TY - JOUR
T1 - Preparation and characterization of well defined d-erythro sphingomyelins
AU - Cohen, R.
AU - Barenholz, Y.
AU - Gatt, S.
AU - Dagan, A.
PY - 1984/10
Y1 - 1984/10
N2 - A simple semisynthetic procedure for the preparation of various d-erythro sphingomyelins (SPMs), differing in their acyl chains, is described. They were prepared by one-step condensation of the desired free fatty acid with sphingosyl phosphorylcholine (SPC) using dicyclohexylcarbodiimide. The d-erythro SPMs were obtained in high purity, high yields and resemble bovine brain SPM in their chromatographic behavior, infrared, circular dichroism (CD) and proton NMR (PMR) spectra as well as in their rate of hydrolysis by Staphylococcus aureus sphingomyelinase. Multilamellar vesicles can be prepared from the semisynthetic SPMs. Their thermotropic behavior is dependent mainly on the acyl chain though it is also affected by the heterogeneity of the sphingosine base composition. Intact sealed small unilamellar vesicles (SUV) cannot be prepared from a single semisynthetic saturated SPM but can be prepared from their mixtures. This acylation procedure can also be applied for preparing simple neutral glycosphingolipids. The sphingolipids prepared by this method can be used to study metabolism, enzymology and physicochemical properties of d-erythro well defined simple sphingolipids.
AB - A simple semisynthetic procedure for the preparation of various d-erythro sphingomyelins (SPMs), differing in their acyl chains, is described. They were prepared by one-step condensation of the desired free fatty acid with sphingosyl phosphorylcholine (SPC) using dicyclohexylcarbodiimide. The d-erythro SPMs were obtained in high purity, high yields and resemble bovine brain SPM in their chromatographic behavior, infrared, circular dichroism (CD) and proton NMR (PMR) spectra as well as in their rate of hydrolysis by Staphylococcus aureus sphingomyelinase. Multilamellar vesicles can be prepared from the semisynthetic SPMs. Their thermotropic behavior is dependent mainly on the acyl chain though it is also affected by the heterogeneity of the sphingosine base composition. Intact sealed small unilamellar vesicles (SUV) cannot be prepared from a single semisynthetic saturated SPM but can be prepared from their mixtures. This acylation procedure can also be applied for preparing simple neutral glycosphingolipids. The sphingolipids prepared by this method can be used to study metabolism, enzymology and physicochemical properties of d-erythro well defined simple sphingolipids.
KW - liposomes
KW - membranes
KW - sphingomyelins (physical properties)
KW - stereospecific sphingolipids
KW - stereospecific sphingolipids (partial synthesis)
KW - stereospecific sphingomyelins
UR - http://www.scopus.com/inward/record.url?scp=0021717570&partnerID=8YFLogxK
U2 - 10.1016/0009-3084(84)90079-3
DO - 10.1016/0009-3084(84)90079-3
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C2 - 6499099
AN - SCOPUS:0021717570
SN - 0009-3084
VL - 35
SP - 371
EP - 384
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
IS - 4
ER -