Synthesis and purity assessment of tetra-and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid

A Zamyatina, H Sekljic, H Brade, P Kosma

Index: Zamyatina, Alla; Sekljic, Harald; Brade, Helmut; Kosma, Paul Tetrahedron, 2004 , vol. 60, # 52 p. 12113 - 12137

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Citation Number: 15

Abstract

Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1, 4′-bisphosphoryl as well as the related 4′-monophosphoryl derivatives of lipid A were synthesized.(R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3′ and N-acylated with (R)-3- ...