129214-38-6Relevant articles and documents
Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives
Kern, Mallory K.,Pohl, Nicola L. B.
, (2020/06/08)
Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation
Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection
Rintelmann, Chelsea L.,Grinnage-Pulley, Tara,Ross, Kathleen,Kabotso, Daniel E.K.,Toepp, Angela,Cowell, Anne,Petersen, Christine,Narasimhan, Balaji,Pohl, Nicola
, p. 623 - 632 (2019/04/17)
Leishmaniasis, a neglected tropical disease, currently infects approximately 12 million people worldwide with 1 to 2 million new cases each year in predominately underdeveloped countries. The treatment of the disease is severely underdeveloped due to the
Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale
Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun
, p. 4720 - 4727 (2018/07/06)
A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.
Exploring glycosylation reactions under continuous-flow conditions
Cancogni, Damiano,Lay, Luigi
, p. 2873 - 2878 (2015/01/16)
The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.
Synthesis of tri- and tetra-mannosides based on sequential one-pot three-component glycosylation reactions
Basu, Nabamita,Mukherjee, Mana Mohan,Chaudhury, Aritra,Ghosh, Rina
, p. 1815 - 1820 (2014/01/17)
Expeditious syntheses of tri- and tetra-mannosides were carried out based on sequential one-pot glycosylation strategy. In both of these syntheses TMSOTf activated trichloroacetimidate, the first glycosyl donor, and inexpensive readily accessible trichlor
Expedient and versatile formation of novel amino-deoxy-ketoheptuloses
Leshch, Yevgeniy,Jacobsen, Anna,Thimm, Julian,Thiem, Joachim
supporting information, p. 4948 - 4951 (2013/10/22)
Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-keto
Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation
Tiwari, Vinod K.,Kumar, Amit,Schmidt, Richard R.
, p. 2945 - 2956 (2012/07/27)
In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra
Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor
Richichi, Barbara,Luzzatto, Lucio,Notaro, Rosario,Marca, Giancarlo La,Nativi, Cristina
scheme or table, p. 88 - 93 (2011/05/12)
The biological role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure-function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources
1-methyl 1′-cyclopropylmethyl (MCPM) as an anomeric protecting group
Yu, Siu Hong,Whitfield, Dennis M.
experimental part, p. 5750 - 5761 (2011/08/22)
A pragmatic approach for preparing glycoconjugates of complex oligosaccharides is to prepare the oligosaccharide as a building block with most of its protecting groups exchanged to protecting groups whose cleavage and other manipulations are highly compatible with the functional groups of complex aglycones. For such an approach the reducing end sugar of the building bloc must be protected with a cleavable protecting group during the oligosaccharide synthesis. We demonstrate that the acid labile 1-methyl 1′- cyclopropylmethyl (MCPM) can be effectively used for this purpose. A trisaccharide glycolipid and a disaccharide glycoamino acid are prepared. The absolute chirality of the MCPM in one key acceptor is determined by a combination of NMR NOE measurements, DFT molecular modeling and Noyori catalyst catalyzed asymmetric reduction.
The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?
Mueller, Lisa N.,Muhle-Goll, Claudia,Biskup, Moritz B.
supporting information; scheme or table, p. 3294 - 3299 (2010/08/21)
The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.
