Stereocontrolled Synthesis of <i>Lyso</i>‐phosphatidyl β‐D‐Glucoside

Kano, Koki; Ishii, Nozomi; Hirabayashi, Yoshio; Kamiguchi, Hiroyuki; Greimel, Peter; Matsuo, Ichiro

doi:10.1002/slct.202102176

Cited by 6 publications

(3 citation statements)

References 20 publications

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“…H-phosphonates are a class of phosphonylated intermediates that have been used in the syntheses of other glycerophospholipids, including phosphatidyl inositols [ 34 , 35 , 36 , 37 ], phosphatidyl ethanolamine [ 38 ], phosphatidyl choline [ 38 ], and phosphatidyl serine [ 20 , 38 ]. They have also been used in the total synthesis of glycophospholipids [ 39 , 40 , 41 ], as well as in nucleoside-based phospholipids [ 24 ] and drugs [ 42 ]. To our surprise, they have not, however, been utilized in the synthesis of PG.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology

et al. 2022

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Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis route utilized phosphoramidite methodology that addressed issues surrounding fatty acid substrate scope and glycerol backbone modifications prior to headgroup phosphorylation, but faltered in the reproducibility of the overall pathway due to purification challenges. Herein, we present a robust pathway to optically pure PG in fewer steps, utilizing H-phosphonates that features a chromatographically friendly and stable triethyl ammonium H-phosphonate salt. Our route is also amendable to the simultaneous installation of different acyl chains, either saturated or unsaturated, on the glycerol backbone.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology

et al. 2022

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“…LysoPtdGlc was synthesized according to previous reports 20 , 47 , 48 and briefly described in Supplementary Materials and Methods. OxLDL from human plasma was from Thermo Fisher Scientific (Waltham, Germany).…”

Section: Methodsmentioning

confidence: 99%

Lysophosphatidylglucoside/GPR55 signaling promotes foam cell formation in human M2c macrophages

Shimai,

Hanafusa,

Nakayama

et al. 2023

Sci Rep

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Atherosclerosis is a major cause of cerebral and cardiovascular diseases. Intravascular plaques, a well-known pathological finding of atherosclerosis, have a necrotic core composed of macrophages and dead cells. Intraplaque macrophages, which are classified into various subtypes, play key roles in maintenance of normal cellular microenvironment. Excessive uptake of oxidized low-density lipoprotein causes conversion of macrophages to foam cells, and consequent progression/exacerbation of atherosclerosis. G-protein-coupled receptor 55 (GPR55) signaling has been reported to associate with atherosclerosis progression. We demonstrated recently that lysophosphatidylglucoside (lysoPtdGlc) is a specific ligand of GPR55, although in general physiological ligands of GPR55 are poorly understood. Phosphatidylglucoside is expressed on human monocytes and can be converted to lysoPtdGlc. In the present study, we examined possible involvement of lysoPtdGlc/GPR55 signaling in foam cell formation. In monocyte-derived M2c macrophages, lysoPtdGlc/GPR55 signaling inhibited translocation of ATP binding cassette subfamily A member 1 to plasma membrane, and cholesterol efflux. Such inhibitory effect was reversed by GPR55 antagonist ML193. LysoPtdGlc/GPR55 signaling in M2c macrophages was involved in excessive lipid accumulation, thereby promoting foam cell formation. Our findings suggest that lysoPtdGlc/GPR55 signaling is a potential therapeutic target for inhibition of atherosclerosis progression.

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“…In addition, several analogs have been chemically synthesized; the glucose moiety of PtdGlc has been converted into other monosaccharide components, or the phosphate group has been converted into thiophosphate ( Greimel et al, 2008 ). The synthesis of LysoPtdGlc ( 2 ) ( Kano et al, 2021 ) and its analog, in which the phosphate moiety is converted into a squaryl diamide group, has also been reported ( Ding et al, 2018 ). The biological activities of PtdGlc ( 1 ) and LysoPtdGlc ( 2 ) have been investigated using these analogs.…”

Section: Phosphatidylglucoside (Ptdglc)mentioning

confidence: 99%

Structures, functions, and syntheses of glycero-glycophospholipids

Osawa,

Fujikawa,

Shimamoto

2024

Front. Chem.

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Biological membranes consist of integral and peripheral protein-associated lipid bilayers. Although constituent lipids vary among cells, membrane lipids are mainly classified as phospholipids, glycolipids, and sterols. Phospholipids are further divided into glycerophospholipids and sphingophospholipids, whereas glycolipids are further classified as glyceroglycolipids and sphingoglycolipids. Both glycerophospholipids and glyceroglycolipids contain diacylglycerol as the common backbone, but their head groups differ. Most glycerolipids have polar head groups containing phosphate esters or sugar moieties. However, trace components termed glycero-glycophospholipids, each possessing both a phosphate ester and a sugar moiety, exist in membranes. Recently, the unique biological activities of glycero-glycophospholipids have attracted considerable attention. In this review, we describe the structure, distribution, function, biosynthesis, and chemical synthetic approaches of representative glycero-glycophospholipids—phosphatidylglucoside (PtdGlc) and enterobacterial common antigen (ECA). In addition, we introduce our recent studies on the rare glycero-glyco“pyrophospho”lipid, membrane protein integrase (MPIase), which is involved in protein translocation across biomembranes.

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Stereocontrolled Synthesis of Lyso‐phosphatidyl β‐D‐Glucoside

Cited by 6 publications

References 20 publications

Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology

Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology

Lysophosphatidylglucoside/GPR55 signaling promotes foam cell formation in human M2c macrophages

Structures, functions, and syntheses of glycero-glycophospholipids

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