1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose - CAS 604-68-2
Category:
Carbohydrates
Product Name:
1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose
Synonyms:
a-D-Glucose pentaacetate
CAS Number:
604-68-2
Molecular Weight:
390.34
Molecular Formula:
C16H22O11
COA:
Inquire
MSDS:
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Structure:
Monosaccharides
Chemical Structure
CAS 604-68-2 1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose

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Reference Reading


1.Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents.
Khodair AI1. Nucleosides Nucleotides Nucleic Acids. 2001 Sep;20(9):1735-50.
A series of 3-alkyl-5-((Z))-arylidene-2-thiohydantoins 4a-1 were synthesized from the direct condensation of the aromatic aldehydes with 3-alkyl-2-thiohydantoins 3a-c, which in turn were prepared from the reaction of glycine (1) and alkyl isothiocyanates 2a-c. The alkylation of 4a-1 with methylthioethyl chloride gave 5-((Z))-arylidene-3-alkyl-S-(2-methylthioethyl)-2-thiohydantoins 5a-e. S-Glucosylation took place on the reaction of 4a-1 with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide under anhydrous alkaline conditions. These structures have been confirmed from a model study of the coupling of 4a with methylthioethyl chloride and alpha-D-glucose pentaacetate, respectively under Lewis acid conditions.
2.Differences in the time course of the metabolic response of B and non-B pancreatic islet cells to D-glucose and metabolized or non-metabolized hexose esters.
Mercan D1, Kadiata MM, Malaisse WJ. Biochem Biophys Res Commun. 1999 Aug 27;262(2):346-9.
The early (min </= 1) and late (min 45) changes in NAD(P)H fluorescence caused by alpha-D-glucose pentaacetate, beta-L-glucose pentaacetate, and beta-D-galactose pentaacetate (1.7 mM each), alone or together with either L-leucine (10.0 mM) or D-glucose (8.3 mM), were monitored in purified pancreatic B and non-B rat islet cells. Whilst D-glucose caused a rapid increase in the NAD(P)H signal in B-cells, but not so in non-B cells, alpha-D-glucose pentaacetate, but not the two other monosaccharide esters, rapidly augmented the NAD(P)H signal in both B and non-B cells. After 45 min, the NAD(P)H signal was increased by either D-glucose in both B and non-B islet cells or alpha-D-glucose pentaacetate. At this late time, beta-L-glucose pentaacetate also increased the NAD(P)H signal in B cells exposed to L-leucine. These findings emphasize the relevance of differences in the time course of D-glucose uptake by B and non-B islet cells as a determinant of rapid changes in redox state.
3.Metabolism of D-[1,2-13C]glucose and alpha-D-[1,2-13C]glucose pentaacetate in tumoral pancreatic islet cells.
Ladriere L1, Kadiata MM, Verbruggen I, Willem R, Malaisse WJ. Int J Mol Med. 2000 Apr;5(4):331-3.
Tumoral pancreatic islet cells of the RINm5F line were incubated, in groups of 25x106 cells each, for 120 min at 37 degrees C in media (5. 0 ml) containing either alpha-D-[1,2-13C]glucose pentaacetate (1.7 mM) or both D-[1,2-13C]glucose (1.7 mM) and acetate (8.5 mM). In both cases, the amounts of 13C-enriched metabolites (D-glucose, L-lactate and acetate) and non-enriched metabolites (acetate) recovered in the incubation medium after incubation were close to the initial amount of esterified or non-esterified D-[1, 2-13C]glucose and acetate, respectively. The 13C-enriched metabolites corresponded mainly to double-labelled D-[1, 2-13C]glucose, L-[2,3-13C]lactate and [1,2-13C]acetate. The output of L-[2,3-13C]lactate and [1,2-13C]acetate was about 3-4 times lower in the cells exposed to alpha-D-[1,2-13C]glucose pentaacetate than in those incubated with unesterified D-[1,2-13C]glucose. These findings indicate that, despite extensive hydrolysis of alpha-D-[1, 2-13C]glucose pentaacetate in the RINm5F cells, the hexose moiety of the ester is less efficiently metabolized than unesterified D-[1, 2-13C]glucose tested at the same molar concentration (1.