Udp-Glucose (133-89-1) Physical and Chemical Properties
Udp-Glucose
Activated nucleotide sugar (uridine diphosphate glucose) supplied as a solid biochemical intermediate for enzymatic glycosylation reactions, metabolic research and reagent-grade applications.
| CAS Number | 133-89-1 |
| Family | Nucleotide sugars |
| Typical Form | Powder or crystalline solid |
| Common Grades | EP, FCC |
Uridine diphosphate glucose (UDP‑glucose) is a nucleotide sugar belonging to the uridine-diphosphate family of activated glycosyl donors. Structurally it is a uridine nucleoside linked via a diphosphate bridge to a glucopyranosyl unit; the isolated neutral covalent formula is \(\ce{C15H24N2O17P2}\). Key electronic features include multiple hydroxyls on the sugar moiety, two phosphate groups capable of ionization, and a pyrimidine base (uridine) that provides aromatic character and hydrogen‑bonding sites. The molecule contains multiple stereocenters (defined atom stereocenter count 9) and high topological polar surface area, consistent with strong hydration and extensive polar interactions with proteins and aqueous media.
Because of its two phosphoric acid residues and several hydroxyl functionalities, UDP‑glucose is highly hydrophilic and displays very low partitioning into nonpolar phases; the computed XLogP3 is -6.3. In biological milieu it exists predominantly in ionized forms (biochemically described as related to UDP‑alpha‑D‑glucose(2-)), and its ionic character underlies tight, specific binding in enzyme active sites (glycosyltransferases, epimerases). The compound is labile to enzymatic turnover (glycosyl transfer, epimerization, pyrophosphatase activity) and is more resistant to nonenzymatic hydrolysis at neutral pH than simple esters, although alkaline conditions and elevated temperatures accelerate phosphate cleavage and glycosidic bond breakdown.
As a central metabolite, UDP‑glucose is industrially and pharmaceutically relevant primarily in research and production contexts (glycobiology, enzymology, metabolic assays). It functions as the activated glucosyl donor in glycogen and polysaccharide biosynthesis and is used as a reagent or standard in analytical laboratories studying nucleotide‑sugar metabolism. Common commercial grades reported for this substance include: EP, FCC.
Molecular Overview
Molecular Weight and Composition
- Molecular formula (covalent unit): \(\ce{C15H24N2O17P2}\).
- Molecular weight: 566.30 (reported value). The conventional unit for molar mass is \(\mathrm{g}\,\mathrm{mol}^{-1}\).
- Exact mass / Monoisotopic mass: 566.05502130 (reported).
- Heavy atom count: 36.
- Complexity: 964 (computed descriptor).
- Defined atom stereocenter count: 9.
These descriptors reflect a relatively large, highly functionalized polar molecule with multiple stereocenters typical of nucleotide sugars; the high complexity and stereocenter count are important for stereospecific enzyme recognition.
Charge, Polarity, and LogP
- Computed XLogP3: -6.3 (reported).
- Formal charge (computed): 0 (neutral covalent representation in the isolated compound).
- Hydrogen bond donors: 9 (reported).
- Hydrogen bond acceptors: 17 (reported).
- Topological polar surface area (TPSA): 292 (reported; unit conventionally \(\mathrm{\AA}^2\)).
The negative XLogP and large TPSA indicate extreme hydrophilicity and strong solvation in aqueous environments. In vivo and in enzyme complexes the diphosphate moiety is typically ionized, which increases net negative charge and promotes interactions with positively charged protein residues and divalent metal cofactors in active sites.
Biochemical Classification
UDP‑glucose is classified as a nucleotide sugar (uridine diphosphate sugar). Functionally it serves as an activated glycosyl donor and a central metabolite in carbohydrate metabolism. It is a precursor for glycogen synthesis and is enzymatically converted to other nucleotide sugars (for example UDP‑galactose and UDP‑glucuronic acid) that are incorporated into polysaccharides, glycosphingolipids, lipopolysaccharides and other glycoconjugates.
Chemical Behavior
Stability and Degradation
UDP‑glucose commonly occurs as a solid in isolated preparations (physical description: Solid). As a class, nucleotide sugars are chemically stable under mild, neutral aqueous conditions but are susceptible to cleavage of the diphosphate linkage under strongly alkaline conditions or at elevated temperatures. Enzymatic mechanisms (pyrophosphatases, nucleotidases) rapidly degrade the diphosphate linkage under physiological conditions when catalyzed, and glycosyltransferases consume UDP‑glucose by transferring the glucosyl moiety to acceptor substrates. Nonenzymatic oxidative degradation of the sugar or base is not a dominant pathway under standard storage conditions but may occur under prolonged exposure to oxidants or light.
Experimental collision cross section (CCS) values determined by ion mobility show reproducible gas-phase conformational characteristics for ionic adducts; representative reported CCS entries include: "209.2 Å^2 [M+Na]+", "207.5 Å^2 [M-H]-", and a set of related measurements in the 207–216 Å^2 range for various adducts and calibrations. These MS‑IMS data reflect the molecule’s extended, highly solvated conformations upon desolvation.
Hydrolysis and Transformations
- Enzymatic interconversions: UDP‑glucose is converted enzymatically into UDP‑galactose and UDP‑glucuronic acid, and it serves as substrate for glycosyltransferases that attach glucose to growing polysaccharide or glycoconjugate chains. These transformations are central to its metabolic role.
- Nonenzymatic hydrolysis: No specific kinetic constants are provided in the current data context. General behavior for nucleotide diphosphate sugars is accelerated hydrolysis at elevated pH and temperature; in practice, solutions are buffered and kept cold to minimize nonenzymatic breakdown.
If numerical acid–base dissociation constants (pKa values) for the phosphoric acid groups are required, no experimentally established values for these constants are available in the current data context.
Biological Role
Functional Role and Pathways
UDP‑glucose functions as an activated glucosyl donor in multiple biosynthetic processes:
- Precursor of glycogen synthesis (glycogen biosynthesis uses UDP‑glucose as the immediate donor for glucosyl transfer).
- Metabolic precursor to UDP‑galactose and UDP‑glucuronic acid, which feed into galactose metabolism and into biosynthesis of glucuronides and structural polysaccharides.
- Donor substrate for biosynthesis of sucrose, bacterial lipopolysaccharides, glycosphingolipids and other glycoconjugates.
Pathway annotations associated with UDP‑glucose include galactose metabolism, glycogen metabolism and multiple glycosylation pathways; the available data list specific pathway associations such as galactose metabolism and a broader set of 21 pathways referenced in pathway annotations.
Physiological and Cellular Context
- Tissue locations reported: Liver; Skeletal Muscle.
- Cellular locations reported: Endoplasmic reticulum; Golgi apparatus.
These locations are consistent with the molecule’s roles in glycogen synthesis (muscle, liver) and glycosylation processes that occur within the secretory pathway (ER and Golgi). UDP‑glucose participates in enzyme‑mediated transfer reactions localized to these compartments and is a ubiquitous metabolite across diverse organisms.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS Registry Number: 133-89-1
- European Community (EC) number: 205-121-4
- UNII: V50K1D7P4Y
- ChEBI: CHEBI:46229
- ChEMBL: CHEMBL375951
- DrugBank: DB01861
- HMDB: HMDB0000286
- KEGG: C00029
Other registry and database identifiers appear in the data set; the CAS number above is provided exactly as reported.
Synonyms and Biological Names
Common synonyms (as reported) include: Uridine Diphosphate Glucose; UDP Glucose; UDPG; Uridine Diphosphoglucose; UDP‑Glc; Uridine 5'‑diphosphoglucose. Additional depositor-supplied synonyms and systematic names are available for biochemical and analytical use.
Identifiers for structural descriptors (provided values):
- SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O)O)O
- InChI: InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
- InChIKey: HSCJRCZFDFQWRP-JZMIEXBBSA-N
All structural and registry identifiers above are reported values for the molecule.
Safety and Handling Overview
Handling and Storage of Biochemical Materials
UDP‑glucose is supplied and handled as a polar, nonvolatile solid or as aqueous solutions in laboratory and research settings. General precautions appropriate for biochemical reagents should be applied: use of suitable personal protective equipment (gloves, eye protection, lab coat), control of dust during weighing, and avoidance of ingestion and inhalation. Because nucleotide sugars are prone to enzymatic and nonenzymatic degradation, store samples under conditions that minimize hydrolysis and microbial contamination (dry, protected from prolonged light exposure, and refrigerated or frozen as recommended by the supplier). Prepare solutions in appropriate buffers and minimize freeze–thaw cycles for long-term stability.
For waste disposal, spill response, and detailed hazard, transport and regulatory information, users should refer to the product‑specific Safety Data Sheet (SDS) and to applicable local legislation.
