- Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors
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The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.
- Norberg, Oscar,Wu, Bin,Thota, Niranjan,Ge, Jian-Tao,Fauquet, Germain,Saur, Ann-Kathrin,Aastrup, Teodor,Dong, Hai,Yan, Mingdi,Ramstr?m, Olof
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- Mannose-binding geometry of pradimicin A
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Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t
- Nakagawa, Yu,Doi, Takashi,Taketani, Takara,Takegoshi,Igarashi, Yasuhiro,Ito, Yukishige
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supporting information
p. 10516 - 10525
(2013/08/23)
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- Direct C-H amination of arenes with alkyl azides under rhodium catalysis
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New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright
- Shin, Kwangmin,Baek, Yunjung,Chang, Sukbok
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supporting information
p. 8031 - 8036
(2013/08/23)
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- Synthesis of novel sugar-lactam conjugates using the Aube reaction
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An efficient and convenient method for the synthesis of sugar-lactam conjugates is reported starting from readily available sugar azides using the Aube reaction. Cyclic azido alcohols are used in the Aube reaction for the first time in a carbohydrate setting. The resulting glycoconjugates could be further used to increase the chemical diversity on the sugar backbone, and may find potential applications as glycomimetics, peptidomimetics, in glycotargeting and in CNS drug delivery.
- Kurhade, Suresh E.,Mengawade, Tanaji,Bhuniya, Debnath,Palle, Venkata P.,Reddy, D. Srinivasa
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supporting information; experimental part
p. 744 - 747
(2011/04/16)
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- Synthesis of analogs of 1,1-linked galactosyl mannoside as mimetics of sialyl Lewis X tetrasaccharide
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Methods have been developed for the incorporation of hydrophobic groups with and without positive or negative charge to position-6 of the mannose residue in the 1,1-linked disaccharide as mimetics of sialyl Lewis X tetrasaccharide in order to enhance binding affinity to selectins.
- Hiruma, Kazumi,Kanie, Osamu,Wong, Chi-Huey
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p. 15781 - 15792
(2007/10/03)
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- SYNTHESIS OF (1->1)-BONDED RHAMNOPYRANOSYL-RHAMNOPYRANOSIDES CONTAINING L,L AND L,D BUILDING-STONES. HIGH-FIELD 1H- AND 13C-NMR SPECTROSCOPIC STUDIES ON THE CONFORMATION OF THE INTERGLYCOSIDIC BONDS
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Rhamnosylation of 2,3,4-tri-O-acetyl-L- (1) and 2,3,4-tri-O-benzyl-D-rhamnopyranose (9) with α-acetobromo-L-rhamnose resulted in fully protected α-L, α-L-, α-L, β-L-, α-D,α-L-, and β-D,α-L-rhamnopyranosyl-rhamnopyranosides.The signal of the anomeric carbo
- Liptak, A.,Goendoer, A.
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p. 309 - 322
(2007/10/02)
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