29781-76-8

Usage

Chemical structure

A glycerol backbone with two palmitoyl fatty acid chains attached at the 1 and 2 positions and a glucose molecule attached at the 3 position.

Classification

A glycolipid, which is a type of lipid that contains a carbohydrate (glycosyl) group.

Occurrence

Found in the membranes of certain microorganisms and plant cells.

Function in cells

Important for maintaining the structural integrity and stability of the cell membrane.

Involvement in cellular processes

Participates in various signaling and recognition processes.

Industrial applications

Potential use in the pharmaceutical and cosmetic industries due to its unique structure and properties.

Anti-inflammatory properties

Research suggests that 1,2-di-O-palmitoyl-3-O-(glucopyranosyl)glycerol may have anti-inflammatory properties.

Antioxidant properties

The compound may also possess antioxidant properties, which could be beneficial in various applications.

Drug delivery systems

Its unique structure may allow for potential use in drug delivery systems, enhancing the effectiveness of certain medications.

Research focus

Further investigation into the properties and potential applications of 1,2-di-O-palmitoyl-3-O-(glucopyranosyl)glycerol is needed to fully understand its capabilities and maximize its potential in various industries.

InChI:InChI=1/C41H78O10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(43)48-32-34(33-49-41-40(47)39(46)38(45)35(31-42)51-41)50-37(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35,38-42,45-47H,3-33H2,1-2H3/t34?,35-,38-,39+,40-,41?/m1/s1

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Relevant academic research and scientific papers

An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens

Mycoplasma fermentans possesses unique α-glycolipid antigens (GGPL-I and GGPL-III) at the cytoplasm membrane, which carry a phosphocholine group at the sugar primary (6-OH) position. This paper describes a practical synthetic pathway to a GGPL-I homologue (C16:0) and its diastereomer, in which our one-pot α-glycosylation method was effectively applied. The synthetic GGPL-I isomers were characterized with 1H NMR spectroscopy to determine the equilibrium among the three conformers (gg, gt, tg) at the acyclic glycerol moiety. The natural GGPL-I isomer was found to prefer gt (54%) and gg (39%) conformers around the lipid tail, while adopting all of the three conformers with equal probability around the sugar position. This property was very close to what we have observed with respect to the conformation of phosphatidylcholine (DPPC), suggesting that the Mycoplasma glycolipids GGPLs may constitute the cytoplasm fluid membrane together with ubiquitous phospholipids, without inducing stereochemical stress.

Synthesis of biologically active galactosyl and glucosyl-glycerol derivatives

Galactosyl and glucosyl-glycerol derivatives which mimic the structure of the lipoteichoic acid of Staphylococcus aureus were synthesized by using a chiral glycerol derivative. Glucosyl-glycerol derivatives (14 and 22) had stronger anti-inflammatory activ

Synthesis of phosphatidyl-α-glucosyl glycerol containing a dioleoyl phosphatidyl moiety. Application of the tetraisopropyldisiloxane-1,3-diyl (tips) protecting group in sugar chemistry. part III1 1 For part I and II see references 11 and 39, respectively.

In this study we demonstrate that the tetraisopropyldisiloxane-1,3-diyl protecting group could be introduced, in a two step procedure, at the 3'- and 4'-hydroxyl functions of α-glucosyldiglyceride 3 to give derivative 6. Compound 6 could be selectively condensed with a suitably protected phosphatidyl part 9 at its primary hydroxyl function to afford the protected glycophospholipid 10a. The phosphatidyl part 9 was obtained by phosphorylation of optically pure 1,2-di-O-oleoyl-sn-glycerol (8a) with phosphoditriazolide 7b. Finally, the 2,4-dichlorophenyl and TIPS protecting groups were removed from 10a by syn-4-nitro-benzaldoximate and fluoride ions, respectively, to afford glycophospholipid 10c.