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Literature DB >> 10891176

Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry.

J Chevallier¹, N Sakai, F Robert, T Kobayashi, J Gruenberg, S Matile.

Abstract

An expeditious route to synthetic lysobisphosphatidic acid S,S-1, its enantiomer, and regioisomers is reported. Synthetic difficulties concerning lipid stability and stereochemistry are bypassed using a phosphite triester approach in combination with multiple silyl protection. Spectroscopic studies evidence that acyl group migration in S,S-1 is accelerated by nonpolar solvents and inhibited by pyridine.

Entities: Chemical

Mesh：

Substances：
Lysophospholipids

Year: 2000 PMID： 10891176 DOI： 10.1021/ol0059246

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

11 in total

1. Concise synthesis of ether analogues of lysobisphosphatidic acid.

Authors: Guowei Jiang; Yong Xu; Thomas Falguières; Jean Gruenberg; Glenn D Prestwich
Journal: Org Lett Date: 2005-09-01 Impact factor: 6.005

2. Effect of late endosomal DOBMP lipid and traditional model lipids of electrophysiology on the anthrax toxin channel activity.

Authors: Nnanya Kalu; Yoav Atsmon-Raz; Sanaz Momben Abolfath; Laura Lucas; Clare Kenney; Stephen H Leppla; D Peter Tieleman; Ekaterina M Nestorovich
Journal: Biochim Biophys Acta Biomembr Date: 2018-08-23 Impact factor: 3.747

3. pH-dependent formation of membranous cytoplasmic body-like structure of ganglioside G(M1)/bis(monoacylglycero)phosphate mixed membranes.

Authors: Tomohiro Hayakawa; Asami Makino; Motohide Murate; Ichiro Sugimoto; Yasuhiro Hashimoto; Hiroshi Takahashi; Kazuki Ito; Tetsuro Fujisawa; Hirotami Matsuo; Toshihide Kobayashi
Journal: Biophys J Date: 2006-10-20 Impact factor: 4.033

Review 4. Biological function of the cellular lipid BMP-BMP as a key activator for cholesterol sorting and membrane digestion.

Authors: Hichem D Gallala; Konrad Sandhoff
Journal: Neurochem Res Date: 2010-12-07 Impact factor: 3.996

5. 2,2'-Bis(monoacylglycero) PO4 (BMP), but Not 3,1'-BMP, increases membrane curvature stress to enhance α-tocopherol transfer protein binding to membranes.

Authors: Matilda Baptist; Candace Panagabko; Jonathan D Nickels; John Katsaras; Jeffrey Atkinson
Journal: Lipids Date: 2015-01-21 Impact factor: 1.880

Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry.

1. Concise synthesis of ether analogues of lysobisphosphatidic acid.

2. Effect of late endosomal DOBMP lipid and traditional model lipids of electrophysiology on the anthrax toxin channel activity.

3. pH-dependent formation of membranous cytoplasmic body-like structure of ganglioside G(M1)/bis(monoacylglycero)phosphate mixed membranes.

Review 4. Biological function of the cellular lipid BMP-BMP as a key activator for cholesterol sorting and membrane digestion.

5. 2,2'-Bis(monoacylglycero) PO4 (BMP), but Not 3,1'-BMP, increases membrane curvature stress to enhance α-tocopherol transfer protein binding to membranes.

6. Cyclodextrin triggers MCOLN1-dependent endo-lysosome secretion in Niemann-Pick type C cells.

Review 7. Lipid sorting and multivesicular endosome biogenesis.

8. Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor.

Review 9. Life in the lumen: The multivesicular endosome.

10. Intracellular cholesterol trafficking is dependent upon NPC2 interaction with lysobisphosphatidic acid.