- Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
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Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS3 approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.
- Mishra, Vivek K.,Buter, Jeffrey,Blevins, Molly S.,Witte, Martin D.,Van Rhijn, Ildiko,Moody, D. Branch,Brodbelt, Jennifer S.,Minnaard, Adriaan J.
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supporting information
p. 5126 - 5131
(2019/07/03)
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- Dansyl acetyl trehalose: A novel tool to investigate the cellular fate of trehalose
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A fluorescent derivative of trehalose with two dansyl groups (DAT) has been synthesized. It is characterised by a large Stokes shift, good permeability in human living cells and a well detectable fluorescent signal within the cells. Notably, in intestinal
- Locatelli, Alessandra,Iommarini, Luisa,Graziadio, Alessandra,Leoni, Alberto,Porcelli, Anna Maria,Iotti, Stefano,Malucelli, Emil,Francia, Francesco,Venturoli, Giovanni,Farruggia, Giovanna
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p. 15350 - 15356
(2019/05/27)
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- The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle
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We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a ke
- Jacobsen, Kristian M.,Keiding, Ulrik B.,Clement, Lise L.,Schaffert, Eva S.,Rambaruth, Neela D. S.,Johannsen, Mogens,Drickamer, Kurt,Poulsen, Thomas B.
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supporting information
p. 647 - 652
(2015/04/27)
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- Synthesis of macrocycles on the basis of diterpenoid isosteviol and trehalose
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Macrocyclic glycoterpenoids containing trehalose and isosteviol fragments have been synthesized. Selective screening has revealed compounds exhibiting antitubercular activity against H37RV, M. Avium and M. Terrae at a level comparable to the known antitub
- Garifullin,Sharipova,Strobykina,Andreeva,Kravchenko,Kataev
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p. 1488 - 1498
(2015/11/25)
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- Synthesis of the First Macrocyclic Glycoterpenoid Based on Trehalose and the Diterpenoid Isosteviol
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A macrocyclic glycoterpenoid containing the diterpenoid dihydroisosteviol (16-hydroxy-ent-beyeran-19- oic acid) and α,α′-trehalose linked by an ester spacer was synthesized.
- Garifullin,Sharipova,Strobykina, I. Yu.,Andreeva,Kataev
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p. 886 - 889
(2015/12/26)
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- Synthesis and structure - Activity relationships studies of brartemicin analogs as anti-invasive agents
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Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure-activity relationships, a series of 19 brartemicin analogs we
- Jiang, Yong-Li,Miyanaga, Satoshi,Han, Xiu-Zhen,Tang, Long-Qiang,Igarashi, Yasuhiro,Saiki, Ikuo,Liu, Zhao-Peng
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p. 531 - 537
(2013/10/21)
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- Self-assembling properties of 6-O-alkyltrehaloses under aqueous conditions
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In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reacti
- Kanemaru, Manami,Yamamoto, Kazuya,Kadokawa, Jun-Ichi
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experimental part
p. 32 - 40
(2012/09/21)
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- Self-assembling property of 6,6'-Di-O-octyltrehalose under aqueous conditions
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In this study, we synthesized a new trehalose-based amphiphile, 6,6'-di-O-octyltrehalose, from trehalose by five reaction steps. The SEM and TEM images of the sample prepared by drying its aqueous dispersion showed the formation of morphologically control
- Kanemaru, Manami,Yamamoto, Kazuya,Kadokawa, Jun-Ichi
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p. 954 - 956,3
(2020/08/31)
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- Synthesis and evaluation of trehalose-based compounds as anti-invasive agents
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Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to explore the preliminary structure-activity relationship and obtain more potent inhibitors, a series of brartemicin analogs
- Jiang, Yong-Li,Tang, Long-Qian,Miyanaga, Satoshi,Igarashi, Yasuhiro,Saiki, Ikuo,Liu, Zhao-Peng
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scheme or table
p. 1089 - 1091
(2011/04/16)
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- INOSITOL AND TREHALOSE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS FOR TREATING NEURODEGENERATIVE DISEASES COMPRISING THE SAME
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The invented inositol and trehalose derivatives, prepared by introducing multiple units of the guanidine group to the backbone molecules, show excellent blood-brain barrier permeability, and accordingly, it can be easily transported to the brain tissues and utilized for the treatment of neurodegenerative diseases such as Alzheimer's disease and Huntington's disease.
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Page/Page column 11-12
(2011/10/04)
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- INOSITOL AND TREHALOSE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS FOR TREATING NEURODEGENERATIVE DISEASES COMPRISING THE SAME
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The invented inositol and trehalose derivatives, prepared by introducing multiple units of the guanidine group to the backbone molecules, show excellent blood-brain barrier permeability, and accordingly, it can be easily transported to the brain tissues and utilized for the treatment of neurodegenerative diseases such as Alzheimer?s disease and Huntington's disease.
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Page/Page column 24
(2010/04/03)
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- Synthesis of per- and poly-substituted trehalose derivatives: Studies of properties relevant to their use as excipients for controlled drug release
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Per- and poly-substituted oligosaccharide derivatives, with trehalose cores, have been prepared and assessed for their potential for use as excipients in controlled-release formulations. The synthesized compounds, generally with acyl and amido substituent
- Baddeley, Thomas C.,Wardell, James L.
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experimental part
p. 198 - 221
(2010/03/03)
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- Ethambutol-sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis
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Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycoba
- Reynolds, Robert C.,Bansal, Namita,Rose, Jerry,Friedrich, Joyce,Suling, William J.,Maddry, Joseph A.
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p. 164 - 179
(2007/10/03)
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- Glycophanes, cyclodextrin-cyclophane hybrid receptors for apolar binding in aqueous solutions. A stereoselective carbohydrate-carbohydrate interaction in water
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The synthesis and complexing properties of a new type of neutral chiral receptors, glycophanes 4-6 and 9-14, are reported. They may be considered as cyclodextrin-cyclophane hybrids because carbohydrate molecules, lipophilic cavities, and aromatic interact
- Coterón, Jose M.,Vicent, Cristina,Bosso, Claude,Penadés, Soledad
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p. 10066 - 10076
(2007/10/02)
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- A Novel Class of Neutral Chiral Cyclophanes from α,α'-Trehalose
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The synthesis and preliminary complexation studies of a new class of chiral cyclophanes 1-6, with properties comparable to cyclodextrins and cyclophanes, is described.
- Penades, S.,Coteron, J. M.
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p. 683 - 684
(2007/10/02)
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- Glycosylated trehalose. Synthesis of the oligosaccharides of the glycolipid-type antigens from Mycobacterium smegmatis.
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The oligosaccharide components, 3-O-Me-beta-D-Glcp-(1----3)-beta-D-Glcp-(1----4)-beta-D-Glcp-(1----6)- alpha-D-Glcp-(1----1)-alpha-D-Glcp (1) and beta-D-Glcp-(1----4)-beta-D-Glcp-(1----6)-alpha-D-Glcp-(1----1)-alpha-D- Glcp, of the glycolipid-type antigen
- Szurmai,Kerekgyarto,Harangi,Liptak
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p. 313 - 325
(2007/10/02)
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- STRUCTURAL COMPARISON OF TREHALOSE ANOMERS; THE X-RAY CRYSTAL STRUCTURES OF αα-(2,3,4,-TRI-O-METHYL-6-METHANESULPHONYL)GLUCOPYRANOSYL-1-O-(2',3',4'-TRI-O-METHYL-6'-METHANESULPHONYL)GLUCOPYRANOSE, AND ITS ββ-ISOMER.
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The structures of the title compounds have been determined by X-ray analysis.The αα-isomer was refined to a final R-factor of 0.073, and the ββ-isomer was refined to a final R-factor of 0.072.The anomeric geometry is compared with previously determined va
- Brown, John M.,Cook, Stephen J.,Jones, Richard H.,Khan, Riaz
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p. 5089 - 5096
(2007/10/02)
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