GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
External Descriptors
Pure sugars
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
179.170 g/mol
XLogP3
-2.900
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
1
Exact Mass
179.079 Da
Monoisotopic Mass
179.079 Da
Topological Polar Surface Area
113.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
155.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
Undefined Atom Stereocenter Count
1
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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Application Protocols
From Product Data (item-specific):
Tested applications, recommended dilutions, positive controls: Not specified for this item.
General research protocols (guidance; not item-specific):
Enzyme inhibition assay (glycosidase panel):
Prepare a 10–100 mM aqueous stock of nojirimycin (filter-sterilize if needed).
Dilute into assay buffer (e.g., 50 mM sodium acetate, pH 5.5 for many α-glucosidases) maintaining ≤2% of stock solvent.
Incubate enzyme with serial dilutions (e.g., 0.1–1000 µM) for 10–15 min at assay temperature.
Initiate with fluorogenic or chromogenic substrate; monitor initial rates; fit to a competitive model to derive Ki.
NMR sample prep:
Dissolve 5–20 mg in 0.6 mL D2O; optional 1–2 drops DCl to reduce exchange broadening.
Acquire 1H, 13C, COSY, HSQC to confirm ring conformation and substitution.
Derivatization for LC–UV quantitation:
React aliquots with benzoyl chloride or dansyl chloride under basic aqueous conditions.
Quench, extract if needed, and analyze by RP-HPLC with UV detection; calibrate versus derivatized standards.
These are example workflows only; optimize conditions for your specific enzyme system or analytical platform.
Biological Roles
Scope note: The following summarizes literature knowledge for research context only. This product is supplied strictly for laboratory research use; no clinical/therapeutic claims are made.
Literature/general (not item-specific):
Mechanistic role: Nojirimycin is a canonical iminosugar that mimics the oxocarbenium-like transition state of glycosidic bond cleavage. The endocyclic nitrogen, when protonated, resembles the charge distribution of the enzymatic TS, enabling tight, competitive binding to retaining glycosidases.
Enzyme classes probed: Commonly studied with α/β-glucosidases and mannosidases; selectivity can be modulated through N-alkylation and O-substitutions of the nojirimycin core.
Biochemical utilities: Employed as a reference inhibitor in assays quantifying glycosidase activity, in mechanistic enzymology (kcat/Km shifts), and in structural biology (cocrystal formation with active sites to map binding interactions).
Cellular considerations: Due to high polarity, the free base typically exhibits limited passive permeability; uptake in cells can be enhanced via transporter mediation or by converting to prodrug-like derivatives (research probes only).
Metabolism and fate: Expected to exist predominantly as a protonated species at physiological pH; may undergo renal clearance in vivo (not relevant to lab use) and minimal phase I oxidation due to polyol nature.
Practical notes for researchers:
For enzyme assays, maintain ionic strength and pH carefully; small pH shifts around the conjugate-acid pKa (literature ~7–8 range) influence binding and observed Ki.
Report and control the salt form when comparing activity data across labs, as protonation state affects apparent potency and solubility.
Buffer Applications
Applicability: Nojirimycin is not used as a conventional buffering agent. While it contains a basic nitrogen that can be protonated, dedicated buffers (HEPES, MOPS, phosphate, Tris) are strongly preferred for pH control.
Practical guidance for assay buffers (general):
Prepare nojirimycin in the assay buffer of choice (e.g., 50 mM sodium phosphate, pH 6.5–7.5; or 50 mM MES, pH 5.5–6.5 for many glycosidases) rather than relying on the compound to influence pH.
If the salt form is unknown, titrate final solutions to target pH after addition, as addition of an amine-containing analyte can slightly shift pH in low-buffer-capacity media.
Literature note (general):
The conjugate-acid pKa of iminosugars often lies near neutral pH; however, this does not endow sufficient buffering capacity at practical concentrations. Choose a buffer with pKa within ±1 unit of your target pH and adequate ionic strength for the enzyme system.
Summary: Use standard buffers for pH control; dissolve nojirimycin into those systems at the required concentration and verify pH post-addition.
Green Alternatives
Although nojirimycin is a reagent/ligand rather than a solvent, greener choices arise in how you process, derivatize, and purify this highly polar iminosugar.
Greener media for dissolution and reactions (general guidance):
Prefer water or water–ethanol mixtures for simple transformations (e.g., salt formation, reductive amination with water-tolerant catalysts). Many iminosugar modifications proceed efficiently in aqueous ethanol.
Use bio-based solvents where feasible (ethanol, isopropanol) instead of DMF/NMP for protection or acylation steps. Switch to carbonate bases and catalytic DMAP in alcohols for O-acylation when selectivity permits.
For protections requiring acetals, acetone (often acceptable on solvent guides) under catalytic acid is typically greener than chlorinated options.
Workup and purification:
Replace large-volume normal-phase silica runs with aqueous ion-exchange or HILIC chromatography; these reduce halogenated solvent consumption.
Employ crystallization of acid salts (e.g., HCl salt) from ethanol/water to avoid chromatographic waste.
Small comparison (general):
Conventional: DMF, DCM, and large silica columns for benzylations/acylations.
Greener alternative: ethanol/water or 2-propanol/water for reactions; aqueous ion-exchange or HILIC for purification; supercritical CO2 is generally not suitable due to extreme polarity.
Trade-offs:
Water-rich media may slow rates for some protections and can complicate moisture-sensitive steps; in such cases, minimal-use polar aprotics (acetonitrile, Me-THF blends) with recovery programs can mitigate impact.
HILIC/IEC require method development but pay dividends in solvent reduction.
Pharmaceutical Uses
Scope: Information below is provided strictly in a research/formulation context. This product is for laboratory research use only; no therapeutic claims are made.
Literature/general (not item-specific):
Reference material: Nojirimycin is frequently used as a reference standard for analytical methods assessing iminosugar content, impurity profiling, or glycosidase-inhibitor panels.
Excipient status: It is not a common pharmaceutical excipient. Its strong hydrophilicity and amine functionality can, however, aid in salt formation studies and in designing model systems for permeability and transporter investigations.
Formulation studies: Owing to its high aqueous solubility, it serves as a model polar analyte for developing HILIC and ion-exchange methods, lyophilization cycles, and stability-indicating assays under various pH/ionic-strength conditions.
Structure–property analoging: Researchers often compare nojirimycin with N-alkyl analogs to study how basicity and hydrophilicity impact dissolution, hygroscopicity, and solid-state behavior (hydrate formation, TGA/DSC profiles).
Practical considerations for R&D:
Specify salt form (free base vs hydrochloride/TFA) in all documentation; counterion significantly impacts hygroscopicity and assay response.
For stability studies, monitor for Maillard-type discoloration in the presence of reducing sugars/amines under heat; store under controlled humidity.
Analytical controls: Include orthogonal methods (HILIC-ELSD or PAD, plus MS) because UV response of unmodified iminosugars is weak.
Physical Properties
From Product Data (item-specific):
Appearance: 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 (general reference; not item-specific):
Physical state: typically a crystalline, highly hydrophilic solid (iminosugar)
Melting behavior: often reported as a high-melting solid that may darken/decompose on heating; exact MP varies by form and hydration (consult primary literature/CoA for your lot).
Solubility profile: very soluble in water; soluble to moderately soluble in polar protic solvents (methanol, ethanol); sparingly soluble in DMSO; practically insoluble in aprotic/nonpolar media (Et2O, hexanes, toluene).
Ionization: endocyclic secondary amine readily protonated in water; conjugate acid pKa commonly reported near physiological pH (literature ~7–8 depending on counterion and ionic strength).
Hygroscopicity: polyol amines can be hygroscopic and may form hydrates or pick up moisture.
Partitioning: strongly hydrophilic; expected negative logP and very low logD at neutral pH.
Practical implications for use:
Expect rapid dissolution in water and buffered aqueous media; warming to 30–40 C and gentle stirring can accelerate dissolution at high concentrations.
For NMR, D2O is generally preferred; addition of a trace acid (e.g., DCl) can sharpen signals by suppressing exchange.
Precise numerical specifications (density, MP, pKa, logP, refractive index) should be verified on the CoA/Spec Sheet for the supplied lot.
Quality and Grades
From Product Data (item-specific):
Grade: Moligand™
What Moligand™ typically signifies (general, brand-level guidance):
The Moligand™ line is curated for small-molecule libraries and ligand-discovery workflows. Materials are selected for identity traceability (CAS/CID alignment), screening-suitable purity, and compatibility with common assay media.
Emphasis is placed on consistent lot-to-lot performance for biochemical screening (e.g., enzyme panels), medicinal chemistry hit validation, and chemoinformatics-ready metadata.
Practical implications for this item:
Identity and registry alignment: Provided CAS (15218-38-9) and PubChem CID (65242) support ELN registration and procurement traceability.
Purity: A specific assay or purity threshold is not listed here. Not specified for this item; refer to CoA/Spec Sheet.
Counterions/solvent of crystallization: Iminosugars may appear as free base or as acid salts/hydrates depending on preparation. The exact form for this SKU is not stated here. Verify on CoA (important for mass balance and solution molarity).
Residual solvents/metals/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Recommended quality checks on receipt (good practice):
Proton NMR in D2O to confirm diagnostic piperidine protons and polyol pattern; integration checks hydration/solvent content.
HRMS or LC–MS for molecular ion confirmation.
Karl Fischer moisture only if hydration level impacts your assays.
Documentation: Request and retain the lot-specific CoA and SDS to complement this catalog entry for regulated or GLP-like environments.
Reaction and Applications
From Product Data (item-specific):
Manufacturer applications: Not specified for this item in the catalog entry.
Enzymology tool: Classic transition-state mimic of glycoside hydrolysis used as a reference inhibitor probe for retaining glycosidases in biochemical assays and mechanistic studies.
Scaffold for SAR: Parent iminosugar core enables systematic N-alkylation/acylation to tune potency and selectivity across glycosidase families (e.g., glucosidase, mannosidase).
Synthetic intermediate: A versatile chiral polyol–amine for preparing glycomimetics, spiro-oxazolidinones, and multivalent iminosugar conjugates.
Typical transformations and tips (general):
Nitrogen protection: Boc or Cbz to control basicity and direct downstream O-protection; Boc introduction commonly via Boc2O/NEt3 in aqueous/MeOH biphasic or DMF.
O-protection: Selective acetonide formation (2,3- or 3,4-) in acetone/acid; benzylation under phase-transfer for permanent protection removable by hydrogenolysis.
N-alkylation: Reductive amination with aldehydes/ketones (NaBH3CN or catalytic hydrogenation) affords N-substituted analogs; careful pH control avoids over-alkylation.
Glycosylation analogs: Mitsunobu coupling of primary alcohol can generate inverted iminosugar ethers; enzyme-catalyzed derivatizations exploit proximity effects.
Salt formation/purification: Convert to hydrochloride or other salts to improve crystallinity and facilitate isolation from aqueous media.
Practical advice:
Use ion-exchange chromatography (Dowex 50WX) or HILIC/amine columns for purification of highly polar derivatives.
Monitor by HILIC-MS or derivatize with dansyl/benzoyl groups to enhance UV response in analytical HPLC.
For multi-step protection sequences, map out hydrogen-bonding patterns; regioselectivity often follows well-defined conformational preferences of the piperidine chair.
Reaction Conditions
The following guidance summarizes commonly reported conditions for transforming iminosugars like nojirimycin. Adjust based on your substrate, protection pattern, and scale.
Nitrogen protection (general literature):
Boc protection: Boc2O (1.2–1.5 equiv), base (NEt3 or NaHCO3), solvent MeOH or mixed MeOH/H2O, 0–25 C, 2–16 h; monitor by HILIC.
Cbz protection: CbzCl (1.1–1.3 equiv), Na2CO3 (aq), biphasic THF/H2O, 0–25 C; extract as salt or isolate by ion exchange.
O-protection/benzylation:
Benzylation: BnBr (2–4 equiv), NaH or K2CO3, DMF or acetonitrile, 0–25 C, 2–12 h; protect N first to avoid N-benzylation. Hydrogenolysis (Pd/C, H2 1–3 atm, MeOH/H2O) removes Bn.
Acetonide formation: acetone with catalytic acid (p-TsOH or CSA), 0–25 C; remove water (molecular sieves) to drive selectivity (commonly 2,3- or 3,4-acetonide).
Reductive amination (N-alkylation):
Carbonyl partner (1.2–3 equiv), NaBH3CN (1.5–2 equiv) or BH3·THF, solvent MeOH or MeOH/AcOH (pH 5–6), 0–25 C, 2–24 h; avoid strong acid to prevent imine hydrolysis.
Oxidation at C-6 (primary alcohol):
TEMPO/NaOCl (pH 9–10, 0–5 C) or Dess–Martin (DCM/MeCN) affords aldehyde/acid; ensure N is protected to minimize side reactions.
Purification:
Cation-exchange (Dowex 50WX) eluting with NH4OH or volatile buffers; for neutral protected intermediates, silica gel with EtOAc/MeOH gradients.
Yields and times:
Highly substrate- and protection-dependent; literature reports commonly range 50–85% for single-step protections and 40–70% for multi-step elaborations. Optimize on small scale first.
Note: These are general literature conditions for iminosugars and are not specifications for this catalog item.
Safety and Handling
From Product Data (item-specific):
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
Hazard (H) statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
General safety profile (literature/general; not item-specific):
Nojirimycin is a polyhydroxylated amine. Such compounds typically present low flammability and low volatility. Principal risks are eye/skin irritation and, if dust is generated, respiratory tract irritation.
Not known as a strong sensitizer; however, amines may cause allergic responses in susceptible individuals.
Best solvents: water and aqueous buffers; good in methanol/ethanol; variable in DMSO; poor in aprotic/nonpolar solvents.
Salt formation (e.g., HCl, TFA salts) often further increases water solubility and can improve dissolution kinetics.
Practical guidance for stock solutions:
Enzymology/screens: prepare in water or buffer (e.g., 10–100 mM stocks) and, if needed, sterile-filter through 0.22 µm.
Medicinal chemistry assays: DMSO stocks are sometimes used for library compatibility, but maximum solubility may be limited; consider concentrated aqueous stocks with back-addition to assay wells.
NMR: D2O is preferred; for slower exchange or to resolve coupling, mild acidification (e.g., 1–2% DCl) can help.
Co-solvent strategies (general tips):
Warm (30–40 C) water or buffered saline often dissolves quickly; brief sonication helps for stubborn pellets.
Avoid attempting dissolution in nonpolar media; if anhydrous conditions are needed for derivatization, convert to protected derivatives first (e.g., acetonide/benzyl ethers, Boc on N).
When to choose nojirimycin vs alternatives:
Select nojirimycin when a neutral (free-base) iminosugar scaffold is required for glycosidase engagement or for synthetic elaboration; choose 1-deoxynojirimycin or N-alkyl analogs when altered basicity or lipophilicity is desired for SAR.
Storage and Reconstitution
From Product Data (item-specific):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (good practice; not item-specific):
Solid storage: Keep tightly closed in the original container at ambient temperature, protected from excessive humidity. Given the polyol/amine nature, mild hygroscopicity is possible; include desiccant if storing long term.
Light and air: No special light sensitivity is typically reported; store in a dry place. Avoid prolonged exposure to high heat.
Reconstitution: For biochemical use, dissolve directly in deionized water or appropriate buffer to prepare 10–100 mM stocks. Gentle warming (30–40 C) and vortexing/brief sonication facilitate dissolution.
Sterility: For cell-free enzyme assays, 0.22 µm filtration of aqueous stocks is recommended. For cell-based screening, prepare fresh or aliquot and freeze to minimize contamination.
Aqueous stock stability: Iminosugars are generally stable in neutral aqueous solutions for days at 2–8 C; for longer storage, aliquot and freeze at −20 C to −80 C. Avoid repeated freeze–thaw cycles; thaw on ice and mix before use.
Counterion awareness: If supplied as a salt (e.g., hydrochloride), adjust pH of working buffers after addition to maintain assay conditions.
Documentation:
For exact shelf life, salt form, and any stabilizers: Not specified for this item; refer to CoA/Spec Sheet and SDS for the supplied lot.
Structure and Identity
Brief overview: Nojirimycin is a polyhydroxylated iminosugar (a piperidine analog of D-glucopyranose) widely used as a glycosidase probe and glycomimetic building block.
From Product Data (item-specific):
SKU: N612355
Product name: nojirimycin
CAS: 15218-38-9
CID: 65242
InChIKey: 24250 (as provided in catalog record)
Grade: Moligand™
Storage conditions: Room temperature
Research use note: For research use only
Literature identity (general reference, not item-specific):
Compound class: iminosugar (endocyclic nitrogen replacing the ring oxygen of glucopyranose)
Typical ring system: six-membered piperidine ring in a pyranose-like chair conformation
Common synonyms: nojirimycin (NJ); 5-amino-5-deoxy-D-glucopyranose (imino-D-glucose)
Molecular formula (literature): C6H11NO5
Molecular weight (literature): ~177.16 g/mol
2D structural description in words: a chair piperidine ring bearing hydroxyls at positions analogous to D-glucose (C-2, C-3, C-4) and a primary hydroxymethyl substituent at C-6; the ring heteroatom is nitrogen (–NH–) in place of the anomeric oxygen.
Notes:
SMILES and definitive InChIKey for the exact stereochemistry should be taken from a trusted database (e.g., PubChem CID 65242). Use those for registration-sensitive workflows.
Always reconcile any registry identifiers against your internal ELN before scale-up or informatics integration.
Synthetic Utility
Nojirimycin’s densely functionalized, chiral polyol–amine framework makes it a powerful synthon for glycomimetic chemistry.
Functional-group handles (general):
Endocyclic secondary amine: amenable to protection (Boc, Cbz), N-alkylation (reductive amination/alkyl halides), and acylation (amide/urea formation).
Polyol array: selective acetalizations (2,3- or 3,4-acetonide), benzylations, silylations (TBS/TBDPS) enable regio- and chemoselective derivatization.
Primary alcohol (C-6): oxidation to aldehyde/carboxylate for conjugation; activation for ether/ester formation.
Strategic uses (literature/general):
Access to N-alkylated iminosugars: libraries targeting differential glycosidase inhibition profiles; often prepared via reductive amination or Mitsunobu-based N–C tethering.
Conjugates and multivalency: attachment to polymers, peptides, or dendrimers to explore avidity effects in enzyme binding.
Retrosynthetic value: Serves as a chiral pool starting point for bicyclic iminosugars, azasugars, and C-linked analogs of glucose/mannose.
Purification/analysis tips:
Use cation-exchange resins (H+ form) for isolating basic products; elute with ammonia or dilute base.
For analytical HPLC, HILIC with amine-compatible mobile phases (ACN/water with ammonium formate) yields sharp peaks; derivatize with UV tags if needed.
Cautions:
Protect amino group prior to strong base or electrophile exposure to avoid undesired N/O-alkylation scramble.
Water content profoundly affects regioselectivity in acetalizations; dry solvents and controlled acidity are key for reproducibility.
Target Specificity
From Product Data (item-specific):
Target, antigen, epitope, clone, isotype, species reactivity: Not applicable/not specified for this small-molecule product.
Literature context (general; not item-specific):
Nojirimycin is widely used as a probe for retaining glycosidases in biochemical studies; however, specific “targets” (e.g., enzyme isoforms, Ki values) vary with assay conditions, enzyme source, and structural modifications. For precise target data, consult primary literature and determine under your exact assay 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 15218-38-9. InChIKey BGMYHTUCJVZIRP-GASJEMHNSA-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.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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