51411-23-5

Basic information

• Product Name: 1-O-alpha-D-glucopyranosyl-D-fructose
• Synonyms: 1-O-alpha-D-glucopyranosyl-D-fructose;trehalulose;1-O-α-D-Glucopyranosyl-D-fructose;D-Fructose, 1-O-a-D-glucopyranosyl-
• CAS NO: 51411-23-5
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.29648
• EINECS: 257-183-7
• Mol File: 51411-23-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 780.1 °C at 760 mmHg
• Flash Point: 290.8 °C
• Appearance: /
• Density: 1.69 g/cm³
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 11.85±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-O-alpha-D-glucopyranosyl-D-fructose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-alpha-D-glucopyranosyl-D-fructose(51411-23-5)
• EPA Substance Registry System: 1-O-alpha-D-glucopyranosyl-D-fructose(51411-23-5)

Safety Data

• Hazardous Substances Data: 51411-23-5(Hazardous Substances Data)

Usage

Uses

Trehalulose is a biologically active disaccharide with health benefits.

Synthetic route

D-Fructose (57-48-7) + Sucrose (57-50-1) → 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5)

Conditions	Yield
With α-glucosidase-substance from yeast

Sucrose (57-50-1) → D-Fructose (57-48-7) + D-glucose (50-99-7) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5)

Conditions	Yield
With trehalose synthase from Thermomonospora curvata DSM 43183 In aq. phosphate buffer at 30℃; for 0.5h; pH=6.5; Kinetics; Enzymatic reaction;

Sucrose (57-50-1) → 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0)

Conditions	Yield
With sucrose isomerase In aq. phosphate buffer at 30℃; for 0.333333h; pH=6; Kinetics; pH-value; Temperature; Enzymatic reaction;

D-2-deoxyglucose (154-17-6) + Sucrose (57-50-1) → 2-deoxy-maltose (58634-81-4, 58634-82-5, 132055-05-1, 132055-06-2) + C60H102O50 + C54H92O45 + C48H82O40 + C42H72O35 + C36H62O30 + D-turanose (547-25-1) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5)

Conditions	Yield
With recombinant amylosucrase from Neisseriapolysaccharea In aq. buffer at 35℃; Enzymatic reaction;

...Expand

1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) → α-D-glucopyranosyl-(1->6)-D-gulitol (20942-96-5) + 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8)

Conditions	Yield
With sodium tetrahydroborate In water at 37℃; for 4h; Reduction;

1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) → (2R)-1-O-α-D-glucosylglycerol (19432-18-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride / H2O / 4 h / 37 °C 2: lead tetraacetate; acetic acid / 20 °C 3: sodium borohydride / H2O / 4 h / 37 °C View Scheme

1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) → (S)-2-Hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propionaldehyde (266316-89-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / H2O / 4 h / 37 °C 2: lead tetraacetate; acetic acid / 20 °C View Scheme

1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) → (R)-2-Hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propionaldehyde (266316-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / H2O / 4 h / 37 °C 2: lead tetraacetate; acetic acid / 20 °C View Scheme

1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) → (2S)-1-O-α-O-D-glucosylglycerol

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride / H2O / 4 h / 37 °C 2: lead tetraacetate; acetic acid / 20 °C 3: sodium borohydride / H2O / 4 h / 37 °C View Scheme

D-Fructose (57-48-7) + D-Glucose (2280-44-6) + Sucrose (57-50-1) + isomaltose (499-40-1) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0) → α-D-glucopyranosyl-(1->6)-D-gulitol (20942-96-5) + 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8) + mannitol (69-65-8) + D-sorbitol (50-70-4) + isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; nickel In water at 20 - 130℃; under 22502.3 Torr; Product distribution / selectivity; Autoclave;

...Expand

D-Fructose (57-48-7) + D-Glucose (2280-44-6) + isomaltose (499-40-1) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0) → α-D-glucopyranosyl-(1->6)-D-gulitol (20942-96-5) + 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8) + mannitol (69-65-8) + D-sorbitol (50-70-4) + isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; nickel In water at 20 - 130℃; under 22502.3 - 97509.8 Torr; Product distribution / selectivity; Autoclave;

...Expand

Upstream product

• 57-48-7 D-Fructose 
• 57-50-1 Sucrose 
• 154-17-6 D-2-deoxyglucose 
• 7664-93-9 sulfuric acid 
• 512-65-2 α-D-galactopyranosyl-(1→6)-O-α-D-glucopyranosyl-(1→2)-[α-D-galactopyranosyl-(1→6)-O-β-D-fructofuranoside] 

Downstream Products

• 20942-96-5 α-D-glucopyranosyl-(1->6)-D-gulitol 
• 20942-99-8 1-O-α-D-glucopyranosyl-D-mannitol 
• 69-65-8 mannitol 
• 50-70-4 D-sorbitol 
• 534-73-6 isomaltitol 

Relevant articles and documents

Enzymatic synthesis of 2-deoxyglucose-containing maltooligosaccharides for tracing the location of glucose absorption from starch digestion

Abstract The ileal brake mechanism which induces a potentially beneficial slower gastric emptying rate and increased satiety is triggered by macronutrients including glucose from glycemic carbohydrates. For optimization of this diet-induced health benefit, there is the need for a way to determine the location of glucose deposition in the small intestine. Labeled 2-deoxyglucose (2-DG) can be used to trace the location of glucose absorption due to its accumulative property in the small intestine enterocytes. However, because pure glucose, or 2-DG, is directly absorbed in the proximal small intestine, we designed 2-DG containing maltooligosaccharides (2-DG-MOs) that can be used with a mild α-glucosidase inhibitor to attain an analytical method for determining location-specific delivery of glucose and its physiological effect.

Cloning, expression, properties, and functional amino acid residues of new trehalose synthase from Thermomonospora curvata DSM 43183

A new trehalose synthase (TreS) gene from Thermomonospora curvata DSM 43183 was cloned and expressed in Escherichia coli XL10-Gold. The purified recombinant enzyme (TreS-T.C) could catalyze the reversible interconversion of maltose and trehalose of sucrose into trehalulose without other disaccharides including isomaltulose at an optimum temperature of 35 °C and a pH of 6.5. The Km of TreS-T.C for maltose (96 mM) was lower than those for trehalose (198 mM) and sucrose (164 mM), suggesting that maltose is the optimum substrate. The maximum trehalose and trehalulose yields were 70% and >80%, respectively. Active TreS-T.C is a trimer comprising three identical 60 kDa subunits. Homology modeling analysis revealed that TreS-T.C had a GH13-typical (β/α)8 barrel catalytic domain. Two sites, one determining substrate specificity (L116) and the other affecting product formation (E330), were found near the active center by homology modeling combined with site-directed mutagenesis. TreS-T.C may be used effectively as a potential biocatalyst for the production of trehalose and trehalulose from maltose and sucrose in a one-step reaction, respectively. This study also provides a feasible and effective method for studying functional amino acid residues around TreS without performing crystal structure analysis and high-throughput screening.