title: Chemo-enzymatic synthesis of rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine and its analogues.
abstract: The synthesis of rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c), blood platelet activating ether lipid analogues has been achieved in a four-step sequence from epichlorohydrin (1). Etherification of epichlorohydrin with different alcohols namely tetradecyl (2a), hexadecyl (2b) and octadecyl (2c) alcohols gave glycidyl ethers (3a-c) with 78-80% yields. The second step involved opening of the epoxide by acetic anhydride to give acetylated products (4a-c, 76-78% yield), which were subsequently hydrolyzed selectively, a key step of the method employing a 1,3 specific lipase to obtain rac 1-O-alkyl-2- acetylglycerol (5a-c) with 45-50% yields. The hydrolyzed products (5a-c) were phosphorylated to obtain rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c) in 80-85% yields.
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology.
authors.forename: Tadla
authors.initials: T
authors.lastname: Vijeeta
authors.forename: Marrapu
authors.initials: M
authors.lastname: Balakrishna
authors.forename: Mallampalli Sri
authors.initials: MS
authors.lastname: Lakshmi Karuna
authors.forename: Bhamidipati Venkata
authors.initials: BV
authors.lastname: Surya Koppeswara Rao
authors.forename: Rachapudi Badari
authors.initials: RB
authors.lastname: Narayana Prasad
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry; D000107:Acetylation; D000438:Alcohols / Q000737:chemistry; D004811:Epichlorohydrin / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006868:Hydrolysis; D055601:Organic Chemistry Phenomena; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D000089:Acetic Anhydrides; D000438:Alcohols; D004852:Epoxy Compounds; C020344:glycidyl ethers; D004811:Epichlorohydrin; D010767:Phosphorylcholine; C031800:acetic anhydride