26277-05-4Relevant academic research and scientific papers
Total Synthesis of Phospholipomannan of Candida albicans
Ali, Asif,Gannedi, Veeranjaneyulu,Singh, Parvinder Pal,Vishwakarma, Ram A.
, p. 7757 - 7771 (2020/07/25)
First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.
Intramolecular α-glucosaminidation: Synthesis of mycothiol
Ajayi, Kehinde,Thakur, Vinay V.,Lapo, Robert C.,Knapp, Spencer
supporting information; experimental part, p. 2630 - 2633 (2010/08/22)
A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively α-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.
A synthesis of dioctanoyl phosphatidylinositol
Elliott, Thomas S.,Nemeth, Joseph,Swain, Simon A.,Conway, Stuart J.
experimental part, p. 2809 - 2813 (2010/03/30)
A synthesis of the naturally occurring enantiomer of phosphatidylinositol is reported. A resolution strategy, using camphor as a chiral auxiliary is employed to obtain the desired, enantiomerically pure, inositol derivative. Dioctanoyl lipid chains are appended to the molecule, which are shorter than the naturally occurring lipid chains, providing the molecule with enhanced water solubility.
Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis
Boonyarattanakalin, Siwarutt,Liu, Xinyu,Michieletti, Mario,Lepenies, Bernd,Seeberger, Peter H.
scheme or table, p. 16791 - 16799 (2009/04/14)
The emergence of multidrug-resistant tuberculosis (TB) and problems with the BCG tuberculosis vaccine to protect humans against TB have prompted investigations into alternative approaches to combat this disease by exploring novel bacterial drug targets and vaccines. Phosphatidylinositol mannosides (PIMs) are biologically important glycoconjugates and represent common essential precursors of more complex mycobacterial cell wall glycolipids including lipomannan (LM), lipoarabinomannan (LAM), and mannan capped lipoarabinomannan (ManLAM). Synthetic PIMs constitute important biochemical tools to elucidate the biosynthesis of this class of molecules, to reveal PIM interactions with host cells, and to investigate the function of PIMs as potential antigens and/or adjuvants for vaccine development. Here, we report the efficient synthesis of all PIMs including phosphatidylinositol (Pl) and phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6). Robust synthetic protocols were developed for utilizing bicyclic and tricyclic orthoesters as well as mannosyl phosphates as glycosylating agents. Each synthetic PIM was equipped with a thiol-linker for immobilization on surfaces and carrier proteins for biological and immunological studies. The synthetic PIMs were immobilized on microarray slides to elucidate differences in binding to the dendritic cell specific intercellular adhesion molecule-grabbing nonintegrin (DC-SIGN) receptor. Synthetic PIMs served as immune stimulators during immunization experiments in C57BL/6 mice when coupled to the model antigen keyholelimpet hemocyanin (KLH).
New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the endoplasmic reticulum membrane does not depend on the stereochemistry of the lipid
Vishwakarma, Ram A.,Vehring, Stefanie,Mehta, Anuradha,Sinha, Archana,Pomorski, Thomas,Hermann, Andreas,Menon, Anant K.
, p. 1275 - 1283 (2007/10/03)
Glycerophospholipid flip-flop across biogenic membranes such as the endoplasmic reticulum (ER) is a fundamental feature of membrane biogenesis. Flip-flop requires the activity of specific membrane proteins called flippases. These proteins have yet to be i
Phospholipid derivatives having a polyhydroxylated aliphatic carbocycle
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Page/Page column 6, (2008/06/13)
The present invention relates to a phospholipid derivative having a substituted or unsubstituted polyhydroxylated aliphatic carbocycle attached to the sn-1 or sn-2 position of the glycerol backbone, a pharmaceutical composition comprising said phospholipid, a method for preparing said phospholipid and a medicament comprising said phospholipid.
Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis
Andresen, Thomas L.,Skytte, Dorthe M.,Madsen, Robert
, p. 2951 - 2957 (2007/10/03)
A divergent strategy is described for synthesis of the novel phosphatidylinositols 1-3. The synthetic approach commences from benzyl-protected methyl 6-iodo-6-deoxy-α-D-glucopyranoside, which undergoes zinc-mediated reductive fragmentation followed by vin
Synthesis of 2-deoxy-2-C-alkylglucosides of myo-inositol as possible inhibitors of a N-deacetylase enzyme in the biosynthesis of mycothiol
Gammon, David W.,Hunter, Roger,Steenkamp, Daniel J.,Mudzunga, Theophilus T.
, p. 2045 - 2049 (2007/10/03)
Two new analogues of 1-D-1-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-myo-inositol, a biosynthetic intermediate in the production of mycothiol in the Mycobacteria have been synthesized. Both the 2-deoxy-2-C-(2′-hydroxypropyl)-D-glucoside 5, and the 2-deox
Practical unequivocal synthesis of phosphatidyl-myo-inositols
Aneja, Rajindra,Aneja, Sarla G.
, p. 847 - 850 (2007/10/03)
The direct phosphatidylation of 1D-2,3,4,5,6-penta-O-benzyl-myo-inositol with sn-3-phosphatidic acid and subsequent hydrogenolytic debenzylation produces 1D-1-(sn-3-phosphatidyl)-myo-inositol in excellent yield (>90%) and unequivocal structural and stereo
Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol
Koto,Hirooka,Yoshida,Takenaka,Nagamitsu,Sakurai,Zen,Yago,Tomonaga
, p. 2521 - 2529 (2007/10/03)
Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.
