Concise synthesis of ether analogues of lysobisphosphatidic acid.
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]
Jiang
Guowei
G
Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.
Xu
Yong
Y
Falguières
Thomas
T
Gruenberg
Jean
J
Prestwich
Glenn D
GD
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
D000911:Antibodies, Monoclonal; D004987:Ethers; D008246:Lysophospholipids; D050178:Monoglycerides; C012786:bis(monoacylglyceryl)phosphate