This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
External Descriptors
Not available
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
321.370 g/mol
XLogP3
-4.300
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Exact Mass
321.19 Da
Monoisotopic Mass
321.19 Da
Topological Polar Surface Area
163.000 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
389.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
9
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
Lösungsrechner
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
No tested bioassay/diagnostic protocols are provided for this small-molecule product. Application protocols depend on the intended research context:
For chemical synthesis: Follow standard aminocyclitol derivatization procedures (see Reaction Conditions and Synthetic Utility tabs). Validate stoichiometry and protection strategies at small scale.
For biochemical assays: Prepare aqueous stock solutions (e.g., 10–100 mM) in buffer adjusted to pH 6–7 with compatible counterions (e.g., HCl, acetate). Filter-sterilize through 0.22 μm if required. Confirm concentration by quantitative NMR or UV (if a chromophore is introduced; native garamine lacks strong UV above 220 nm).
For chromatographic analysis: Use RP-HPLC with acidic modifiers (0.1% formic or acetic acid) or HILIC; consider ion-exchange for purification.
Item-specific validated applications, recommended dilutions, and positive controls: Not specified for this item; refer to CoA/Spec Sheet or contact Aladdin Scientific for technical support.
Biological Roles
Literature/general context (biochemistry; no clinical claims):
Structural motif: Garamine-like aminocyclitols comprise polycationic, hydrogen-bond-rich frameworks found as substructures in many aminoglycosides. Their dense array of hydroxyls and amines enables strong binding to polyanionic biomolecules.
Nucleic acid interactions: Polycationic aminocyclitols can engage A-site RNA motifs via electrostatic and hydrogen-bond interactions. Garamine-derived fragments are used as probes to study the role of individual ring systems and substituents in ribosomal binding.
Enzyme recognition: Aminoglycoside-modifying enzymes (acetyltransferases, nucleotidyltransferases, phosphotransferases) exhibit selective activity toward specific amine/diol patterns on aminocyclitol cores. Garamine analogs are applied to dissect enzyme specificity and resistance mechanisms.
Transport and permeability studies: Due to high polarity and positive charge at physiological pH, garamine scaffolds are models for studying uptake through porins, polyamine transport, and membrane interactions in bacterial systems (in vitro biochemical models).
Conjugate chemistry: Garamine derivatives bearing reporter tags (fluorophores, biotin) facilitate pulldown assays and imaging of RNA-binding events and protein–ligand interactions in cell-free systems.
Important:
The above reflects general biochemical roles of aminocyclitol fragments in research settings. Item-specific biological data, targets, or potencies are not provided for this product; consult primary literature for your assay system.
Buffer Applications
Garamine itself is not a conventional buffering agent. As a polyamine, it can accept protons and form salts, but defined buffering capacity and pKa assignments vary by substitution and are not standardized like dedicated buffers (e.g., Tris, HEPES).
Suitability: Not typically used as a primary buffer. It may contribute to ionic strength and pH stabilization within a narrow range when present as a conjugate acid/base, but this is application-specific.
Practical note (literature/general): If preparing aqueous stock solutions of garamine for biochemical assays, dissolve in an appropriate buffer (e.g., 10–50 mM HEPES or phosphate) and adjust pH after addition, as protonated garamine can shift pH.
For robust, well-characterized buffering systems, use established buffers and add garamine as a solute or ligand under controlled pH.
Item-specific buffer-related specifications: Not applicable / Not specified for this item; refer to CoA/Spec Sheet if pH or counterion information is required.
Green Alternatives
Greener choices relate mainly to solvent systems and protecting-group chemistry rather than the core scaffold.
Replace DMF with safer dipolar aprotics where feasible:
Alternatives: Cyrene, NBP (N-butylpyrrolidone), or propylene carbonate for amidations and couplings.
Favor protic green solvents for workups and transformations:
Water, ethanol, isopropanol often dissolve aminocyclitol salts well and reduce solvent hazard.
Use water-promoted reactions:
Aqueous-phase reductive aminations (NaBH3CN alternatives: picoline borane) and enzymatic glycosylations can minimize organic solvent use.
Small comparison (general):
DMF vs Cyrene: Cyrene offers lower toxicity/biodegradability advantages; viscosity is higher and may slow mass transfer; some base-sensitive reactions require optimization.
DCM vs EtOAc/2-MeTHF: For extractions, EtOAc or 2-MeTHF provide improved environmental profiles; note the high hydrophilicity of garamine salts may necessitate ion-pairing or back-extractions.
TFA vs AcOH/HCl (aq): For ion-pairing in LC or for salt formation, acetic acid or dilute HCl in water can replace TFA to reduce fluorinated waste, depending on analytical needs.
Operational practices:
Minimize protecting-group steps via chemoselective catalysis (e.g., boronic-acid-mediated regioselective functionalization of diols) to reduce solvent and reagent loads.
Implement reverse-phase chromatography with aqueous eluents to limit halogenated solvent use.
Note: These are general green-chemistry considerations for aminocyclitol work; adapt to your process requirements.
Pharmaceutical Uses
No therapeutic or clinical claims are made. The following relates to formulation and process chemistry in research/manufacturing contexts (literature/general):
Synthetic intermediate: Garamine-type aminocyclitols serve as intermediates in the assembly of aminoglycoside analogs during medicinal chemistry campaigns and process route scouting for APIs in the aminocyclitol class.
Salt forms: Protonated mineral-acid salts (e.g., hydrochloride) are frequently used to improve crystallinity, handling, and aqueous solubility during isolation and purification. Note: The specific salt form of this catalog item is Not specified; refer to CoA/Spec Sheet.
Analytical development: Due to high polarity, reverse-phase LC with ion-pairing modifiers or HILIC is often employed for in-process control assays; MS-friendly acids (formic/acetic) are preferred for LC–MS.
Excipient role: Not typical. Garamine is not used as a standard excipient; its role is generally as a synthetic building block or research tool compound.
Regulatory context:
Pharmacopeial monographs: None commonly associated with garamine as a standalone substance (literature check advisable if needed).
Always verify impurity limits, residual solvents, and counterion content per your internal quality system when using garamine-derived materials in GMP-adjacent development work.
Physical Properties
Item-specific physico-chemical specifications have not been provided for this catalog entry.
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.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not applicable/rarely reported for polyhydroxylated polyamines (decompose before boiling) (literature, general).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable (solid) or not commonly reported for this class.
pKa: Aminocyclitols typically exhibit multiple basic pKa values in the range ~7–10 for primary/secondary amines (literature/general guidance; actual values depend on substitution and salt form).
LogP/LogD: Strongly hydrophilic; logP << 0 is typical for polyol polyamines (literature/general); actual value depends on counterion and hydration state.
Solubility (literature/general):
Highly soluble in water and aqueous mineral acids when in protonated/salt form.
Soluble to moderately soluble in polar protic solvents (methanol, ethanol); limited solubility in aprotic polar solvents (DMF/DMSO) can be improved by forming salts.
Practically insoluble in nonpolar solvents (ethers, hydrocarbons).
Important:
Do not treat the above as item specifications. For method validation, QC thresholds, and release testing, use the product’s CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grade (general):
Research/biochemical grade materials are typically suitable for synthetic chemistry, screening libraries, and assay development. If HPLC or LC–MS applications are planned, verify UV-absorbing impurities, inorganic residuals, and water content against your analytical method needs.
For amine-rich polyols such as garamine, relevant quality attributes may include:
Counterion/salt form verification (e.g., free base vs. hydrochloride) by ion chromatography or titration.
Residual inorganic salts and water content (KF) due to hygroscopicity (if applicable).
Identity confirmation by NMR (1H/13C; exchangeable protons often broaden), HRMS, and optical rotation where applicable.
Heavy metal limits and residual solvents per process route, if critical to application.
Best practices:
Request CoA and, if needed, a Spec Sheet outlining assay method, identified salt form, and impurity profile. For structure–activity work, verify amine count/protonation state under your assay conditions.
If using in stereospecific syntheses, confirm stereochemical integrity by chiroptical techniques or comparison to authenticated spectra.
Reaction and Applications
Research and synthesis contexts for garamine (literature/general, aminocyclitol chemistry):
Building block for aminoglycoside analogs: Garamine-type scaffolds are commonly used to assemble or modify the 2-deoxystreptamine/aminocyclitol cores in structure–activity studies toward rRNA A-site binders and to probe resistance enzyme selectivity (without implying therapeutic use).
Glycosylation chemistry: The multiple hydroxyls serve as nucleophiles after selective protection; N-glycosylation onto amine sites or O-glycosylation of protected alcohols enables construction of pseudo-disaccharide aminoglycosides. Activating groups include trichloroacetimidates, thioglycosides, and glycosyl halides.
Protection strategies: Orthogonal protection of amines (Boc, Cbz, Fmoc, Alloc) and diol masking (acetonides, benzylidene, silyl ethers) allow site-selective manipulation. Temporary protection of vicinal diols with cyclic carbonates or boronate esters can direct regioselectivity.
Functional diversification: Reductive amination, acylation (forming amide/urea/thiourea libraries), and carbamate formation expand the chemical space for screening.
Conjugation: Installation of linkers (azido, alkyne) enables click chemistry (CuAAC, SPAAC) to append fluorophores or affinity tags for biochemical probes.
Ion-exchange interactions: As a polycation at physiological pH, garamine derivatives are amenable to immobilization on cation-exchange resins or used as chiral selectors in exploratory separations.
Practical tips:
Use buffered conditions to control protonation state during coupling (pH 7–8 for NHS-esters; 8–9 for epoxide openings).
Carefully dry reagents for water-sensitive steps, but avoid strong bases that can promote elimination or epimerization at protected centers.
Monitor by LC–MS with acidic mobile phases to sharpen peaks of polycations.
Reaction Conditions
General conditions commonly reported for aminocyclitol/garamine derivatization (literature guidance; adjust to your substrate and verify experimentally):
Amide coupling on amines:
Reagents: HATU or EDC·HCl with HOAt/HOBt alternatives; DIPEA or collidine as base.
Solvents: DMF, NMP, or water/MeCN mixtures; temperature 0–25 °C.
Notes: Maintain pH 7–8 in aqueous systems to minimize over-acylation and preserve stereocenters.
Carbamate (Boc) protection:
Reagents: Boc2O (1.1–2.0 equiv), aqueous NaHCO3 or triethylamine.
Solvent: dioxane/water or MeOH; 0–25 °C, 1–4 h.
Cbz protection:
Reagents: CbzCl, Na2CO3 (aq) or K2CO3; biphasic toluene/aqueous buffer or MeOH/water; 0–25 °C.
Reductive amination:
Carbonyl partner (aldehyde/ketone), picoline borane or NaBH3CN; MeOH or MeOH/water with acetic acid (pH 5–6); 0–25 °C, 1–16 h.
O-Protection of diols:
Acetonide: 2,2-dimethoxypropane, catalytic p-TsOH, acetone/Me2C(OMe)2 at 0–25 °C; quench with base.
Benzylidene: benzaldehyde dimethyl acetal, catalytic TsOH; remove by hydrogenolysis later.
Glycosylation onto alcohols or amines:
Donors: trichloroacetimidates/thioglycosides; promoters TMSOTf or NIS/TfOH; solvents DCM/Et2O/MeCN at −40 to 0 °C.
Tips: Rigorous drying; use molecular sieves; monitor for over-glycosylation on multiple nucleophilic sites.
Hydrogenolysis (debenzylation):
Pd/C (5–10%), H2 (1–3 atm), MeOH/water or EtOH/AcOH; 20–25 °C; monitor to avoid over-reduction.
These conditions are representative and not specifications for this item. Optimize per substrate and scale.
Safety and Handling
Safety information specific to this item (GHS classification, pictograms, hazard statements) has not been provided in the product data. Always consult the SDS for authoritative guidance.
General laboratory guidance for polyamines/polyols (literature/practice):
Likely hazards: May cause skin/eye irritation; dust may be irritating to the respiratory tract. Amines can be sensitizers in rare cases. Avoid inhalation of powders and contact with eyes/skin.
PPE: Wear lab coat, nitrile gloves, and safety goggles. Use a dust mask or work in a fume hood when weighing fine powders.
Handling: Hygroscopicity can be an issue for amine salts and polyols; minimize exposure to ambient humidity. Cap promptly after use.
Incompatibilities: Strong oxidizers; isocyanates and acid chlorides (uncontrolled exotherms/derivatization). For free-base amines, avoid CO2 uptake if attempting to maintain defined base content; for acid salts, avoid strong bases that may liberate free amine and ammonia-like odors.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash thoroughly with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Ingestion: Rinse mouth; seek medical advice.
Fire: Organic solids may burn; use water spray, CO2, dry chemical, or foam. Combustion may produce nitrogen oxides.
Notes:
GHS classification, Signal Word, H-statements, and Pictograms: Not specified for this item; refer to SDS.
Solvent Selection
Garamine is an aminocyclitol with high polarity in the literature; dissolution behavior depends strongly on protonation/salt form.
For bioassays/screening: prepare aqueous stock solutions (e.g., 10–100 mM) using dilute HCl or acetate buffer to ensure full dissolution; sterile-filter if required by the assay.
For synthetic transformations: use methanol/ethanol or mixed solvent systems (MeOH–water, THF–water) for protection/deprotection steps; DMSO or DMF can be used for coupling with careful control of base and temperature.
For chromatography: reverse-phase HPLC (water/acetonitrile with 0.1% formic acid or TFA) improves peak shape for polycations; normal-phase silica may cause tailing—use amine-deactivated silica or ion-exchange media.
Comparison (literature/general):
Water vs MeOH: water gives highest solubility for salts; MeOH offers easier removal post-reaction.
DMSO vs DMF: DMSO dissolves highly polar salts slightly better; DMF is easier to remove but may promote side reactions with activated carboxylates.
Note: Item-specific solubility is Not specified for this item; refer to CoA/Spec Sheet.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice for polyamine/polyol solids):
Store tightly capped in a dry environment, protected from prolonged exposure to ambient humidity. Consider using a desiccant in secondary containment.
If the material is supplied as a mineral-acid salt (not specified here), it may be hygroscopic; keep container closed and equilibrate to room temperature before opening to avoid condensation.
Avoid contact with strong oxidizers.
Reconstitution (for assay use):
Dissolve the required amount in water or buffer. If dissolution is slow, add a minimal volume of dilute HCl or acetic acid to assist protonation, then adjust to target pH.
For organic-phase reactions, pre-dissolve in methanol or DMSO before adding to mixed aqueous systems.
Prepare single-use aliquots for sensitive assays; store solutions at 2–8 °C for short term (hours–days) or at −20 °C for longer term, subject to your stability testing. Avoid repeated freeze–thaw cycles.
Item-specific stability, solution shelf life, and salt form: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Structure and Identity
Brief overview: Garamine is referenced in the literature as a polyhydroxylated, polyaminated cyclitol (aminocyclitol) fragment commonly encountered in aminoglycoside chemistry. Item-specific identifiers provided below are limited for this catalog entry.
SKU: G930292
Product name: Garamine
CAS: 49751-51-1 (literature registry number for garamine)
CID: 14699895 (literature, PubChem)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Note: value in the product data is incomplete.)
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 knowledge):
Garamine is typically described as an aminocyclitol scaffold derived from a 1,3,5/1,3,4-trisubstituted cyclohexane core bearing multiple hydroxyl groups and primary/secondary amines.
Functional groups: multiple alcohols (polyol), multiple amines (usually primary) enabling salt formation and extensive hydrogen bonding.
Stereochemistry: several defined stereocenters on the cyclohexane ring typical of sugar/inositol-like frameworks (exact configuration depends on the specific garamine isomer reported in the literature).
2D description in words: a chair cyclohexane ring decorated with vicinal diols and vicinal diamines situated at defined positions; frequently isolated/handled as mineral acid salts (e.g., hydrochloride) in literature to enhance stability and solubility. (Salt form for this catalog item is not specified.)
Notes:
Where specific identifiers (SMILES/InChIKey/formula/MW) are required for method development, consult the item’s CoA/Specification Sheet or contact Aladdin Scientific.
Synthetic Utility
Aminocyclitol chemistry toolbox with garamine scaffolds (literature/general):
Key functional handles:
Multiple primary/secondary amines: amenable to acylation (amides, ureas), carbamate formation (Boc/Cbz/Fmoc protection), reductive amination, and alkylation under controlled conditions.
Polyol motif: selective protection (acetonide, benzylidene, silyl ethers), oxidative cleavage (periodate for vicinal diols when permitted), and activation as sulfonates (mesylates/tosylates) for intramolecular cyclizations.
Named/representative transformations:
Glycosylation: coupling with activated donors (trichloroacetimidates, thioglycosides) to construct aminoglycoside analogs.
Click chemistry: azide/alkyne installation for CuAAC/SPAAC conjugations to fluorophores/biotin.
Reductive amination: installation of sidechains at carbonyl partners in aqueous/alcoholic media using NaBH(OAc)3 or picoline borane.
Urea/thiourea formation: CDI or thiocarbonyldiimidazole with subsequent derivatization.
Retrosynthetic value:
Central cyclitol ring provides a convergence point to append sugar-like appendages and cationic side chains, enabling SAR libraries that modulate charge distribution and H-bonding topology.
Practical considerations:
Employ orthogonal protection to manage differential reactivity of multiple amines (e.g., temporary Boc on primary amines; Alloc on secondary amines).
Perform reactions under mild conditions to preserve stereochemistry; avoid strong bases and high temperatures that can cause elimination or ring-opening in protected intermediates.
Purification often benefits from ion-exchange chromatography or RP-HPLC due to strong silica interactions.
Target Specificity
Not applicable. This product is a small-molecule aminocyclitol, not an antibody or biological with defined antigen/epitope specificity. No target, clone, isotype, or species-reactivity data are associated with this catalog entry.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Dürfen wir Sie über Rabattaktionen informieren?
Später erinnern
Vielen Dank! Bitte überprüfen Sie Ihren E-Mail-Posteingang, um zu bestätigen.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
