Synthesis of 1-O-(1,2-Di-O-palmitoyl-SN-glycero-3-phosphoryl)-2-O-α-D-mannopyranosyl-D-MYO-inositol: a fragment of mycobacterial phospholipids

Elie, C. J. J.; Dreef, C. E.; Verduyn, R.; Marel, Gijs A. van der; Boom, J. H. Van

doi:10.1016/s0040-4020(01)81026-7

Cited by 43 publications

(18 citation statements)

References 30 publications

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“…Finally, the utility of the α‐mannosynthase was tested in highly crowded substrates: the target synthesis of α‐mannosylated inositols. Mannosylated myo ‐inositols are components of the cell wall glycolipids found in Mycobacterium tuberoculosis and, as such, have been the targets of traditional glycoside syntheses 42. 43 Reaction of more hindered acceptor myo ‐inositol ( 5 ) was more sluggish than those for some of the other acceptors.…”

Section: Methodsmentioning

confidence: 99%

Creation of an α‐Mannosynthase from a Broad Glycosidase Scaffold

Yamamoto¹,

Davis²

2012

Angewandte Chemie

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α‐Mannoside synthetisierende Biokatalysatoren wurden durch Mutation einer α‐Glucosidase der GH31‐Familie erhalten. Diese zeigt Plastizität gegenüber Veränderungen an der 2‐OH‐Position von Donorsubstraten. Ein Fluorid‐Donorreagens ergab mithilfe dieser α‐Mannosynthase, die eine niedrige (unerwünschte) Oligomerisierungsaktivität aufweist, mehrere mono‐α‐mannosylierte Konjugate.

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Section: Methodsmentioning

confidence: 99%

Creation of an α‐Mannosynthase from a Broad Glycosidase Scaffold

Yamamoto¹,

Davis²

2012

Angewandte Chemie

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“…The general strategy for the synthesis of PIM analogues follows synthetic sequences similar to those developed by other groups for the preparation of PIM1 and PIM2 structures, [25][26][27][28][29][30][31] namely the preparation of a (di)mannosylated scaffold and of a glycerolipid carrying two fatty acid residues, followed by the connection of these entities by a phosphodiester linkage in the last stage of the synthesis. In our synthesis, a notable improvement is the use of a methoxyacetylated mannopyranosyl donor in the glycosylation step: such esters provide efficient stereocontrol of the glycosylation, while their selective cleav-age without affecting the glycerolipid esters is facilitated at the end of the synthesis by the higher reactivity of the methoxyacetyl groups [32] compared to normal acetyl groups.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

Phosphatidyl myo‐Inositol Mannosides Mimics Built on an Acyclic or Heterocyclic Core: Synthesis and Anti‐inflammatory Properties

et al. 2011

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Phosphatidyl myo-inositol mannosides (PIMs) are constituents of the mycobacterial cell wall and possess immunomodulatory activities. Certain PIM derivatives have immunoprotective activity and are of interest as anti-inflammatory agents. In order to identify simplified analogues of PIMs that retain this interesting activity, we have prepared a series of new analogues based either on an acyclic or on a heterocyclic scaffold that replaces the inositol moiety, and evaluated these compounds for their inhibition of LPS-induced release of NO and pro-inflammatory cytokines by macrophages. It was found that the inositol moiety can be favourably replaced by an aza-cyclitol (trihydroxy-piperidine) or an oxa-cyclitol (trihydroxy-tetrahydropyran) unit, and that the configuration of the OH-carrying carbons does not play a significant role. The biological activity is reduced if the nitrogen atom is free in the aza-cyclitol unit.

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“…Removal of the TBS group with TBAF gave 12 in 87 % yield. Although treatment of 12 with benzylamine to remove the benzyl (Bn) group [23,24] resulted in the formation of decomposed products, treatment with NaI in the presence of acetic acid (AcOH) afforded 13 in moderate yield (65 %), with concomitant formation of decomposition products. Finally, removal of the Boc group of 13 with TFA afforded conjugate 1 in 87 % yield.…”

Section: Synthesis Of Conjugates 1 Andmentioning

confidence: 99%

Design and Synthesis of Sphingomyelin–Cholesterol Conjugates and Their Formation of Ordered Membranes

Matsumori

Tanada

Nozu

et al. 2011

Chemistry A European J

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A lipid raft is a cholesterol (Chol)-rich microdomain floating in a sea of lipid bilayers. Although Chol is thought to interact preferentially with sphingolipids such as sphingomyelin (SM), rather than with glycerophospholipids, the origin of the specific interaction has remained unresolved, primarily because of the high mobility of lipid molecules and weak intermolecular interactions. In this study, we synthesized SM-Chol conjugates with functionally designed linker portions to restrain Chol mobility and examined their formation of ordered membranes by a detergent insolubility assay, fluorescence anisotropy experiments, and fluorescence-quenching assay. In all of the tests, membranes prepared from the conjugates showed properties of ordered domains comparable to a SM-Chol (1:1) membrane. To gain insight into the structure of bilayers composed from the conjugates, we performed molecular dynamics simulations with 64 molecules of the conjugates, which suggested that the conjugates form a stable bilayer structure by bending at the linker portion and, mostly, reproduce the hydrogen bonds between the SM and Chol portions. These results imply that the molecular recognition between SM and Chol in an ordered domain is essentially reproduced by the conjugated molecules and, thus, demonstrates that these conjugate molecules could potentially serve as molecular probes for understanding molecular recognition in lipid rafts.

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Synthesis of 1-O-(1,2-Di-O-palmitoyl-SN-glycero-3-phosphoryl)-2-O-α-D-mannopyranosyl-D-MYO-inositol: a fragment of mycobacterial phospholipids

Cited by 43 publications

References 30 publications

Creation of an α‐Mannosynthase from a Broad Glycosidase Scaffold

Creation of an α‐Mannosynthase from a Broad Glycosidase Scaffold

Phosphatidyl myo‐Inositol Mannosides Mimics Built on an Acyclic or Heterocyclic Core: Synthesis and Anti‐inflammatory Properties

Design and Synthesis of Sphingomyelin–Cholesterol Conjugates and Their Formation of Ordered Membranes

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