58511-73-2

Basic information

• Product Name: glucogallin
• Synonyms: glucogallin;1-O-(3,4,5-Trihydroxybenzoyl)-β-D-glucopyranose;1-O-Galloyl β-D-glucopyranose;3,4,5-Trihydroxybenzoic acid β-D-glucopyranosyl ester;Gallic acid β-D-glucopyranosyl ester;β-D-Glucopyranose 1-(3,4,5-trihydroxybenzoate);1-o-Galloylglucose;beta-Glucogallin
• CAS NO: 58511-73-2
• Molecular Formula: C13H16O10
• Molecular Weight: 332.26014
• Mol File: 58511-73-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 681.1°Cat760mmHg
• Flash Point: 681.1°Cat760mmHg
• Appearance: /
• Density: 1.76g/cm³
• Vapor Pressure: 1.74E-19mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: glucogallin(CAS DataBase Reference)
• NIST Chemistry Reference: glucogallin(58511-73-2)
• EPA Substance Registry System: glucogallin(58511-73-2)

Safety Data

• Hazardous Substances Data: 58511-73-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H16O10/c1-21-12-9(18)8(17)10(19)13(23-12)22-11(20)4-2-5(14)7(16)6(15)3-4/h2-3,8-10,12-19H,1H3/t8-,9-,10+,12-,13?/m0/s1

Upstream product

• 2485-62-3 L-Cysteine methyl ester 
• 148077-26-3 furosin 
• 106822-42-8 Heptabenzyl-α-D-glucogallin 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 492-62-6 alpha-D-glucopyranose 
• 133-89-1 UDP-glucose 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 1555352-04-9 1-O-(3,4,5-tris(benzyloxy)benzoyl)-4,6-O-benzylidene-β-D-glucopyranose 
• 1195367-79-3 2,3,4,6-tetra-O-benzyl-1-(3’,4’,5’-tri-O-benzylgalloyl)-β-D-glucopyranose 
• 79814-54-3 1-galloyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 99877-83-5 4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose 
• 52238-31-0 2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose 
• 99877-82-4 hexagalloyl β-D-glucose 
• 99877-85-7 C₅₅H₄₀O₃₄ 

Relevant articles and documents

Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses

An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-d-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism was indicated for nonstereoselective glycosylation in DMF. The SN2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One-or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected α-d-glucose.

NOVEL GLYCOSYLTRANSFERASE, NOVEL GLYCOSYLTRANSFERASE GENE, AND NOVEL GLYCOSYL DONOR COMPOUND

An object of the present invention is to provide a sugar donating reagent comprising a sugar donor compound other than a sugar nucleotide and an enzyme capable of catalyzing a glycosyl transfer reaction using a sugar donor compound other than a sugar nucleotide. The present invention provides the following: a sugar donating reagent containing a compound of formula (A): wherein R 1 is independently selected from hydrogen, or C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl in which each of the groups is unsubstituted or substituted with one or more groups selected from OH, F, Cl, Br, I, CN, NO 2 , and SO 2 , n is 0, 1, 2, 3, 4 or 5, m is 0 or 1, and X represents a monosaccharide bound via a 2 bond on its anomeric carbon; a glycosyltransferase capable of catalyzing a glycosyl transfer reaction using the sugar donor; and a glycosyltransferase gene comprising DNA encoding the glycosyltransferase.

Identification of UGT84A13 as a candidate enzyme for the first committed step of gallotannin biosynthesis in pedunculate oak (Quercus robur)

A cDNA encoding the ester-forming hydroxybenzoic acid glucosyltransferase UGT84A13 was isolated from a cDNA library of Quercus robur swelling buds and young leaves. The enzyme displayed high sequence identity to resveratrol/hydroxycinnamate and hydroxybenzoate/hydroxycinnamate glucosyltransferases from Vitis species and clustered to the phylogenetic group L of plant glucosyltransferases, mainly involved in the formation of 1-O-β-d-glucose esters. In silico transcriptome analysis confirmed expression of UGT84A13 in Quercus tissues which were previously shown to exhibit UDP-glucose:gallic acid glucosyltransferase activity. UGT84A13 was functionally expressed in Escherichia coli as N-terminal His-tagged protein. In vitro kinetic measurements with the purified recombinant enzyme revealed a clear preference for hydroxybenzoic acids as glucosyl acceptor in comparison to hydroxycinnamic acids. Of the preferred in vitro substrates, protocatechuic, vanillic and gallic acid, only the latter and its corresponding 1-O-?-D-glucose ester were found to be accumulated in young oak leaves. This indicates that in planta UGT84A13 catalyzes the formation of, 1-O-galloyl-?-D-glucose, the first committed step of gallotannin biosynthesis.