Configurational analysis of long-chain alkanediols.
Long-chain 1,2-alkanediols can be separated into their enantiomers by thin-layer chromatography of the bis-L-acetylmandelates. The method is also applicable to the separation of enantiomeric 1,3-alkanediols. Both 2-hydroxy fatty acids and 1,2-alkanediols derived from diester waxes of rat skin have the D-configuration. The D-enantiomer of 2DL-1,2-octadecanediol is preferentially utilized by myelinating rat brain in the formation of choline phospholipids having a 1,2-octadecanediol backbone. The D-configuration of the chiral center at carbon-2 of 2-acyl-1,2-alkanediol phosphocholine corresponds to the configuration at carbon-2 of 1,2-diacyl-sn-glycero-3-phosphocholine.
D000818:Animals; D001921:Brain / Q000378:metabolism; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000032:analysis; D005233:Fatty Alcohols / Q000032:analysis; D006880:Hydroxy Acids / Q000032:analysis; D008968:Molecular Conformation; D009186:Myelin Sheath / Q000378:metabolism; D010713:Phosphatidylcholines / Q000096:biosynthesis; D051381:Rats; D012867:Skin / Q000032:analysis; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D005227:Fatty Acids; D005233:Fatty Alcohols; D006880:Hydroxy Acids; D010713:Phosphatidylcholines