499-39-8

Basic information

• Product Name: O-α-D-galactopyranosyl-(1->6)-)-O-α-D-galactopyranosyl-(1->6)-O-D-glucopyranose
• Synonyms: O-α-D-galactopyranosyl-(1->6)-)-O-α-D-galactopyranosyl-(1->6)-O-D-glucopyranose
• CAS NO: 499-39-8
• Molecular Weight: 504.442
• Mol File: 499-39-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: O-α-D-galactopyranosyl-(1->6)-)-O-α-D-galactopyranosyl-(1->6)-O-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: O-α-D-galactopyranosyl-(1->6)-)-O-α-D-galactopyranosyl-(1->6)-O-D-glucopyranose(499-39-8)
• EPA Substance Registry System: O-α-D-galactopyranosyl-(1->6)-)-O-α-D-galactopyranosyl-(1->6)-O-D-glucopyranose(499-39-8)

Safety Data

• Hazardous Substances Data: 499-39-8(Hazardous Substances Data)

Upstream product

• 536-11-8 D-melibiose 
• 57-50-1 Sucrose 
• 470-55-3 stachyose 
• 7493-95-0 4-nitrophenyl α-D-galactoside 
• 83921-77-1 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Study of influential factors on oligosaccharide formation by fructosyltransferase activity during stachyose hydrolysis by pectinex ultra SP-L

The influence of reaction conditions for oligosaccharide synthesis from stachyose using a commercial enzymatic preparation from Aspergillus aculeatus (Pectinex Ultra SP-L) was studied. Oligosaccharides were analyzed by gas chromatography with flame ionization detection (GC-FID) and matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF-MS). Galactosyl-melibiose (DP3) was synthesized as a result of fructosidase activity, whereas fructosyl-stachyose (DP5) and difructosyl-stachyose (DP6) were formed as a consequence of the fructosyltransferase activity of Pectinex Ultra SP-L. The optimal reaction conditions for the synthesis of penta-and hexasaccharides were 60 °C, pH 5.5, 600 mg/mL stachyose, and 34 U/mL enzyme. Reaction time played an important role in oligosaccharide mixture composition constituted by 20% DP5, 0.7% DP6, 55% stachyose, 21% galactosyl-melibiose, and 1% monosaccharides after 1 h and 16% DP5, 4% DP6, 27% stachyose, 44% galactosyl-melibiose, and 2% monosaccharides after 3 h. In conclusion, stachyose could be used as a substrate for the enzymatic synthesis of new oligosaccharides that may open new opportunities in the development of future prebiotics.

Aspergillus nidulans α-galactosidase of glycoside hydrolase family 36 catalyses the formation of α-galacto-oligosaccharides by transglycosylation

The α-galactosidase from Aspergillus nidulans (AglC) belongs to a phylogenetic cluster containing eukaryotic α-galactosidases and -galacto-oligosaccharide synthases of glycoside hydrolase family 36 (GH36). The recombinant AglC, produced in high yield (0.65 g·L-1 culture) as His-tag fusion in Escherichia coli, catalysed efficient transglycosylation with α-(1→6) regioselectivity from 40 mm 4-nitrophenol -d-galactopyranoside, melibiose or raffinose, resulting in a 37-74% yield of 4-nitrophenol α-d-Galp-(1→6) α-d-Galp, α-d-Galp- (1→6) α- d-Galp-(1→6) α-d-Glcp and α-d-Galp- (1→6) α- d-Galp-(1→6) α-d-Glcp-(1→2) α-d-Fruf (stachyose), respectively. Furthermore, among 10 monosaccharide acceptor candidates (400 mm) and the donor 4-nitrophenol -d-galactopyranoside (40 mm), -(1→6) linked galactodisaccharides were also obtained with galactose, glucose and mannose in high yields of 39-58%. AglC did not transglycosylate monosaccharides without the 6-hydroxymethyl group, i.e. xylose, l-arabinose, l-fucose and l-rhamnose, or with axial 3-OH, i.e. gulose, allose, altrose and l-rhamnose. Structural modelling using Thermotoga maritima GH36 -galactosidase as the template and superimposition of melibiose from the complex with human GH27 α-galactosidase supported that recognition at subsite +1 in AglC presumably requires a hydrogen bond between 3-OH and Trp358 and a hydrophobic environment around the C-6 hydroxymethyl group. In addition, successful transglycosylation of eight of 10 disaccharides (400 mm), except xylobiose and arabinobiose, indicated broad specificity for interaction with the +2 subsite. AglC thus transferred -galactosyl to 6-OH of the terminal residue in the -linked melibiose, maltose, trehalose, sucrose and turanose in 6-46% yield and the -linked lactose, lactulose and cellobiose in 28-38% yield. The product structures were identified using NMR and ESI-MS and five of the 13 identified products were novel, i.e. α-d-Galp-(1→6) α-d-Manp; α-d-Galp-(1→6) α- d-Glcp-(1→4) α-d-Glcp; α-d-Galp-(1→6) α- d-Galp-(1→4) α-d-Fruf; α-d-Galp-(1→6) α-d-Glcp-(1→1) α-d-Glcp; and α-d-Galp-(1→6) α- d-Glcp-(1→3) α-d-Fruf.

Transgalactosylation catalyzed by alpha-galactosidase from Candida guilliermondii H-404

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