Substrate: 0.5–2 mg/mL chitodecaose·HCl in 50 mM sodium acetate, pH 5.2.
Enzyme: serial dilutions in assay buffer.
Incubate 30–60 min at 37 °C; quench by boiling or adding DNS reagent.
Measure absorbance at 540 nm after DNS development; calibrate with glucosamine standards.
Reductive amination labeling at reducing end:
Mix 1–2 mg/mL oligosaccharide with 5–10 mM amino-label in 100 mM acetate buffer pH 5.5.
Add NaBH3CN to 25 mM; react 16 h at RT, protected from light.
Desalt by PD-10 or dialysis; verify labeling by UV/fluorescence and MS if applicable.
Lectin binding by SPR (qualitative):
Immobilize lectin on CM5 chip via amine coupling.
Inject serial dilutions (0.1–2 mg/mL) in HEPES-buffered saline with 0.005% surfactant; maintain pH ensuring solubility.
Regenerate with mild acid if needed; fit sensorgrams with appropriate binding model.
All procedures are for research use only.
Biological Roles
Literature/general context: Chitodecaose (DP≈10 chito-oligosaccharide) is a defined fragment of chitosan/chitin biopolymers derived from β-(1→4)-linked glucosamine. Such fragments are relevant in multiple biological settings, independent of any therapeutic application.
Origin: Generated by partial deacetylation and/or enzymatic hydrolysis of chitin, a structural polysaccharide abundant in fungal cell walls and arthropod exoskeletons.
Metabolic processing: Degraded by chitinases and chitosanases from microbes, plants, and animals, yielding shorter oligomers and monomeric glucosamine that enter hexosamine metabolism.
Molecular recognition: Chain-length dependent binding to lectins and carbohydrate-binding modules; oligomers in the DP 6–10 range often exhibit stronger interactions in several model systems versus shorter oligomers.
Plant systems (research): Recognized by LysM-containing pattern-recognition receptors; deacetylation state and DP influence elicitation potency.
Animal systems (research): Interactions with certain innate immune receptors and serum proteins have been reported; effects are context- and DP-dependent and are used to study basic biology (no clinical claims).
Biophysical properties: Poly-cationic under acidic to neutral pH due to protonated amines; facilitates electrostatic association with polyanions (e.g., DNA, heparin) in model studies.
Note: The above roles are provided for fundamental understanding only and do not imply suitability for clinical or diagnostic use. This product is for research use only.
Buffer Applications
Chitodecaose·HCl is commonly prepared in aqueous buffers for biochemical assays. While it does not serve as a buffering agent itself, solution conditions critically affect solubility and bio-interactions.
Practical preparation (literature/general):
Stock solutions: 1–10 mg/mL in water or buffer. Adjust pH to 4–6 with HCl or acetate to ensure full dissolution; avoid strong base which can decrease solubility and promote side reactions.
Compatible buffers: acetate (pH 4–5.5), MES (pH 5.5–6.5), phosphate (pH ≥6; ensure full dissolution before pH adjustment), citrate (pH 4–6). Maintain moderate ionic strength (10–50 mM) for binding assays sensitive to electrostatics.
Filtration: 0.22–0.45 µm sterile filtration recommended for cell-free assays; for cell-associated research, use aseptic preparation (research use only).
Storage of solutions: prepare fresh or store refrigerated; add 0.02% sodium azide only if compatible with downstream assays and allowed by institutional policies.
Recipe hints:
To make 10 mL of 5 mg/mL solution in 50 mM sodium acetate, pH 5.2: dissolve 50 mg in ~8 mL water, add 1 mL of 0.5 M sodium acetate, adjust pH with acetic acid/NaOH as needed, bring to volume; mix until clear.
For fluorescence labeling workflows, avoid Tris buffers during NHS-ester conjugation (primary amines in Tris compete), and switch to phosphate or bicarbonate as appropriate post-reaction.
Green Alternatives
As a bio-derived, water-soluble oligosaccharide, chitodecaose·HCl is already a comparatively “green” reagent regarding origin and solvent use. Selection of alternatives is driven by experimental needs (DP, acetylation) rather than environmental hazards.
Greener considerations (literature/general):
Solvent system: prefer water or aqueous buffers over organic media; avoid unnecessary organic co-solvents by gently heating and acidifying to pH 4–6 to improve dissolution.
Source material: choose products derived from sustainably processed chitin (e.g., shellfish waste valorization) where supply chain transparency is available.
Biodegradability: chito-oligosaccharides are readily biodegradable; aqueous waste streams are typically low-impact compared to many synthetic polymers (follow local regulations).
Alternatives and trade-offs:
Lower DP chito-oligos (e.g., chitopentaose–chitooctaose): improved diffusion and lower viscosity; may reduce receptor binding in systems requiring longer chains.
Higher DP or chitosan: can enhance multivalency but at the cost of increased viscosity, lower solubility, and more challenging filtration.
Partially acetylated oligomers: closer mimic of native chitin fragments; however, solubility decreases and batch-to-batch control is more complex.
Summary: Optimize DP and acetylation for data quality while keeping water as the primary solvent and minimizing energy input and waste.
Pharmaceutical Uses
No therapeutic claims are made. The following describes formulation-related research contexts reported in the literature for chito‑oligosaccharides; applicability to this specific item depends on its specifications and is for research use only.
Excipient research (literature/general): low-DP chitosan oligomers have been explored as permeability enhancers and mucoadhesive agents in in vitro models; shorter chains (e.g., DP≈10) offer lower viscosity and improved solution handling compared to high-MW chitosan.
Complexation studies: electrostatic complexes with polyanions (e.g., DNA, hyaluronate) are studied to understand charge-driven assembly; oligomers allow better-defined stoichiometry versus polymers.
Stabilization: potential to stabilize proteins or enzymes via weak interactions and crowding effects has been examined in model systems.
Regulatory status: Not specified for this item; no claim of compendial (USP/EP/JP) compliance. Researchers should assess suitability and impurities (e.g., ash, endotoxin) for their specific in vitro models.
Formulation considerations:
Use water as the primary solvent; adjust pH to 4–6 for maximum solubility.
Control ionic strength to tune complexation; chloride from the hydrochloride form contributes to total ionic content.
Filter-sterilize and use promptly to minimize microbial growth; avoid bacteriostats if they interfere with assays.
Physical Properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature: DP≈10 chitooligosaccharide MW commonly ~1.6–2.0 kDa depending on acetylation and salt form.)
Solubility (literature/general):
Highly soluble in water; solubility is enhanced under mildly acidic conditions (e.g., dilute HCl or acetate buffers, pH 4–6) due to amine protonation.
Poorly soluble to insoluble in most aprotic organic solvents (e.g., acetonitrile, ethers, hydrocarbons); limited swelling in alcohol–water mixtures.
pKa (literature/general): apparent pKa of glucosamine C2 amine ~6.3–6.5 in oligomers; chloride salt form exists predominantly as –NH3+ below neutral pH.
Hygroscopicity (literature/general): hygroscopic; can absorb moisture leading to caking and altered mass fraction of water.
Optical rotation (literature/general): chito-oligosaccharides exhibit positive [α]D; value depends on DP and acetylation; not specified for this item.
Thermal behavior (literature/general): non-volatile; decomposes before boiling; thermal softening and caramelization above ~180–200 °C depending on moisture and salt content.
Refractive index, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes:
Prepare aqueous stocks with gentle stirring; avoid high shear that can entrain air.
Filterability improves when fully protonated; use 0.22–0.45 µm membranes (PES or cellulose acetate).
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Identity parameters to expect on CoA (typical for chito-oligosaccharides, literature/general):
Degree of polymerization (DP) distribution (e.g., DP10 predominance or narrow range).
Degree of acetylation (DA) if applicable (chitodecaose often denotes fully deacetylated units; confirm on CoA).
Water content (Karl Fischer) and bioburden/endotoxin where relevant for life science use.
What grade means in practice (general guidance):
Life science/research grade chitooligosaccharides are typically purified to remove low- and high-DP tails, proteins, and colored byproducts, and may be desalinated/dialyzed to defined counterion forms (here: hydrochloride).
For assay-sensitive applications (e.g., receptor-binding or enzyme kinetics), tighter DP distribution and low UV-absorbing impurities are desirable; vendors may specify UV absorbance ratios or HPLC profiles.
Stabilizers/additives:
Not specified for this item; refer to CoA/Spec Sheet. Many carbohydrate salts are supplied without stabilizers; if present (e.g., anti-caking agents), they will be listed on the CoA.
User QC recommendations:
Verify DP profile by HPAEC-PAD or MALDI-TOF.
Confirm solution pH and clarity; filter sterilize if used in cell-based workflows (research use only).
Reaction and Applications
This reagent is primarily used as a defined-length chito‑oligosaccharide standard and functional polysaccharide fragment in life science research.
Research applications (literature/general):
Enzymology: substrate and calibration standard for chitinases/chitosanases; DP-dependent hydrolysis profiling by HPAEC-PAD, LC-MS, or fluorometric assays after labeling.
Glycobiology: ligand for lectins and carbohydrate-binding modules (CBMs) that recognize β-(1→4)-GlcN motifs; investigation of binding affinity as a function of DP.
Plant biology and innate immunity (research use only): elicitor studies of pattern-recognition receptors that sense chitin/chitosan fragments; DP≈6–10 often shows strong activity in certain systems.
Materials/bioconjugation: amine-bearing oligosaccharide for conjugation to dyes, haptens, or carriers via NHS-esters, isothiocyanates, or aldehydes (reductive amination), yielding labeled probes.
Analytical: retention time standards in SEC/HPAEC; calibration of MALDI-TOF for oligosaccharide series.
Practical tips:
For enzyme assays, confirm absence of residual acetylation as it alters chitinase vs chitosanase specificity.
Pre-derivatization (e.g., 2-aminobenzamide, 2-AB; 2-aminobenzoic acid, 2-AA; ANTS) can improve detection; ensure stoichiometric excess of labeling reagent and remove excess by SPE or dialysis.
For binding assays, dialyze or desalt to defined ionic strength; chloride counterions and pH strongly influence electrostatic interactions.
Note: No medical or clinical use is intended; for research use only.
Reaction Conditions
General, literature-based conditions for common transformations of chito‑oligosaccharides; optimize per application.
NHS-ester acylation (amine labeling):
Solvent: aqueous bicarbonate or phosphate buffer, pH 7.8–8.5; minimal organic cosolvent (≤10% DMF/DMSO) to solubilize hydrophobic labels.
Temperature/time: 20–25 °C, 0.5–2 h; protect from light for fluorescent labels.
Stoichiometry: 2–10 equiv label per reactive amine to target low DS; quench with Tris or ethanolamine.
Isothiocyanate labeling (e.g., FITC):
Solvent: carbonate buffer pH 9.0–9.5 with 10–20% DMSO; 4–12 h at RT.
Purification: dialysis (MWCO ~1–3 kDa) or SEC to remove unreacted dye.
Reductive amination at reducing end:
Solvent: acetate buffer pH 5.0–6.0 with label bearing a primary amine; add NaBH3CN (10–50 mM) and react 4–16 h at RT.
Alternative: aniline-catalyzed oxime/hydrazone formation at pH 4.5–5.5 followed by reduction.
Periodate oxidation/crosslinking:
Oxidize in 10–20 mM NaIO4, pH ~5.5, 0–4 °C, 0.5–2 h (protect from light); quench with ethylene glycol; crosslink via hydrazide/amine chemistry.
Enzymatic trimming:
Chitosanases/chitinases under their optimal buffer/pH to tailor DP; monitor by HPLC or MS.
Analytical readouts:
Degree of substitution (DS) by elemental analysis, TNBS/Sulfo‑NHS‑Biotin assays, or UV/fluorometry if chromophores attached.
Maintain aqueous conditions to preserve solubility; avoid strong bases and high temperatures that promote degradation.
Safety and Handling
Authoritative safety information should be taken from the product SDS. The following are general laboratory handling considerations for carbohydrate/oligosaccharide hydrochloride salts.
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
General precautions (literature/practice):
Low inherent toxicity expected for saccharide-based materials, but dust may cause mechanical irritation. Avoid generating dust or aerosols.
The hydrochloride form is acidic in solution; solutions may be mildly corrosive to some metals. Use compatible materials (glass, HDPE, PP, PTFE).
PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use dust mask/respirator if handling large quantities of powder that may aerosolize.
First aid (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Incompatibilities (general): strong oxidizing agents; strong bases may deprotonate and promote Maillard-type browning with carbonyls at elevated temperature; avoid nitrosating agents with primary amines.
Thermal hazards: decomposes on strong heating; avoid drying at high temperatures to prevent discoloration.
Microbial growth: aqueous solutions can support microbial contamination; prepare fresh or add suitable bioburden controls for research use.
Waste disposal: Dispose according to institutional and local regulations for nonhazardous organic aqueous waste unless otherwise specified by the SDS.
Solvent Selection
Chitodecaose hydrochloride is a polar, cationic oligosaccharide; solvent choice focuses on efficient dissolution and compatibility with downstream assays.
Primary solvent: water. Solubility increases under mildly acidic conditions (pH 4–6) as amines remain protonated.
Acidic aqueous media: dilute HCl, HNO3 (careful with metals), or acetate/citrate buffers promote rapid dissolution.
Neutral/alkaline media: solubility may decrease above the apparent amine pKa; dissolution is aided by warming (≤40 °C) and pre-wetting with water.
Organic solvents: generally insoluble in aprotic solvents (ACN, DMSO, DMF) without water. DMSO–water mixtures can dissolve at modest water fractions; pure DMSO dissolubility is limited due to salt character.
Comparison (literature/general):
Chitodecaose·HCl vs free-base chitodecaose: the HCl salt is more water soluble at neutral pH; the free base may require acidification.
Chitodecaose vs chitosan (high-MW): low-DP material dissolves faster, gives lower viscosity at matched w/v %, and filters readily.
Practical guidance:
Target 1–10 mg/mL stocks for biochemical assays; higher concentrations are feasible but increase viscosity.
Add powder slowly to vortexing or stirred water to minimize clumping; allow 10–30 min for complete hydration.
Avoid high-ionic-strength salts if studying electrostatic interactions; chloride from the salt form contributes to ionic strength.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution (literature/general):
Solvent: water or aqueous buffer. For rapid dissolution, adjust solution pH to 4–6 (e.g., acetate buffer) to keep amines protonated.
Concentration: prepare 1–10 mg/mL stocks for most assays; higher concentrations increase viscosity.
Technique: add powder gradually to stirred solvent; allow 10–30 min for full hydration; avoid overheating (>40 °C).
Clarification: filter through 0.22–0.45 µm membranes if required by the application.
Storage of solutions (general):
Short-term: 2–8 °C for up to one week, as microbial growth can occur in carbohydrate solutions.
Long-term: aliquot and store frozen (−20 °C) if permissible for your workflow; thaw gently and mix to redissolve. Avoid repeated freeze–thaw cycles; consider lyophilization to return to solid form.
Sterility: for cell-associated research, prepare under aseptic conditions and consider sterile filtration (research use only).
Stability notes:
Hygroscopic and moisture-sensitive; exposure to humidity can cause caking and mass changes.
Avoid strong bases and prolonged elevated temperatures to minimize browning/degradation.
For exact shelf-life, water content, and any stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Chitodecaose hydrochloride is a chito‑oligosaccharide comprised of approximately ten β-(1→4)-linked D-glucosamine residues (degree of polymerization, DP ≈ 10), with the C2 amino groups protonated and balanced by chloride counterions.
SKU: C305409
Product name: Chitodecaose hydrochloride
CAS: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
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. (Note: for DP≈10, the average MW is typically in the low kDa range, literature.)
Structural features (literature/general):
Repeating unit: β-D-GlcN (2-amino-2-deoxy-D-glucopyranose) linked via β-(1→4) glycosidic bonds.
Functional groups: multiple primary/secondary hydroxyls; protonated primary amines (–NH3+) at C2 as hydrochloride salt; acetal/hemiketal ring oxygens; glycosidic oxygens.
Stereochemistry: each residue is D-glucopyranose with defined stereocenters; all linkages β-anomeric.
2D description: linear oligosaccharide chain of ~10 hexose rings connected head-to-tail via O-glycosidic bonds; pendant OH groups project equatorially/axially per glucopyranose chair; each C2 bears –NH3+·Cl− in the salt form.
Notes on identity: Chitodecaose often denotes a narrowly distributed DP≈10 fraction of chito-oligosaccharides. Exact DP distribution, degree of acetylation (if any), and counterion content should be confirmed from the item’s CoA/Spec Sheet.
Synthetic Utility
Although not a classical small-molecule building block, chitodecaose·HCl offers versatile functional handles for conjugation and derivatization in carbohydrate and materials chemistry (literature/general):
Primary amines (C2 on each residue):
Amide formation with activated esters (NHS-esters) under mildly basic conditions (pH 7.5–8.5) when temporarily converted to the free-base; for HCl salt, pre-neutralization is required.
Urea/thiourea formation via isocyanate/isothiocyanate reagents (e.g., fluorescein isothiocyanate labeling).
Reductive amination with aldehydes/ketones using NaBH3CN or picoline borane to install linkers or tags.
Reducing end aldehyde: present at one chain terminus (in equilibrium with cyclic hemiacetal) enabling:
Reductive amination with amines for end-specific labeling.
Oxime/hydrazone ligation with alkoxyamines/hydrazides; subsequent reduction for stability.
Hydroxyl groups: periodate oxidation (vicinal diols) to dialdehydes followed by crosslinking; carbonate/carbamate formation; silylation/acylation for protection strategies.
Glycan display: multivalent presentation on nanoparticles, proteins, or surfaces via bifunctional linkers to interrogate lectin/CBM binding.
Practical notes:
Control substitution degree to preserve aqueous solubility and avoid extensive crosslinking.
For site-selective end-labeling, cap internal amines (e.g., transient protection) or exploit the unique reactivity of the reducing end.
Purify conjugates by dialysis/SEC to remove small-molecule reagents; confirm DP and modification by MALDI-TOF or LC-MS where ionization allows.
Target Specificity
Not applicable. This product is a carbohydrate reagent, not an antibody or affinity reagent with defined antigen/epitope specificity. For binding studies to lectins or receptors, consult primary literature for the specific protein of interest and characterize interactions empirically (e.g., ITC, SPR, BLI).
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