spec Sheet.
• Stability controls: Low-temperature, desiccated storage to minimize thioester hydrolysis. Some lots may be packaged under inert gas; verify on CoA if needed.

Recommendations:

• Request the lot-specific CoA for exact assay, related substances, water content, and residual solvents (if any). Validate suitability for sensitive enzymology by running a quick LC–MS check for free CoA and pimelate prior to use in kinetic assays.

Reaction and Applications

Pimeloyl‑CoA lithium is a convenient, ready-to-use substrate or reference standard for studying metabolism of dicarboxylic acyl‑CoAs and pathways that generate or consume pimeloyl‑CoA.

Representative applications (literature/general):

• Biotin biosynthesis: Substrate or product standard related to BioW (pimeloyl‑CoA synthetase) and downstream enzymes that channel pimeloyl units toward biotin formation in bacteria.
• Dicarboxylate β‑oxidation/oxidative pathways: Use as substrate in assays with acyl‑CoA dehydrogenases, enoyl‑CoA hydratases, or thiolases that accept dicarboxylic substrates, enabling mechanistic studies and kinetic profiling.
• Enzyme characterization: Determine Km/kcat for enzymes acting on pimeloyl‑CoA; employ LC–MS to quantify product formation (e.g., enoyl‑, hydroxyacyl‑, or shortened acyl‑CoAs).
• Analytical reference: LC–MS standard for targeted metabolomics of acyl‑CoA pools from cells or bacterial cultures.

Practical tips:

• Prepare fresh, neutral pH stock solutions (ice-cold) and aliquot to avoid repeated freeze–thaw.
• Include Mg2+ and ATP only when running ligase/coupled assays; otherwise avoid unnecessary components that may affect stability.
• Monitor integrity by UV (259 nm) and LC–MS; the appearance of free CoA or pimelate indicates hydrolysis.
• Use inert atmosphere for prolonged incubations to minimize oxidative degradation of the CoA moiety.

Reaction Conditions

Typical assay conditions for acyl‑CoA substrates (literature-derived, general guidance; not item-specific):

• Solvent/buffer: 10–100 mM HEPES, Tris, or phosphate buffer, pH 7.0–8.0. Include 1–10 mM MgCl2 if ATP‑dependent enzymes are present.
• Temperature: 20–37 °C depending on enzyme source; lower temperatures enhance thioester stability during long incubations.
• Cofactors: Add FAD, NAD+, or NADH only if required by the enzyme being studied (e.g., acyl‑CoA dehydrogenases). Keep oxygen control for oxidases/dehydrogenases as needed.
• Substrate concentrations: 1–500 µM are common for kinetic studies; adjust to span expected Km.
• Time: Seconds to hours; monitor progress by continuous spectrophotometry (coupled assays) or by time‑course LC–MS/UPLC.
• Quench/extraction: For LC–MS, quench aliquots with ice‑cold acidified acetonitrile/methanol (literature practice) to stop enzymatic activity and preserve acyl‑CoAs, then analyze promptly at low temperatures.
• Controls: Include no‑enzyme, heat‑inactivated enzyme, and free CoA/pimelate controls to assess nonenzymatic hydrolysis.

Expected outcomes: Reaction rates and yields are enzyme‑dependent; consult primary literature for the specific enzyme acting on pimeloyl‑CoA. Always validate stability of the substrate under chosen conditions.

Safety and Handling

Hazard classification for this specific item has not been provided. Always consult the product SDS for authoritative safety information.

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

General laboratory handling guidance for CoA thioesters (literature-based):

• PPE: Use lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a clean area to avoid enzymatic or microbial contamination that can hydrolyze thioesters.
• Avoid: Strong bases, strong acids, and nucleophiles that can accelerate thioester cleavage. Avoid metal contaminants that may catalyze decomposition.
• Incompatibilities: Oxidizing agents; prolonged exposure to moisture and elevated temperatures.
• Hygroscopicity: Keep tightly sealed and desiccated; open only at ambient conditions briefly.
• First aid (general): In case of contact, rinse skin/eyes with water. If inhaled (unlikely, low volatility), move to fresh air. If ingested, rinse mouth and seek medical attention. Follow institutional protocols.
• Waste: Dispose of aqueous solutions and solids according to local regulations for laboratory organic salts/biochemicals.
• Transport/receipt: Shipped cold; inspect for temperature excursions and dryness of desiccant upon receipt.

Defer to SDS for spill response, exposure limits, and detailed toxicological data.

Solvent Selection

This compound is a highly polar, polyanionic biochemical. Solvent choice is driven by stability of the thioester and assay compatibility rather than chromatographic purity alone.

General guidance (literature-based; not item-specific):

• Preferred: Water and aqueous buffers (e.g., 10–100 mM HEPES, Tris, or phosphate, pH 7.0–8.0) to maintain thioester integrity and enzyme compatibility.
• Avoid: Strongly basic solutions (pH > 9), which accelerate thioester hydrolysis; strong acids (< pH 5) can degrade CoA and release pimelic acid.
• Organic solvents: Poor solubility in nonpolar media. If co-solvent is required for a mixture, use minimal volumes of polar miscible solvents (e.g., ≤10% v/v acetonitrile) while monitoring stability.
• Ionic strength: Moderate salt can stabilize proteins in coupled assays; however, high ionic strength may affect enzyme kinetics.

Comparison (general):

• Pimeloyl‑CoA lithium vs sodium/ammonium salts: lithium form may show slightly different dissolution pH and ionic strength contributions; enzyme performance is typically similar but should be empirically verified.
• Acyl‑CoA vs corresponding acid or CoA: acyl‑CoA directly participates in acyl‑transfer/oxidation reactions, whereas pimelic acid requires ATP‑dependent ligation (e.g., by BioW) to form the CoA thioester in situ.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20 °C, desiccated. Shipped in an ice chest with ice pads.
• Container handling: Keep vial tightly closed. Allow to warm briefly in a desiccator before opening to minimize moisture uptake. Reseal promptly; purge headspace with inert gas if available.
• Stability: Thioester moiety is moisture-, pH-, and temperature‑sensitive. Minimize time at room temperature. Protect from light.
• Reconstitution (general guidance for CoA thioesters; not item-specific):
  • Dissolve in ice‑cold water or neutral buffer (e.g., 10–50 mM HEPES/Tris, pH 7.0–8.0).
  • Typical working concentrations: 0.1–10 mM stocks, depending on assay demands.
  • Filter sterilization is usually unnecessary; if required, use low‑binding filters and work rapidly to avoid hydrolysis.
• Aliquoting: Prepare single‑use aliquots; avoid repeated freeze–thaw cycles. Store aliquots at −20 to −80 °C for short‑ to medium‑term use.
• Compatibility: Avoid strong acids/bases and nucleophiles. Check compatibility of reducing agents and metal ions with the intended enzyme and with thioester stability.
• Expiry/open‑vial: For best results, use reconstituted solutions promptly (same day). Refer to CoA/Spec Sheet for any lot‑specific shelf‑life information.
• Research use only: Not for human or animal therapeutic use.

Structure and Identity

Pimeloyl-CoA lithium is the lithium salt of the coenzyme A thioester of pimelic acid (heptanedioic acid), furnishing a dicarboxylic acyl-CoA with one free carboxylate (as lithium carboxylate) and one thioesterified carboxyl group.

• 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.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• CAS: P1439846 (internal catalog identifier provided; not a standard CASRN)
• Structural features (general description):
  • Coenzyme A core: 3′-phosphoadenosine-5′-diphosphate linked to pantetheine.
  • Thioester linkage: The pantetheine terminal thiol is acylated by pimelic acid, yielding pimeloyl–S–CoA.
  • Dicarboxylate acyl chain: Heptanedioyl (C7) with one terminus as a thioester, the distal terminus remaining as a carboxylate present as a lithium salt.
  • Ionic character: Multiple phosphate groups (negatively charged) and a lithium counterion; overall highly polar, polyanionic.
• 2D description in words: Adenosine (purine ribonucleoside) bearing a 3′-phosphate and a 5′-pyrophosphate to pantetheine; the pantetheine thiol forms a thioester to a linear C7 chain ending in a free carboxylate (as Li+ carboxylate). No stereogenic centers beyond those inherent to CoA (D-ribose and pantothenate).

Synthetic Utility

As a highly functionalized biochemical, pimeloyl‑CoA is not a general-purpose building block for small‑molecule synthesis; however, it is valuable in biocatalytic and chemoenzymatic contexts.

Utility (general):

• Acyl transfer chemistry: Enzymes can channel pimeloyl units via thioester activation into C–C bond‑forming steps or ring‑assembly processes (e.g., early stages of biotin biosynthesis).
• Model substrate: Probe substrate scope, chain‑length selectivity, and kinetic parameters of acyl‑CoA‑processing enzymes (synthetases, dehydrogenases, hydratases, thiolases).
• Isotope tracing: Isotopically labeled pimeloyl‑CoA (when available) enables flux analysis in engineered pathways.

Practical notes:

• Avoid nonenzymatic thioester exchange or hydrolysis by maintaining neutral pH and low temperature.
• Quantify and normalize using the adenosine chromophore (A259) and LC–MS to ensure accurate concentrations for kinetic experiments.

Target Specificity

This product is a small‑molecule biochemical (acyl‑CoA thioester) and does not possess target specificity attributes such as antigen, clone, isotype, or species reactivity. For enzyme substrate specificity, refer to Biological Roles and Reaction & Applications.

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is P1439846, the molecular formula is C28H41Li5N7O19P3S, and the molecular weight is 939.35 g/mol.

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.