- Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases
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A glycophosphatidylinositol tetrasaccharide fragment was synthesized to mimic the core features of primary model, that of Saccharomyces cerevisiae. The salient feature of this approach is centered on the quick access to various α-1,2- and α-1,6-mannosyl a
- Belz, Tyson F.,Williams, Spencer J.
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p. 2053 - 2058
(2021/08/31)
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- The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application
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The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac
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Paragraph 0041; 0046; 0047
(2017/04/28)
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- 3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application
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The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl
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Paragraph 0035; 0038; 0113
(2017/08/25)
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- Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
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Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.
- Wang, Ying-Hsin,Yeh, Hsien-Wei,Wang, Hsiao-Wen,Yu, Chia-Chun,Guh, Jih-Hwa,Liu, Der-Zen,Liang, Pi-Hui
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p. 118 - 135
(2013/07/27)
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- Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters
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Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
- Uriel, Clara,Ventura, Juan,Gomez, Ana M.,Lopez, J. Cristobal,Fraser-Reid, Bert
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experimental part
p. 795 - 800
(2012/03/22)
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- Mitochondrial affinity of guanidine-rich molecular transporters built on monosaccharide scaffolds: Stereochemistry and lipophilicity
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We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.
- Lee, Woo Sirl,Kim, Wanil,Kim, Kyong-Tai,Chung, Sung-Kee
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experimental part
p. 2286 - 2300
(2012/06/16)
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- Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues
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α-Bisabolol β-d-fucopyranoside, a cytotoxic naturally occurring compound, was efficiently synthesized along with five other α-bisabolol glycosides (β-d-glucoside, β-d-galactoside, α-d-mannoside, β-d-xyloside and α-l-rhamnoside). Glycosidation of α-bisabol
- Piochon, Marianne,Legault, Jean,Gauthier, Charles,Pichette, Andre
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experimental part
p. 228 - 236
(2009/09/05)
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- Practical synthesis of sugar monophosphonucleotides
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A reliable procedure for the preparation of sugar nucleoside monophosphates is presented, which involves condensation of an activated glycosyl-1-H- phosphonate with an appropriately protected nucleoside and simple end-product isolation via lithium perchlo
- Wlassoff, Wjatschesslaw A.,Finlay, Richard M. J.,Hamilton, Chris J.
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p. 2927 - 2934
(2008/02/13)
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- Oligomannoside mimetics by glycosylation of 'octopus glycosides' and their investigation as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli
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The glycocalyx of eukaryotic cells is composed of glycoconjugates, which carry highly complex oligosaccharide portions. To elucidate the biological role and function of the glycocalyx in cell-cell communication and cellular adhesion processes, glycomimeti
- Dubber, Michael,Sperling, Oliver,Lindhorst, Thisbe K.
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p. 3901 - 3912
(2008/09/18)
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- Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol
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A nonavalent glycodendrimer bearing terminal α-D-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having
- Al-Mughaid, Hussein,Grindley, T. Bruce
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p. 1390 - 1398
(2007/10/03)
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- Sugar/Steroid/Sugar Conjugates: Sensitivity of Lipid Binding to Sugar Structure
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(Equation presented) Three steroids, each bearing a sugar on rings A and D, have been synthesized. Their effect on the "melting" behavior of a lipid bilayer depends on whether the sugar is glucose, galactose, or mannose. Packing constraints dictate how th
- Mbadughat, Bessie N. A.,Menger, Fredric M.
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p. 4041 - 4044
(2007/10/03)
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- Synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranosides revisited
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Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding α-1-acetates. When β-1-acetates were more readily available, these were converted to the α-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl α-D-mannopyranosides were obtained in excellent yields.
- Saksena, Rina,Zhang, Jian,Kovac, Pavol
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p. 453 - 470
(2007/10/03)
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- Synthesis of Carbohydrate-Centered Oligosaccharide Mimetics Equipped with a Functionalized Tether
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Synthetic glycoclusters have gained substantial attention as mimetics of multivalent glycoconjugates. For their proposed glycobiological applications, it is advantageous to incorporate a functionalized tether into the clusters, which allows coupling to so
- Dubber, Michael,Lindhorst, Thisbe K.
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p. 5275 - 5281
(2007/10/03)
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- A synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranoside
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The first high yield synthesis is reported of 2-(trimethylsilyl)ethyl α-D-mannopyranoside using 2-O-benzoylated mannosyl donors, as precursors.
- Pozsgay, Vince
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p. 7175 - 7178
(2007/10/02)
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