title: Concise synthesis of ether analogues of lysobisphosphatidic acid.
abstract: We describe a versatile, efficient method for the preparation of ether analogues of (S,S)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (S,S)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA. [reaction: see text]
authors.affiliation: Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.
authors.forename: Guowei
authors.initials: G
authors.lastname: Jiang
authors.forename: Yong
authors.initials: Y
authors.lastname: Xu
authors.forename: Thomas
authors.initials: T
authors.lastname: Falguières
authors.forename: Jean
authors.initials: J
authors.lastname: Gruenberg
authors.forename: Glenn D
authors.initials: GD
authors.lastname: Prestwich
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry*; D004797:Enzyme-Linked Immunosorbent Assay; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008246:Lysophospholipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D050178:Monoglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation; D013237:Stereoisomerism
chemical_list: D000911:Antibodies, Monoclonal; D004987:Ethers; D008246:Lysophospholipids; D050178:Monoglycerides; C012786:bis(monoacylglyceryl)phosphate