2-Deoxy-D-ribonic acid-1,4-lactone

2-Deoxy-D-ribonic acid-1,4-lactone is a chemically synthesized sugar acid lactone derived from 2-deoxy-D-ribonic acid. It features a five-membered lactone ring formed by the intramolecular esterification between the terminal hydroxyl and carboxylic acid groups. This compound is significant in biochemical and organic synthesis research, serving as a molecular building block and an inhibitor in metabolic studies. It plays a role in studies related to carbohydrate metabolism and enzymatic activity involving sugar acids. Due to its unique structure—lacking a hydroxyl group at the 2-position—it is utilized as a probe in mechanistic enzymology and pharmaceutical research. The lactone form provides stability and distinct biochemical properties compared to the open-chain acid. It is available in high purity and used extensively for biochemical assay development and structural studies.

IUPAC Name

• (4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
• Also referred to as 2-Deoxy-D-ribono-1,4-lactone or 2′-deoxyribonolactone

Appearance

• White to off-white powder or crystalline solid

Source

• Synthetic chemical made via selective oxidation and lactonization of 2-deoxy-D-ribonic acid or related sugar precursors

Molecular Weight and Structure

• Molecular formula: C5H8O4
• Molecular weight: 132.11 g/mol
• Structure: Gamma-lactone ring (five-membered dihydrofuranone) with hydroxyl and hydroxymethyl substituents, lacking a 2-hydroxyl group
• SMILES: C(O)[C@@H]1C@@HCC(=O)O1

Sugar Specificity

• Derivative of 2-deoxy sugar acids related to D-ribonic acid family
• Lacks hydroxyl at C2, making it a specific analog used for probing sugar acid metabolism and enzymatic mechanisms involving deoxy sugars

Biological Activity

• Used as an irreversible inhibitor of DNA polymerase in biochemical studies
• Employed as a molecular tool in enzymology and organic synthesis
• Acts in various biochemical pathways involving sugar acid metabolism
• Its biochemical role in herbs and spices as a minor metabolite is reported but not fully elucidated

Purity and Microbial Contamination

• Purity generally ≥95-99% depending on supplier and grade ([GC]-gas chromatography verified)
• Microbial contamination not typically applicable due to synthetic pharmaceutical grade production
• Supplied with certificates of analysis and high purity standards

Identity and Quality Control

• Verified with NMR, mass spectrometry, and chromatographic techniques
• Structural confirmation via InChI, SMILES, and molecular formula
• Certificate of Analysis provided with each batch
• Quality control standards include melting point analysis and spectral verification

Shelf Life and Storage

• Stable for 2–3 years under appropriate storage
• Store at low temperatures (preferably -20°C for long term) in a dry, light-protected environment
• Avoid moisture and repeated freeze-thaw cycles
• Supplied typically as lyophilized powder to maximize stability

Application

• Molecular tool for enzymology and study of sugar metabolism
• Used in DNA polymerase inhibition research and biochemical assay design
• Intermediate in organic synthesis of sugar acid derivatives
• Employed in biochemical research to mimic or block natural sugar acid metabolic pathways
• Valuable for carbohydrate chemistry and metabolic pathway elucidation studies

Key Characteristics

• Synthetic sugar acid lactone with molecular weight 132.11 g/mol
• CAS number: 34371-14-7
• White powder, high purity ≥95–99%
• Five-membered gamma-lactone with hydroxyl and hydroxymethyl groups
• Inhibitor in biochemical studies, especially DNA polymerase activity
• Stable under refrigerated or frozen storage conditions
• Applied in enzymology, organic synthesis, and carbohydrate metabolism research
• Molecular probe for sugar acid pathways
• Supplied with strong quality control and identity verification
• Used in pharmaceutical and biochemistry laboratories globally

Citation 

• Glentham 2-Deoxy-D-ribonic acid-1,4-lactone
• Circa Group chemical info
• ChemicalBook detailed datasheet
• LookChem product listing
• PubChem 2-Deoxy-l-ribono-1,4-lactone
• J-GLOBAL chemical substance info
• TargetMol catalog
• Molecular Depot product description
• BlueTiger Scientific biochemical grade
• Biogen product and shipping details