80876-59-1

Basic information

• Product Name: L-Idaric-1,4-lactone
• Synonyms: L-Idaric-1,4-lactone;L-Idaric acid 1,4-lactone
• CAS NO: 80876-59-1
• Molecular Formula: C₆H₈O₇
• Molecular Weight: 208.121
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Inhibitors
• Mol File: 80876-59-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 145-147°C
• Boiling Point: 537.568°C at 760 mmHg
• Flash Point: 230.054°C
• Appearance: /
• Density: 1.961g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: 3.28±0.11(Predicted)
• CAS DataBase Reference: L-Idaric-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-Idaric-1,4-lactone(80876-59-1)
• EPA Substance Registry System: L-Idaric-1,4-lactone(80876-59-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 80876-59-1(Hazardous Substances Data)

Usage

Description

L-Idaric-1,4-lactone is a white to off-white solid that acts as an inhibitor of α-L-idosidase, an enzyme involved in the metabolism of glycoproteins and glycolipids.

Uses

Used in Pharmaceutical Industry:
L-Idaric-1,4-lactone is used as an inhibitor of α-L-idosidase for its potential therapeutic applications in treating lysosomal storage disorders, such as I-cell disease and mucopolysaccharidoses, by modulating the activity of the enzyme and improving the clearance of accumulated substrates.
Used in Research Applications:
L-Idaric-1,4-lactone serves as a valuable research tool in biochemical and cell biology studies, where it can be employed to investigate the role of α-L-idosidase in various biological processes and its potential as a target for drug development.

InChI:InChI=1/C6H8O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11/h1-4,7-9H,(H,10,11)/t1-,2-,3?,4-/m0/s1

Upstream product

• 4539-77-9 2,4:3,5-di-O-methylene-D-glucaric acid dimethyl ester 
• 7437-69-6 2,4:3,5-di-O-methylene-L-idaric acid 
• 526-99-8 meso-galactaric acid 
• 527-00-4 allo-mucic acid 
• 685-73-4 D-galacturonic acid 

Downstream Products

• 47173-55-7 galactaric acid mono-(N'-phenyl-hydrazide) 

Relevant articles and documents

Crystal structure of uronate dehydrogenase from Agrobacterium tumefaciens

Uronate dehydrogenase from Agrobacterium tumefaciens (AtUdh) belongs to the short-chain dehydrogenase/reductase superfamily and catalyzes the oxidation of D-galacturonic acid and D-glucuronic acid with NAD+ as a cofactor. We have determined the crystal structures of an apo-form of AtUdh, a ternary form in complex with NADH and product (substrate-soaked structure), and an inactive Y136A mutant in complex with NAD+. The crystal structures suggest AtUdh to be a homohexamer, which has also been observed to be the major form in solution. The monomer contains a Rossmann fold, essential for nucleotide binding and a common feature of the short-chain dehydrogenase/reductase family enzymes. The ternary complex structure reveals a product, D-galactaro-1,5-lactone, which is bound above the nicotinamide ring. This product rearranges in solution to D-galactaro-1,4-lactone as verified by mass spectrometry analysis, which agrees with our previous NMR study. The crystal structure of the mutant with the catalytic residue Tyr-136 substituted with alanine shows changes in the position of Ile-74 and Ser-75. This probably altered the binding of the nicotinamide end of NAD+, which was not visible in the electron density map. The structures presented provide novel insights into cofactor and substrate binding and the reaction mechanism of AtUdh. This information can be applied to the design of efficient microbial conversion of D-galacturonic acid-based waste materials.