L-Alanosine is an antibiotic substance isolated from the fermentation of|Streptomyces alanosinicus|. The first natural product found to have a N-nitrosohydroxylamino group on an aliphatic chain. An experimental insect reproduction inhibitor.
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Application Protocols
Tested applications and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet or internal validation.
General protocols (research use):
Cell-based metabolic modulation:
Prepare sterile 10–100 mM stock in water/buffer, aliquot, store at −20°C.
Treat cells across a concentration range (e.g., 0.1–300 µM as a broad starting window; refine per literature and pilot tests). Include vehicle and rescue controls (e.g., adenine/adenosine) to confirm pathway involvement.
Assess endpoints after 6–72 h depending on assay (viability, metabolite levels by LC-MS, gene expression of purine pathway markers). Adjust timing to minimize confounders.
Enzyme or lysate assays:
Use buffered conditions (e.g., 50 mM HEPES or Tris, pH 7.2–7.5) with defined cofactors. Preincubate compound as required to reach equilibrium.
Quantify effects via coupled spectrophotometric assays or direct LC-MS readouts of pathway intermediates.
Documentation:
Record lot number, stock concentration, exact solvent/buffer composition, pH, and storage history. Include filtration details and number of freeze–thaw cycles.
Biological Roles
Scope note: The following describes literature-reported biochemical roles of L-Alanosine. No medical or clinical claims are made; this product is for research use only.
Literature overview:
L-Alanosine is reported as an amino-acid–derived antimetabolite that interferes with de novo purine biosynthesis, particularly impacting adenine/AMP formation through effects on adenylosuccinate pathway enzymes (literature).
It is used to probe nucleotide metabolism, cellular energy balance, and compensatory salvage pathways. Rescue experiments with exogenous adenine/adenosine are frequently employed to confirm pathway engagement (literature practice).
Experimental implications:
Time- and dose-dependent effects on nucleotide pools can be quantified by LC-MS metabolomics or enzymatic assays.
Cellular context matters: reliance on de novo versus salvage pathways differs across cell types and culture conditions (literature).
Co-factors and media composition (e.g., purine-free vs standard media) strongly influence observed outcomes; document media, serum, and supplementation rigorously.
Off-target considerations:
As with many antimetabolites, high concentrations or prolonged exposure may lead to general cytostatic or cytotoxic effects; controls for pH/osmolality and matched vehicles are essential (general lab guidance).
Buffer Applications
Item-specific buffer recipes are not provided for this product. The guidance below is general for water-soluble, amino-acid–like small molecules.
Stock solution preparation (general):
Target stock: 10–100 mM in water or buffer. If dissolution is slow, adjust to pH ~1–2 with HCl or ~10–11 with NaOH to aid solubilization, then readjust to the desired assay pH (commonly 7.2–7.4). Sterile filter (0.22 µm).
Keep ionic strength moderate (e.g., 1× PBS or 10–50 mM HEPES/Tris) to avoid salting-out.
Working solutions:
Prepare fresh on the day of use or thaw single-use aliquots. Avoid repeated freeze–thaw cycles that can alter concentration and integrity.
Compatibility notes:
Avoid buffers containing reactive carbonyls or strong oxidants. Minimize exposure to light/air if the molecule contains N–O functionalities susceptible to redox reactions (general precaution).
Quality control:
Verify concentration by UV at low wavelengths (e.g., 210–220 nm) or by quantitative NMR/LC-MS (literature practice). Include pH and osmolality checks for cell-based assays.
Green Alternatives
As a solid research reagent (not a bulk process solvent), the main green-chemistry considerations are solvent selection for dissolution, waste minimization, and energy use during storage.
Greener handling choices (general guidance):
Prefer water or aqueous buffers over organic solvents whenever compatible with your assay.
If an organic modifier is necessary for analytics, choose methanol over acetonitrile when feasible, and keep percentages low.
Use ambient-temperature dissolution when possible; avoid heating that could accelerate degradation and increase energy usage.
Right-size your stock concentrations and aliquot volumes to reduce discard/waste from freeze–thaw cycles.
Comparison (general):
Water/buffer: Highest EHS profile, minimal VOCs; may require pH adjustment for full dissolution.
Methanol (LC-MS modifier): Widely available, relatively lower toxicity among common solvents; flammable and VOC-producing; keep minimal.
Acetonitrile (LC-MS modifier): Excellent elution strength but higher environmental burden; reserve for necessary analytical uses only.
Packaging/waste: Consolidate compatible aqueous waste; avoid chlorinated solvents. Rinse vials with minimal volumes. Follow local regulations for disposal of nitrogen/oxygen-containing organics.
Pharmaceutical Uses
This product is supplied for research use only. No medical, diagnostic, or therapeutic applications are stated or implied.
Reference standard for analytical method development and validation (HPLC/UPLC/LC-MS) involving amino-acid–like antimetabolites.
Process development studies in upstream research settings (e.g., stability-indicating methods, stress testing) to understand degradation pathways of similar chemotypes.
Excipient status/pharmacopeial listings: Not specified for this item; refer to CoA/Spec Sheet and relevant compendia if needed.
Manufacturing and handling considerations (research scale):
Ensure traceability with batch-specific CoA and storage at controlled temperatures to maintain integrity.
Implement light/moisture protection as appropriate based on stability studies (not specified here; consult CoA/SDS).
Physical Properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not applicable for decomposition-prone amino-acid–like solids; specific value not specified for this item; refer to CoA/Spec Sheet. (general note)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility:
Item-specific solubility: Not specified for this item; refer to CoA/Spec Sheet.
General (literature): Amino-acid–like zwitterions are typically water soluble and poorly soluble in most nonpolar organic solvents; dissolution often benefits from mild basification (0.1–1.0 M NaOH) or acidification followed by neutralization and sterile filtration.
pKa/logP/refractive index: Not specified for this item; refer to CoA/Spec Sheet. (Any numerical values should be taken from the CoA/SDS or primary literature.)
Hygroscopicity: Not specified for this item; refer to CoA/Spec Sheet. General caution: amino acid analogs can be moisture sensitive and may clump upon exposure to humid air.
UV cutoff/ε: Not specified for this item; refer to CoA/Spec Sheet. General: monitoring at 210–220 nm is common for amino-acid–like compounds (literature).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What to expect on the CoA/Spec Sheet (typical for this compound class; item-specific values not provided here):
Identification by HPLC/UPLC retention time and/or MS.
Purity by HPLC (area %) and/or qNMR.
Water content by Karl Fischer if applicable.
Residual solvents and related substances profiles.
Optical rotation or chiral purity (ee/er) confirming the L-configuration.
Implications for use:
For biochemical assays and cell-based studies, high chemical purity and correct stereochemistry are critical to ensure consistent biological results.
Low UV background and trace-metal content can be important if using spectroscopic readouts or metalloenzyme assays; verify on the CoA if required.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers may influence downstream assays or analytical detection and should be disclosed in methods sections.
Reaction and Applications
Manufacturer Applications: Not specified for this item in the catalog entry.
Research-use note: For research use only (as provided).
Literature context (no clinical claims):
L-Alanosine is described as a purine-biosynthesis antimetabolite used as a biochemical probe to modulate nucleotide metabolism in cells and enzymatic systems (literature). It is typically employed to study de novo adenine/AMP pathways by perturbing enzyme activities within the purine branch (literature).
Practical applications in the lab (general):
Tool compound for metabolic pathway interrogation (e.g., profiling purine pools, isotope-tracer studies, or rescue experiments with exogenous nucleosides).
Positive/negative control in assays evaluating sensitivity to purine-pathway modulation.
Reference material for method development in LC-MS quantification or for validating transport/uptake studies of amino-acid–like molecules.
Practical tips:
Prepare fresh aqueous stocks, filter sterilize (0.22 µm), and aliquot to minimize freeze–thaw.
Control pH carefully; osmolarity and buffer composition can influence cellular responses independently of the compound.
Include vehicle controls that match any pH-adjusting acid/base used during dissolution.
Reaction Conditions
Item-specific reaction conditions are not provided for this product. The following are general laboratory practices for handling amino-acid–like antimetabolites in solution.
Stock preparation:
Dissolve to 10–100 mM in water or suitable buffer. If needed, adjust pH with dilute NaOH/HCl for dissolution, then readjust to working pH. Filter through 0.22 µm for sterility and clarity.
Stability considerations (general):
Aqueous stability can depend on pH and temperature; store cold and protected from light when possible. Avoid extended exposure to strong acids/bases, oxidants, or reductants that may alter N–O functionalities.
Analytical methods (literature practice):
LC-MS with aqueous mobile phases (e.g., water + 0.1% formic acid) and methanol/acetonitrile gradients; detection at 210–220 nm if using UV.
qNMR in D2O or DMSO-d6 for purity/concentration checks, with attention to exchangeable protons.
Assay setup (cell/enzyme studies):
Pre-equilibrate media/buffers to 37°C for cell assays; verify pH after addition of stock. Include vehicle-only controls matching any acid/base used during dissolution.
Titrate concentration ranges across several logs to establish potency windows; monitor general cytotoxicity separately from pathway-specific readouts.
Safety and Handling
GHS information (item-specific):
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-codes): Not specified for this item; refer to SDS.
Pictograms and classification: Not specified for this item; refer to SDS.
General laboratory precautions (good practice):
Wear appropriate PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Work in a chemical fume hood when handling powders or preparing solutions.
Avoid generating dust/aerosols; use micro-spatulas and weigh boats, and cap vials promptly.
Prevent contact with skin, eyes, and clothing; wash thoroughly after handling.
Incompatibilities (general): Strong oxidizers/bases/acids may degrade amino-acid–like antimetabolites; avoid prolonged exposure to elevated temperature and light. Use aqueous buffers within their compatible pH range.
First-aid overview (summarized; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/accidental release: Avoid dust; collect with dampened absorbent; dispose according to institutional and local regulations.
Fire-fighting: Use water spray, CO2, dry chemical, or foam as appropriate for surrounding materials; thermal decomposition may produce nitrogen/oxide-containing gases (general). Always consult the SDS for authoritative data.
Solvent Selection
This product is a small, polar amino-acid–like compound. Item-specific solubility data are not provided; verify using the CoA/SDS.
General dissolution guidance (literature/practice):
Water and aqueous buffers (e.g., PBS, HEPES, Tris) are typically preferred. Adjust pH to improve solubility: dissolve first in a small volume of 0.1–1.0 M NaOH or HCl, then back-titrate to the target pH (7.2–7.4 for many biological assays) and sterile filter (0.22 µm).
Poorly soluble in nonpolar solvents; limited solubility in alcohols. Avoid strong organic solvents in live-cell assays.
Polarity and miscibility (general): Highly polar/zwitterionic; miscible with water when properly ionized; essentially immiscible with hydrophobic media.
Choosing among alternatives:
For in vitro enzyme or cell assays: aqueous buffers at physiological ionic strength are ideal.
For analytical sample prep: water with a small percentage of acetonitrile or methanol plus 0.1% formic acid can aid LC-MS compatibility (literature practice).
Storage and Reconstitution
Storage conditions (item-specific): Store at -20°C (as provided). Protect from moisture. Keep container tightly closed.
Shipping (item-specific): Shipped in an ice chest with ice pads (as provided) to maintain cold chain.
Reconstitution (general guidance; item-specific specs not provided):
Bring vial to room temperature in a desiccator before opening to prevent condensation.
Prepare aqueous or buffer stocks (e.g., 10–100 mM). If needed, adjust pH for dissolution, then neutralize to working pH. Sterile filter (0.22 µm).
Aliquot into single-use portions to avoid repeated freeze–thaw cycles.
Stability after reconstitution (item-specific not provided): Not specified for this item; refer to CoA/Spec Sheet. As general practice, store aliquots at −20°C or below and use thawed solutions promptly (same day) unless stability has been verified.
In-use precautions:
Avoid prolonged exposure to light and elevated temperature.
Track the number of freeze–thaw events; discard aliquots showing precipitation, discoloration, or unexpected HPLC/LC-MS profiles.
Structure and Identity
Item-specific identifiers from Product Data:
CAS: 5854-93-3
CID: 135409347
InChIKey: 456408 (as provided; note this does not follow the typical 27-character InChIKey format)
Product Name: L-Alanosine
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.
Structural features (general, literature):
L-Alanosine is reported in the literature as an amino-acid–like antimetabolite structurally related to L-alanine, containing an additional N–O functionality on the side chain (literature). It is typically represented as a small, polar, zwitterionic molecule at neutral pH with an α-amino and α-carboxyl group (literature).
Stereochemistry: the “L-” prefix denotes the L-configuration at the α-carbon (literature).
2D structure description (general, literature):
A three-carbon backbone with an α-amino and α-carboxylate moiety (as in canonical amino acids), and a modified β-substituent bearing an N–O functionality responsible for antimetabolite activity (literature).
Synthetic Utility
Primary value: L-Alanosine is principally used as a biochemical tool compound rather than as a general synthetic building block.
Functional groups (general, literature):
Contains α-amino and α-carboxyl functionalities typical of amino acids, enabling salt formation and amide coupling after protection (literature).
Side-chain N–O functionality may be sensitive to reductants/oxidants; protective strategies may be required if derivatization is attempted (general consideration).
Potential transformations (literature/general):
Protection/deprotection: Boc/CBz/Fmoc on the α-amino; esterification of the carboxyl group for prodrug or analog synthesis.
Peptidomimetic incorporation: As a nonproteinogenic residue to probe enzyme/substrate specificity, with careful optimization of coupling conditions.
Caveats:
Stereochemical integrity at the α-carbon must be preserved; avoid racemizing conditions (strong base, elevated temperature, long reaction times).
Item-specific reactivity and stability are not provided; plan small-scale trials and analytical monitoring (HPLC, LC-MS).
Target Specificity
Item-specific biological target details are not provided in the Product Data.
Literature context (no medical claims): L-Alanosine is commonly used to modulate de novo purine biosynthesis, affecting enzymes within the adenylosuccinate/AMP branch (literature). Exact binding targets, Ki/IC50 values, and selectivity profiles should be obtained from primary literature and validated experimentally for each system.
For assay documentation: Cite batch, concentration, exposure time, media composition, and any rescue reagents used (e.g., adenine/adenosine), as these define the functional specificity observed in your model.
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