Turanose, d- , CAS No.5460935

CAS: 5460935 Cat. No.: T1039022 Formula: C₁₂H₂₂O₁₁ Peso molecolare: 342.300 Numero EC: EINECS208-918-5

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]([C@@H]([C@@H](CO)O)O)C(=O)CO)O)O)O)O

IUPAC Name

(3S,4R,5R)-1,4,5,6-tetrahydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one

InChIKey

RULSWEULPANCDV-PIXUTMIVSA-N

INCHI

1S/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1

Peso molecolare

342.300

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acyl glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acyl glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acyl glycosides of mono- and disaccharides
• Alternative Parents: Alkyl glycosides O-glycosyl compounds Disaccharides Fatty alcohols Oxanes Beta-hydroxy ketones Alpha-hydroxy ketones Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Fatty acyl glycoside of mono- or disaccharide - Alkyl glycoside - Disaccharide - Glycosyl compound - O-glycosyl compound - Fatty alcohol - Beta-hydroxy ketone - Oxane - Alpha-hydroxy ketone - Secondary alcohol - Ketone - Acetal - Organoheterocyclic compound - Oxacycle - Polyol - Alcohol - Primary alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Aliphatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
• External Descriptors: glycosylfructose

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

Proprietà chimiche e fisiche

• Peso molecolare: 342.300 g/mol
• XLogP3: -4.800
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 342.116 Da
• Monoisotopic Mass: 342.116 Da
• Topological Polar Surface Area: 197.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 378.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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 item-specific tested application protocols are provided for this SKU. The following are general, literature-based preparation guidelines for research use:

• Stock solution preparation (aqueous):

  • Weigh desired amount quickly to minimize ambient moisture uptake.
  • Add to ~80% of the final volume of ultrapure water; stir at RT with gentle warming (≤40–45°C) until fully dissolved.
  • Adjust pH if required (typically near neutral). Bring to volume. Filter-sterilize (0.22 µm) for sterile work.
  • Typical working concentrations: 0.1–10% w/v for stabilization/osmotic studies; 1–100 mM for biochemical assays. Optimize per application.

• Plant assay example (conceptual):

  • Prepare matched solutions of turanose and sucrose at equal molarity in growth medium.
  • Treat seedlings under identical conditions and quantify phenotypic or transcriptomic responses linked to sugar signaling. Confirm concentrations do not cause osmotic stress artifacts.

• Analytical calibration:

  • Generate calibration curves by HPLC-RI or HPAE-PAD using known standards of turanose and potential isomers (sucrose, palatinose) for resolution.

These are general guidelines and not validated protocols for this product. Verify compatibility with your system and consult primary literature.

Biological Roles

Scope: Research-use context only. No clinical/therapeutic claims.

Literature-based roles and observations:

• Plant sugar signaling: D-Turanose is widely used as a sucrose analog to dissect sugar sensing/transport. Its uptake and metabolism differ from sucrose, enabling differentiation between signaling and nutritional effects in Arabidopsis and other species.
• Carbon source: Functions as a fermentable/reducible sugar in some microbes; however, transporters/enzymes may recognize it with different affinities vs sucrose, glucose, or fructose.
• Reducing sugar chemistry: With a free anomeric center on the fructose unit, turanose participates in typical reducing sugar reactions (e.g., formation of Schiff bases with amines under appropriate conditions), which may influence protein stability in complex matrices.
• Osmotic and stabilizing effects: Like other disaccharides, contributes to osmotic balance; in vitro, can stabilize macromolecules by preferential exclusion and water-structuring effects.

Experimental considerations:

• Enzymatic susceptibility: Glycosidases that act on sucrose may not cleave turanose efficiently; verify enzyme specificity in your system.
• Transport specificity: If probing transporter function, pair turanose with controls (sucrose, palatinose, trehalose) and quantify uptake/metabolic flux.
• Analytical detection: Use HPLC-RI, HPAE-PAD, or LC-MS (derivatized) to separate turanose from isomeric disaccharides.

Buffer Applications

D-Turanose is not a buffering agent. It does not provide significant acid–base capacity in the physiological pH range.

Relevant roles in buffered systems (literature/practice):

• Additive for stabilization: Inclusion at 1–20% w/v ranges is commonly screened to enhance protein/enzyme stability via preferential hydration; optimize concentration to balance viscosity and activity.
• Osmotic control: Adjust osmolality in biological assays; compute osmolality based on complete or partial dissociation (sugars are non-electrolytes). Disaccharides contribute approximately 1 osmol per mole when fully in solution.
• Avoid Maillard chemistry: In buffers containing primary amines (e.g., Tris, glycine, Lys-rich proteins), reducing sugars can form adducts upon heating/long storage. Keep solutions cool, freshly prepared, and avoid prolonged high-temperature exposure.

Preparation tips:

• Dissolve directly in water or buffer with gentle warming (<40–45°C) and stirring.
• Filter-sterilize through 0.22 µm membranes if sterility is required.
• Record exact concentration by mass and final volume; check refractive index or density if high precision is essential.

Green Alternatives

Context: As a benign, bio-based carbohydrate, D-turanose itself is generally considered low-hazard and renewable. “Green alternatives” most relevantly compare to other saccharides chosen for functional equivalence.

Comparison (literature/general):

• Versus sucrose:

  • Pros for turanose: Reducing functionality can be advantageous in certain conjugations or signaling studies; may be sensed/transported differently in plant systems.
  • Pros for sucrose: Nonreducing (greater stability against Maillard-type reactions), widely available food/pharma grades at scale.

• Versus glucose or fructose:

  • Pros for turanose: Distinct uptake/metabolism profiles allow differential biological probing.
  • Pros for monosaccharides: Lower molecular complexity; simpler quantitation and often higher diffusivity.

• Environmental considerations:

  • All options are bio-based and biodegradable; selection should emphasize minimal processing, available certifications (if needed), and avoidance of unnecessary organic co-solvents.

Practical guidance: If your goal is merely osmotic adjustment or innocuous bulking, sucrose or glucose may be greener from a supply-chain and cost perspective. If the experimental design hinges on sucrose signaling decoupled from full metabolism, turanose can be the fit-for-purpose choice, reducing repeat experiments and waste.

Pharmaceutical Uses

This listing is for research use only (per Product Data). No pharmacopeial or clinical use is implied.

General formulation context (literature/practice, not item-specific):

• Excipients: Disaccharides are frequently used as stabilizers/lyoprotectants and bulking agents in parenteral and solid-dose formulations; specific adoption of turanose would require appropriate excipient qualification and regulatory documentation.
• Reducing character: Turanose is a reducing sugar; for pharmaceutical formulations, this can be a liability due to potential Maillard reactions with amine-containing actives or excipients. Nonreducing alternatives (e.g., sucrose, trehalose) are preferred when applicable.
• Analytical control: If considered for preformulation screening, assess reducing sugar content, impurity profile (e.g., monosaccharides), water content, and microbial limits.

Compliance note: No grade, purity, or pharmacopeial status is specified for this item. For any application beyond basic research, a qualified grade (e.g., USP/NF, Ph.Eur.) and full excipient dossier would be required.

Physical Properties

Item-specific specifications (for this catalog entry):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight (Product Data): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for D-turanose (for reference only; not item-specific):

• Molecular formula: C12H22O11 (literature)
• Molecular weight: ~342.30 g/mol (literature)
• Physical state: crystalline solid; strongly hygroscopic tendencies are common for disaccharides (literature, general for sugars).
• Solubility: highly soluble in water; insoluble or very sparingly soluble in nonpolar organic solvents (literature, general behavior of disaccharides).
• Taste: sweet (literature; sensory property, not a specification for lab use).
• Thermal behavior: like many sugars, softening and decomposition can occur upon heating; precise melting/decomposition temperature for turanose is variably reported and method-dependent (literature). Use DSC/TGA if critical.
• Optical activity: D-sugar; a positive specific rotation is expected, but the exact [α]D value varies by conditions and source. Consult primary literature or CoA for numeric value.

Note: When using any literature values operationally, validate in-house or consult the Certificate of Analysis/Spec Sheet for this lot. Do not treat literature values as specifications.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and considerations (general guidance for professional users):

• If an assay value (e.g., ≥98% by HPLC/GC) is critical for your application (enzymology, plant signaling assays, crystallization), request and review the CoA for this lot. Sugars can contain moisture and trace inorganic content that influence mass balance and solution osmolality.
• UV profile/absorbance: Disaccharides typically have no strong absorbance above 220–230 nm. If using in HPLC mobile phases or spectroscopic assays, ensure low-UV impurities are controlled (HPLC/UV-grade concept; not specified for this item).
• Microbial/bioburden: If sterile or low-bioburden material is required (cell culture/osmotic studies), check for microbiological specifications on the CoA or perform sterile filtration of solutions.
• Stabilizers/additives: Not anticipated for neat carbohydrates; nonetheless, confirm “additive-free” status on CoA if required. Any stabilizers present would be item-specific; none are specified here.

Documentation: For metrological traceability (assay, water content by Karl Fischer, ash content, metals), consult the CoA/Spec Sheet. Values are not specified for this catalog entry.

Reaction and Applications

This product is primarily used as a biochemical/plant-physiology probe and as a carbohydrate building block rather than as a general organic solvent or reagent.

• Research uses (literature, expanded):

  • Sugar signaling studies: D-Turanose is a sucrose isomer that is often transported or sensed differently; used to dissect sucrose-specific signaling in plants (e.g., Arabidopsis). Because it is a reducing disaccharide, it may engage differently with transporters/enzymes compared to sucrose.
  • Carbon source/osmolyte: Employed as a defined carbon source in microbial or plant tissue culture experiments to probe metabolism and osmotic responses.
  • Stabilizing additive: Carbohydrates can stabilize proteins/enzymes by preferential hydration; turanose solutions may be screened during formulation-like studies.

• Synthetic/chemical applications (literature):

  • Carbohydrate derivatization: Acylation (acetylation, benzoylation), etherification (benzylation), and selective protection strategies on polyols.
  • Glycosylation chemistry: With appropriate protection, turanose-derived fragments can be transformed into glycosyl donors/acceptors for oligosaccharide synthesis.

• Practical tips:

  • Drying: Sugars are hygroscopic; if exact mass fraction is critical, determine water content by Karl Fischer on your lot (consult CoA if available). Drying under vacuum at mild temperature can reduce surface moisture.
  • Purity checks: 1H/13C NMR in D2O and HPAE-PAD or HPLC-RI are commonly used for characterization; reducing sugars may show anomeric equilibration in solution.
  • Avoid strong acid/base during prolonged heating to prevent hydrolysis and degradation.

Reaction Conditions

General, literature-based guidance for common carbohydrate transformations involving reducing disaccharides like turanose. These are not specifications for this item; optimize per system.

• Per-O-acetylation: Ac2O (excess), pyridine or DMAP catalysis, 0–25°C, 2–12 h. Workup by quench with MeOH/H2O, extract, and purify by chromatography.

• Benzylation: BnBr (2–6 equiv), NaH or Ag2O, DMF or toluene, 0–25°C then warm to 60–80°C as needed, 4–24 h. Ensure rigorous drying to avoid base quench by water.

• Silylation: TBSCl (2–6 equiv), imidazole, DMF, 0–25°C, 2–6 h. Protect from moisture; monitor by TLC with anisaldehyde stain.

• Reductive amination (on reducing end): Amine (1–5 equiv), NaBH3CN or picoline borane, MeOH/AcOH or aqueous buffer pH 5–6, 20–40°C, 2–24 h. Control pH to balance imine formation and reductant stability.

• Glycosyl donor formation (example): Trichloroacetimidate formation using CCl3CN and base (e.g., DBU) on suitably protected hemiacetal, 0°C to RT, 1–3 h; subsequent glycosylation promoted by TMSOTf at −78 to 0°C.

• Analytical and workup tips:

  • Sugars are polar; normal-phase silica may require moderately polar eluents (EtOAc/hexane to EtOAc/MeOH) or resort to reverse-phase or HILIC methods.
  • Use azeotropic drying (toluene co-evaporation) before moisture-sensitive steps.
  • Monitor by TLC with carbohydrate stains (anisaldehyde, p-anisidine–phosphoric acid) or HPLC-RI.

Note: Carbohydrate reactions are sensitive to subtle stereoelectronic effects. Small-scale scouting experiments are recommended to refine catalysts/loadings/temperatures.

Safety and Handling

Authoritative source: Always consult the SDS for this SKU before use.

• GHS classification (this item): Not specified for this item; refer to SDS. Disaccharides like turanose are generally considered of low acute toxicity; however, classification depends on supplier data.
• Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for carbohydrates (literature/good practice):

• Hazards: May cause mild eye/skin/respiratory irritation as dust. Combustible dust hazard is possible if fine particulates become airborne in sufficient concentration with an ignition source.
• PPE: Lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use dust mask or local exhaust if handling powders prone to aerosolization.
• Handling: Avoid generating dust clouds. Use clean, dry tools. Prevent contamination with moisture (lumping/stickiness) and with strong oxidizers.
• Incompatibilities: Strong oxidizing agents; strong acids/bases can promote hydrolysis/caramelization upon heating.
• First aid (general): Rinse eyes/skin with water if contacted. Move to fresh air if inhaled dust causes irritation. If ingested in the lab, rinse mouth; seek medical attention according to institutional policy and SDS guidance.
• Fire-fighting: Use water spray, CO2, dry chemical. Dust explosions are a general risk for organic powders; minimize dust accumulation.

Storage per Product Data: Room temperature. Store tightly closed in a dry area away from strong oxidizers and ignition sources. Consult SDS for shelf-life and additional details.

Solvent Selection

Applicability: D-Turanose is a solid carbohydrate; solvent choice concerns dissolution for use, not extraction as an organic reagent.

• Polarity and miscibility (literature/general):

  • Highly polar; forms extensive hydrogen-bond networks.
  • Freely soluble in water; solubility increases with temperature.
  • Poorly soluble in alcohols beyond methanol/ethanol (limited), and effectively insoluble in nonpolar solvents (e.g., hexanes, toluene).

• Practical solvent guidance:

  • Aqueous solutions (buffered or unbuffered) are standard for biochemical and plant-physiology applications. Adjust pH neutrality (pH 6–7.5) to minimize hydrolysis/isomerization during extended incubations.
  • For sterile applications, prepare in ultrapure water and 0.22 µm filter-sterilize. Avoid autoclaving concentrated sugar solutions due to caramelization/maillard-type degradation in presence of amino compounds.
  • Co-solvents: Small fractions of ethanol or methanol may be used to assist wetting but can reduce stability of biological systems; validate compatibility.

• Comparison (literature):

  • Versus sucrose: Similar aqueous solubility; turanose is reducing, whereas sucrose is nonreducing.
  • Versus glucose/fructose: Disaccharide solutions provide different osmolality-to-mass ratios; turanose may exhibit altered uptake/metabolism in specific biological systems.

Storage and Reconstitution

• Storage conditions (Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general):

• Keep container tightly closed in a cool, dry place. Protect from humidity to prevent caking and microbial growth in opened containers.
• If long-term storage is planned, consider desiccator storage with a suitable desiccant. Record opening date and lot number.
• Avoid cross-contamination; use clean, dry spatulas.

Reconstitution/solution handling (general):

• Prepare solutions in freshly produced ultrapure water. For sterile applications, filter-sterilize through 0.22 µm membranes. Avoid autoclaving concentrated solutions to prevent sugar degradation.
• Solution storage: For short term, 2–8°C protected from light; for longer term, aliquot and freeze at −20°C to minimize microbial growth and degradation. Minimize freeze–thaw cycles.
• Concentration verification: For precise work, verify concentration gravimetrically and/or by refractive index or HPLC-RI.

Unspecified parameters: Any item-specific stabilizers, residual moisture content, metals, or UV cutoffs are not specified for this item; refer to CoA/Spec Sheet and SDS for authoritative details.

Structure and Identity

Brief overview: D-Turanose is a reducing disaccharide consisting of D-glucose and D-fructose linked through an α-D-glucopyranosyl-(1→3)-D-fructofuranose bond (literature). It is a structural isomer of sucrose with the same gross composition but different connectivity.

• Product Data specifics (as provided for this item):

  • CAS: 5460935 (as listed in Product Data)
  • CID: 5460935 (as listed in Product Data)
  • InChIKey: 326358 (truncated/atypical format as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general reference values, not item-specific specifications):

  • Common name: D-Turanose
  • Molecular formula: C12H22O11 (literature; typical for disaccharides isomeric with sucrose)
  • Molecular weight: ~342.30 g/mol (literature)
  • Preferred IUPAC name (literature): α-D-glucopyranosyl-(1→3)-D-fructofuranose

• Structural features (literature):

  • Two monosaccharide rings: one six-membered α-D-glucopyranose and one five-membered D-fructofuranose.
  • Glycosidic linkage: C1 of glucose (α) to C3 of fructose (1→3 linkage).
  • Numerous secondary alcohols (polyhydroxy functionality), one free anomeric center on the fructose unit → reducing sugar behavior.
  • Stereochemistry: multiple defined chiral centers consistent with D-configurations of constituent monosaccharides.

• 2D description in words (literature): A chair-form glucopyranose bearing an axial anomeric linkage projects to an attached fructofuranose ring; each ring is decorated with hydroxyl groups in the canonical orientation for D-glucose and D-fructose, respectively.

Synthetic Utility

From an organic synthesis perspective (literature/general), D-turanose is a densely functionalized polyol and reducing disaccharide, offering multiple entry points for derivatization:

• Protection strategies: Selective protection of hydroxyl groups via acylation (Ac2O/pyridine), silylation (TBDMS/TBSCl, imidazole), benzylation (BnBr/NaH), enabling site-specific transformations. Neighboring group effects from acyl protections can steer later glycosylations.
• Glycosyl donor/acceptor preparation: Conversion of the free anomeric center on the fructofuranose to donors (e.g., trichloroacetimidates, thioglycosides) after appropriate protection, allowing assembly of tailored oligosaccharides.
• Oxidation/reduction: Periodate oxidation (on vicinal diols) for cleavage/mapping; TEMPO-mediated selective oxidation of primary alcohols to acids; NaBH4/cyanoborohydride for reductive amination with amines (exploiting reducing end).
• Conjugation chemistry: Reductive amination to couple with amines forming glycosylamines; carbamate/urethane linkages after activation; click-type strategies after installing azido/alkynyl handles onto selectively activated hydroxyls.

Practical notes:

• Anomeric equilibria: In solution, reducing end may exist as a mixture of anomers; control conditions to favor desired form.
• Analysis: Detailed 2D NMR (COSY, HSQC, HMBC, NOESY) is invaluable for regiochemical and stereochemical assignment post-derivatization.
• Protecting-group economy: Carbohydrate synthesis benefits from orthogonal protection; plan routes minimizing protecting group manipulation to maintain yields.

Target Specificity

Not applicable. This product is a small-molecule carbohydrate, not an antibody, enzyme, or affinity reagent. No target, epitope, or species reactivity is defined for D-turanose. For biochemical context on transporter/enzyme specificity, see the Biological Roles section.