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1 article(s) from Zamyatina, Alla

Aminosugar-based immunomodulator lipid A: synthetic approaches

Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

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Graphical Abstract

Figure 1: (A) Gram-negative bacterial membrane with LPS as major component of the outer membrane; (B) structu...

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Figure 2: Structures of representative TLR4 ligands: TLR4 agonists (E. coli lipid A, N. meningitidis lipid A ...

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Figure 3: (A) Co-crystal structure of the homodimeric E. coli Ra-LPS·hMD-2∙TLR4 complex (PDB code: 3FXI); (B)...

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Figure 4: Co-crystal structures of (A) hybrid TLR4·hMD-2 with the bound antagonist eritoran (PDB: 2Z65, TLR4 ...

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Scheme 1: Synthesis of E. coli and S. typhimurium lipid A and analogues with shorter acyl chains.

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Scheme 2: Synthesis of N. meningitidis Kdo-lipid A.

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Scheme 3: Synthesis of fluorescently labeled E. coli lipid A.

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Scheme 4: Synthesis of H. pylori lipid A and Kdo-lipid A.

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Scheme 5: Synthesis of tetraacylated lipid A corresponding to P. gingivalis LPS.

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Scheme 6: Synthesis of pentaacylated P. gingivalis lipid A.

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Scheme 7: Synthesis of monophosphoryl lipid A (MPLA) and analogues.

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Scheme 8: Synthesis of tetraacylated Rhizobium lipid A containing aminogluconate moiety.

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Scheme 9: Synthesis of pentaacylated Rhizobium lipid A and its analogue containing ether chain.

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Scheme 10: Synthesis of pentaacylated Rhizobium lipid A containing 27-hydroxyoctacosanoate lipid chain.

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Scheme 11: Synthesis of zwitterionic 1,1′-glycosyl phosphodiester: a partial structure of GalN-modified Franci...

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Scheme 12: Synthesis of a binary 1,1′-glycosyl phosphodiester: a partial structure of β-L-Ara4N-modified Burkh...

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Scheme 13: Synthesis of Burkholderia lipid A containing binary glycosyl phosphodiester linked β-L-Ara4N.

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Review

Published 04 Jan 2018

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