Lipids inositol chemistry

Chemistry of Inositol Lipid Mediated Cellular Signalling. Potter, B. V. L. Lampe. D. Angew. Chem, Int. Ed. Engl. 1995, 34, 1933-1972. 

The current review is of necessity selective. Over the two year period covered, there has been impressive advances in several areas of P(V) chemistry. For example, biological aspects of quinquevalent phosphorus acids chemistry continue to increase in importance. A wide variety of natural and unnatural phosphates including inositols, lipids, some carbohydrates and their phospho-nates, phosphinates and fluorinated analogues has been synthesized. Special attention has been paid to the synthesis of phosphorus analogues of all types of amino acids and some peptides. Numerous investigations of phosphate ester hydrolysis and related reactions continue to be reported. Interest in approaches to easier detoxification of insecticides continues. A number of new and improved stereoselective synthetic procedures have been elaborated. The importance of enantioselective and dynamic kinetic asymmetric transformations is illustrated in many publications. 

As concerns the chemistry of these glycolipids, they contain either an eater linkage between the sugar moiety and the lipid moiety, as in cord factor and in wax D of Mycobacteria, or they are glycosides of phenolic alcohols (as in mycoside B) or of inositol (as in the phosphoglycolipids), or they can be linked to the carboxyl group of D-alanine (as in mycoside C). 

Nakade, S., Rhee, S.K., Hamanaka, H., and Mikoshiba, K. (1994) Cyclic AMP-dependent phosphorylation of an immunoaffinity-purified homotetrameric inositol 1,4,5-trisphosphate receptor (type I) increases Ca flux in reconstituted lipid vesicles. Journal of Biological Chemistry, 269 6735-6742. 

O-position of the GPI glycan core. The complex structure of GPIs is a fantastic challenge for synthetic chemists (96), as GPI synthesis requires the integration of methods developed in different areas in organic chemistry, including carbohydrate, inositol, lipid, and phosphate chemistry. 

Loewus, F. (1965) Inositol Metabolism and Cell Wall Formation in Plants , Federation Proceedings of the Federation of American Societies for Experimental Biology, 24, 855-62 Lotan, R. (1980) Effects of Vitamin A and its Analogs (Retinoids) on Normal and Neoplastic Cells , Biochimica et Biophysica Acta, 605, 33-91 Lowden, J.A O Brien, J.S. (1979) Sialidosis a Review of Human Neurominidase Deficiency , American Journal of Human Genetics, 31, 1-18 Lucas, J.J., Waechter, C.J. Lennarz, W.J. (1975) The Participation of Lipid-linked Oligosaccharide in Synthesis of Membrane Glycoproteins , Journal of Biological Chemistry, 250,1992-2002... 

The chemistry of ROS has been studied by several laboratories, and recently reviewed by Daemen (1973). Over 90% of the protein is rhodopsin, a photosensitive glycoprotein of molecular weight around 35,000, which is imbedded in a lipid bilayer. Phospholipids make up about 96% of the lipids of cattle ROS and cholesterol is the major component of the neutral lipid fraction. Phosphatidyl choline (PC) and phosphatidyl ethanolamine (PE) are the major phospholipids in all species examined, with phosphatidyl serine (PS), phosphatidyl inositol (PI), and sphingomyelin (SPh) present in lesser amounts (Anderson and Maude, 1972). Detailed analysis of the photoreceptor membranes of vertebrate species ranging from frogs to humans have revealed a fairly constant phospholipid class and protein composition (Basinger and Anderson, unpublished). 

Mvo-inositol 1,4-diphosphate (38), the racemate of a metabolite of second messenger myo-inositol 1,4,5-triphosphate and its diphosphorothioate analogue (39) have been synthesised from f 1 -1 2.4 S-di-O-isopropylidene-mvo-inositol by way of phosphite intermediates. Similarly, (-mvo-inositol 1,3,4-triphosphate has been obtained from f W2.4.S-tri-O-benzyl-myo-inositol Phosphite chemistry was also employed in the preparation of diphosphorylated and diphosphonylated Lipid A monosaccharide analogues (40). Related Lipid A components are mentioned in Chapter 9. Methyl 3-deoxv-a-D-manno-oct-2-ulopyranosidonic acid 4-phosphate has been synthesised and its chemical stability studied. ... 

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