Kifunensine - Moligand™,≥98% , CAS No.109944-15-2

CAS: 109944-15-2 Cat. No.: K274698 Formula: C₈H₁₂N₂O₆ Molecular Weight: 232.19 EC Number: 634-573-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

FR-900494 | (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Kifunensine is an effective selective inhibitor of type I α-mannosidases that can be isolated from actinomycetes. It can prevent the trimming of mannose residues on glycoproteins by α-mannosidases I. Kifunensine can inhibit the endoplasmic reticulum-related protein degradation pathway.

Specifications

Synonyms

FR-900494 | (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione

Specifications & Purity

Moligand™,≥98%

Biochemical and Physiological Mechanisms

Cell-permeable, potent, selective inhibitor of class I α-mannosidases. (IC 50 = 20-50 nM for\xa0mung bean α-1,2-mannosidase I). Alkaloid originally isolated from the actinomycete Kitasatosporia kifunense . Used to suppress Endoplasmic Reticulum-Associated

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.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

504757004

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504757004

Canonical Smiles

C(C1C(C(C(C2N1C(=O)C(=O)N2)O)O)O)O

IUPAC Name

(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-2,3-dione

InChIKey

OIURYJWYVIAOCW-PQMKYFCFSA-N

INCHI

1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1

Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H]2N1C(=O)C(=O)N2)O)O)O)O

Molecular Weight

232.19

Reaxy-Rn

38226983

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38226983&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Imidazopyridines Piperidines Imidazolidinones Tertiary carboxylic acid amides Secondary carboxylic acid amides Secondary alcohols Lactams Polyols Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - Imidazopyridine - Imidazolidinone - Piperidine - Imidazolidine - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Secondary carboxylic acid amide - Secondary alcohol - Azacycle - Organoheterocyclic compound - Polyol - Organooxygen compound - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: Not available

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GH92 alpha-mannosidase (372 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water to 10 mM (with warming)
• Melt Point(°C): >208°C (dec.)
• Molecular Weight: 232.190 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 232.07 Da
• Monoisotopic Mass: 232.07 Da
• Topological Polar Surface Area: 130.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 334.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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

Application Protocols

No tested or validated protocols are provided in the Product Data for this SKU.

• Recommended working concentrations, dilution schemes, assay panels, or positive controls: Not specified for this item; users should develop and validate protocols suitable for their specific system.
• For general solution handling, see Solvent Selection and Reaction Conditions. Always consult the SDS and your institutional SOPs.

Biological Roles

Context for researchers (literature/general):

• Kifunensine is a well-established small-molecule tool in glycobiology research, commonly employed to perturb N-linked glycan processing pathways in the secretory pathway. By modulating early mannose trimming steps, investigators can study quality control mechanisms, ER-associated pathways, and glycoprotein folding/trafficking.
• Use cases include producing research-grade proteins enriched in high-mannose glycans for analytical method development (e.g., glycoproteomics, endoglycosidase mapping) and for evaluating glycan-dependent interactions in vitro.
• In cell culture, transient exposure enables controlled changes to glycan profiles without genetic manipulation, facilitating comparative studies between treated and untreated populations.

Important caveats:

• Effects may be cell-type and context dependent; empirical titration and time-course studies are recommended.
• Avoid clinical or in vivo extrapolation—this product is for research use only.

Item-specific biological activity parameters (potency, Ki/IC50, selectivity): Not specified for this item; consult primary literature and perform in-system validation.

Buffer Applications

This product is not a buffering reagent. However, it is commonly dosed into buffered biological media in research settings.

Practical notes (general):

• Compatible with standard biological buffers (e.g., PBS, HEPES-buffered media) when delivered from a concentrated stock solution.
• Ensure complete dissolution before dosing; filter sterilize solutions prepared for cell culture if required by aseptic practice.

Item-specific buffer recipes, pH ranges, or concentrations: Not specified for this item; refer to CoA/Spec Sheet and validate in your system.

Green Alternatives

As a solid bioactive compound used at low concentrations, the “greenness” considerations focus on solvent choice and handling rather than replacing the molecule itself.

Greener handling considerations (general):

• Prefer water or buffered aqueous media when feasible to avoid organic solvent use.
• If organic cosolvent is required, minimize DMSO or alcohol content to the lowest effective percentage.
• Prepare higher-concentration stocks to reduce solvent volumes and shipment of dilute solutions.

Comparison of solvent options (general):

• Water/buffer: highest EHS profile; compatible with most biochemical assays; confirm stability and solubility.
• DMSO: effective solubilizer; use sparingly due to environmental and biological considerations; manage waste appropriately.
• Alcohols (EtOH/MeOH): moderate environmental impact; consider flammability and biological effects.

Packaging and storage:

• Product is shipped cold and stored at −20°C, minimizing degradation and waste. Maintain desiccation to reduce hygroscopic uptake and preserve shelf life.

Note: There are no “alternative actives” to kifunensine within this listing; selection of different tool compounds should be based on scientific rationale rather than green chemistry alone.

Pharmaceutical Uses

No excipient or pharmacopeial role is provided for this item.

• Scope: This listing is supplied for laboratory research only (discovery, screening, analytical studies). It is not formulated, certified, or intended for human or veterinary use.
• Process development research (general): In bioprocess and analytical development research, tool compounds like kifunensine may be introduced in cell culture studies to explore how altered glycosylation affects downstream processing and analytics. Such use remains firmly within research contexts.

Regulatory/compendial status:

• Pharmacopeial monographs, GMP status, or clinical-grade specifications: Not specified for this item; not intended for clinical applications.

Any claims of therapeutic benefit are outside the scope of this product and are not made.

Physical Properties

Item-specific specifications are not provided in the Product Data. Refer to the CoA/Spec Sheet for definitive values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Typical values are reported in the literature for kifunensine, but item-specific specs are not provided.)
• Boiling point: Not applicable/Not reported (decomposes before boiling; literature trend for polyhydroxylated alkaloids).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for a solid; not specified.
• pKa/logP: Not specified for this item; refer to CoA/Spec Sheet. (Literature describes kifunensine as a highly polar, polyhydroxylated amine with overall hydrophilic character.)
• Solubility: Not specified for this item; refer to CoA/Spec Sheet. (Literature/general: typically soluble in polar media such as water, aqueous buffers, and DMSO.)

General physicochemical profile (literature/general):

• Polar, hydrogen-bond rich small molecule; strong tendency for aqueous solubility compared to apolar organic solvents.
• Hygroscopicity can be observed for polyols; handle under dry conditions as recommended under Storage.

Quality & Grades

• Grade/Purity: Moligand™ (per Product Data).

What Moligand™ implies (general description):

• Moligand™ designates compounds curated for small-molecule/ligand discovery and screening applications. Typical expectations include high chemical purity suitable for biochemical assays, accurate identity confirmation (e.g., LC–MS/HRMS, NMR), and lot-to-lot consistency aimed at screening workflows. Exact specifications for this SKU (e.g., residual solvent limits, assay %) are not provided here—refer to the CoA/Spec Sheet.

Stabilizers and additives:

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

Analytical documentation and suitability:

• Identity/purity confirmation: Expect LC–MS and/or NMR data provided on the CoA for the specific lot. UV cutoff, water/peroxide/metal limits are Not specified for this item; refer to CoA/Spec Sheet.
• Use case: Appropriate for in vitro research, target engagement studies, and cell-based assay development where consistent potency and minimal assay interference are required.

Practical notes:

• Upon receipt, verify lot documentation (CoA) for assay purity and identity.
• For sensitive biological assays, consider preparing fresh stock solutions and performing a small pilot dose–response to confirm activity with your system.

Reaction & Applications

This product is primarily a bioactive research compound rather than a synthetic reagent. Accordingly, its laboratory applications are predominantly in chemical biology and glycobiology rather than as a stoichiometric reactant.

Research applications (literature/general):

• Widely used as a biochemical tool in glycoprotein processing studies to modulate N-glycan maturation, enabling enrichment of high-mannose glycoforms for analytical characterization and mechanism studies.
• Employed in cell culture workflows to standardize glycosylation patterns of secreted proteins, facilitating downstream purification and structure–function analyses.
• Utilized in target validation assays probing endoplasmic-reticulum-associated glycan trimming enzymes.

Assay design notes (general practice):

• Prepare concentrated DMSO or aqueous stock; validate solubility and absence of precipitation upon dilution into assay media.
• Include solvent controls to account for any DMSO effects.
• Titrate compound to determine concentration–response relationships in the specific cell line or enzyme system.

Synthetic chemistry usage:

• Not typically used as a reagent or catalyst in synthetic transformations. For synthetic considerations, see “Synthetic Utility” (largely non-applicable for this item).

Item-specific application claims from manufacturer: none provided beyond Research Use Only.

Reaction Conditions

This compound is not typically used to drive chemical reactions; instead it is dosed as a solution into biological systems. Consequently, there are no standard “reaction conditions” in the synthetic sense for this SKU.

General solution preparation (research practice):

• Solvents: water/buffer or DMSO are commonly used carriers in biochemical/cell-based assays.
• Concentrations: prepare concentrated stock solutions suitable for your assay, then dilute into media while keeping any organic cosolvent low. Exact concentrations are assay-dependent and must be empirically determined.
• Temperature and light: prepare and store solutions at low temperature when possible; avoid prolonged exposure to elevated temperature and light to limit degradation.

Expected yields, catalysts, or time courses (synthetic context): Not applicable.

Item-specific preparation instructions: Not specified for this item; refer to CoA/Spec Sheet and SDS.

Safety & Handling

Authoritative safety data must be taken from the product-specific SDS.

• 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 precautions (good practice):

• PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves.
• Engineering controls: handle powders in a fume hood or containment to minimize dust/aerosol; avoid inhalation and contact.
• Handling: avoid moisture uptake; kifunensine is a polyhydroxylated amine and may be hygroscopic—keep containers tightly closed and desiccated.
• Incompatibilities: strong oxidizers and strong acids/bases may cause degradation; avoid prolonged exposure to elevated temperature and light.
• First aid (overview; consult SDS): if inhaled—fresh air; if on skin—wash with soap and water; if in eyes—rinse cautiously with water for several minutes; if ingested—rinse mouth, seek advice.
• Waste: dispose according to institutional and local regulations for organic laboratory chemicals.

Shipping/storage risk controls:

• Shipped: Ice chest + ice pads (per Product Data) to limit thermal stress.
• Storage: Store at −20°C, desiccated (per Product Data). Minimize freeze–thaw by aliquoting after first opening.

Solvent Selection

Kifunensine is a polar, polyhydroxylated small molecule. Solvent choice is driven by assay compatibility and solubility.

General solvent behavior (literature/general):

• Aqueous media: typically soluble in water and common biological buffers (e.g., PBS, HBSS) due to multiple hydroxyls and a tertiary/secondary amine.
• Polar aprotic: readily soluble in DMSO; DMSO stocks are commonly used for screening assays.
• Alcohols: methanol/ethanol may dissolve kifunensine but are less common for biological dosing.
• Nonpolar organic solvents (e.g., hexanes, toluene): poor solubility expected.

Selection guidance:

• For cell-based or enzymatic assays: prepare concentrated DMSO stocks and dilute into aqueous buffer, keeping final DMSO below cell-tolerated limits (often ≤0.1–0.5%, lab practice).
• For purely biochemical in vitro work where DMSO is undesirable, direct dissolution in water or buffer may be feasible; adjust pH only if necessary and validated.

Quick comparison (general):

• Water/buffer: highest biological compatibility; verify complete dissolution.
• DMSO: excellent solubilizer; monitor final DMSO percentage.
• Methanol/ethanol: secondary choice; consider effects on proteins/cells.

Item-specific solubility values: Not specified for this item; refer to CoA/Spec Sheet.

Storage & Reconstitution

Item-specific conditions (from Product Data):

• Storage: Store at −20°C, desiccated.
• Shipment: Ice chest + ice pads.

Reconstitution:

• Item-specific reconstitution solvent, concentration, and filter-sterilization guidance: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance (good practice):

• Allow vial to equilibrate to room temperature in a desiccated environment before opening to prevent condensation.
• Prepare single-use aliquots of any stock solutions to avoid repeated freeze–thaw cycles.
• Use clean, dry tools to avoid introducing moisture.

Stability:

• Long-term stability data, solution stability, and retest/expiry: Not specified for this item; consult the CoA and perform in-lab verification as needed.

Structure & Identity

Brief description: Kifunensine is a polyhydroxylated, bicyclic indolizidine alkaloid widely used as a research tool compound in glycobiology.

• SKU: K274698
• Product Name: Kifunensine
• CAS: 109944-15-2
• CID: 130611
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a truncated key.)
• 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.

Structural features (literature/general):

• Core scaffold: indolizidine (fused bicyclic azabicyclo framework with a bridgehead nitrogen).
• Functional groups: multiple secondary alcohols (polyhydroxylated), typically no aromatic rings; overall highly polar neutral amine or hemiaminal character depending on tautomeric form (literature).
• Stereochemistry: multiple defined stereocenters across the bicyclic ring system; kifunensine is a single, well-defined stereochemical entity (literature).
• 2D description in words: a fused five–six membered ring containing one ring nitrogen (indolizidine), bearing several vicinal hydroxyl substituents around the saturated backbone; no extended conjugation.

Identity notes:

• Category Path: 全部 / 可售 / 小分子和化合物库 (small-molecule library entry, research-only).
• Research Use Note: For research use only.

Synthetic Utility

Kifunensine is generally the end product (a bioactive tool compound) rather than a synthetic intermediate or reagent.

• Functional group reactivity (general): Multiple alcohols and a tertiary/secondary amine within a saturated bicyclic system could, in principle, undergo protection/deprotection, acylation, carbamate formation, or salt formation. However, such transformations are typically part of kifunensine’s total synthesis or derivatization studies rather than routine laboratory use.
• Named reactions: Not commonly employed as a reagent/catalyst in named organic reactions.

Use in synthesis workflows:

• If derivatization is desired for probe development (e.g., attaching reporter tags), strategies often target alcohol functionalization (e.g., carbonate/carbamate linkers) or amine modification with careful retention of stereochemistry (literature/general guidance).

Item-specific synthetic specifications (reactivity, protective group strategies, etc.): Not specified for this item; consult primary literature for total synthesis/derivatization methods.

Target Specificity

Target/biological specificity details are not provided in the Product Data for this SKU.

• Target name, selectivity profile, potency metrics: Not specified for this item; refer to CoA/Spec Sheet or primary literature.
• Antigen/epitope/clone/isotype (antibody-style metadata): Not applicable for a small-molecule research compound.

Note: Any mechanistic or target discussions elsewhere are general literature context and are not item-specific claims.