82206-03-9

Basic information

• Product Name: beta-D-Glucopyranuronic acid, 1-(1,1'-biphenyl)-4-carboxylate
• Synonyms: beta-D-Glucopyranuronic acid, 1-(1,1'-biphenyl)-4-carboxylate
• CAS NO: 82206-03-9
• Molecular Formula: C19H18 O8
• Molecular Weight: 0
• Mol File: 82206-03-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 654.8°C at 760 mmHg
• Flash Point: 237.7°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 4.86E-18mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: beta-D-Glucopyranuronic acid, 1-(1,1'-biphenyl)-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: beta-D-Glucopyranuronic acid, 1-(1,1'-biphenyl)-4-carboxylate(82206-03-9)
• EPA Substance Registry System: beta-D-Glucopyranuronic acid, 1-(1,1'-biphenyl)-4-carboxylate(82206-03-9)

Safety Data

• Hazardous Substances Data: 82206-03-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H18O8/c20-13-14(21)16(17(23)24)26-19(15(13)22)27-18(25)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13-16,19-22H,(H,23,24)/t13-,14-,15+,16-,19-/m0/s1

Upstream product

• 1105557-01-4 C₂₆H₂₆O₁₁ 
• 1105557-03-6 C₂₆H₂₆O₁₁ 
• 1289377-83-8 methyl 1-O-(p-phenyl)benzoyl-2,4-di-O-acetyl-β-D-glucopyranuronate 
• 716-76-7 3-phenylbenzoic acid 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 92-92-2 biphenyl-4-carboxylic acid 
• 947-84-2 2-Biphenylcarboxylic acid 

Relevant articles and documents

Characterization of chemo- and regioselectivity in enzyme-catalyzed consecutive hydrolytic deprotection of methyl acetyl derivatives of 1-β-O-acyl glucuronides

Methyl acetyl derivatives of 1-β-O-(o-, m-, or p-phenyl)benzoyl glucuronides 2a-c are fully deprotected by a one-pot consecutive enzyme-catalyzed hydrolytic reaction to afford 4a-c, without isolation of the O-deacetylated derivatives 3a-c. A lipase AS Amano from Aspergillus niger (LAS) and a carboxylesterase from Streptomyces rochei (CSR) showed high chemoselectivity toward the O-deacetylation of the o- and m-isomers, respectively. Chemoselective O-deacetylation of the p-isomer was promoted only in the presence of both enzymes. A lipase type B from Candida antarctica (CALB) was effective for the subsequent enzymatic hydrolysis of the methyl esters of 3a-c. LAS exhibited also regioselective 3-O-deacetylation activity to afford the corresponding 2,4-di-O-acetyl intermediates 5a-c, for which CSR showed higher O-deacetylation activity than that for 2a-c. In kinetic studies using p-nitrophenyl ester substrates, LAS exhibited a broader acyl preference, the octanoyl ester being most effectively hydrolysed, whereas CSR exhibited the highest hydrolytic activity toward the acetyl ester. LAS and CSR play complementary as well as synergistic roles in the O-deacetylation of 2 bearing R groups of different steric bulkiness.