28140-37-6Relevant academic research and scientific papers
Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH
Adinolfi, Matteo,Iadonisi, Alfonso,Ravidà, Alessandra,Schiattarella, Marialuisa
, p. 7863 - 7866 (2003)
Peracetylated sugars can be efficiently converted into the corresponding 1,2-ethylidenes, -orthoesters, and -glycals via the in situ generation of glycosyl iodides promoted by I2/Et3SiH. The approach is straightforward and avoids isolation of the sensitive iodinated intermediates.
Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates
Fadlan, Arif,Tanimoto, Hiroki,Ito, Tatsuya,Aritomi, Yusuke,Ueno, Maho,Tokuda, Masaya,Hirohara, Shiho,Obata, Makoto,Morimoto, Tsumoru,Kakiuchi, Kiyomi
, p. 1848 - 1858 (2018/03/06)
The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.
Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins
Wawryszyn, Mirella,Sauter, Paul F.,Nieger, Martin,Koos, Martin R. M.,Koehler, Christine,Luy, Burkhard,Lemke, Edward A.,Br?se, Stefan
, p. 4296 - 4305 (2018/08/29)
Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.
A convenient and efficient synthetic approach to mono-, di-, and tri-O-mannosylated Fmoc amino acids
Chen, Liqun,Tan, Zhongping
, p. 2190 - 2193 (2013/04/24)
A convenient and highly efficient synthesis of mono-, di-, and tri-O-mannosylated Fmoc-Ser and Thr is described. The short synthetic route and high overall yield highlight the synthetic utility of this unified approach.
Novel approaches for the synthesis and activation of thio- and selenoglycoside donors
Valerio, Silvia,Iadonisi, Alfonso,Adinolfi, Matteo,Ravida, Alessandra
, p. 6097 - 6106 (2008/02/09)
(Chemical Equation Presented) Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.
Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors
Lam, Son N.,Gervay-Hague, Jacquelyn
, p. 2387 - 2390 (2007/10/03)
(Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodid
Synthesis of tetrasaccharide building block of the O-specific polysaccharide of Shigella dysenteriae type 1
Pozsgay,Glaudemans,Robbins,Schneerson
, p. 10249 - 10264 (2007/10/02)
A glycosyl trichloroacetimidate derivative (1) of the tetrasaccharide α-D-Galp-(1→3)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap was synthesized in a highly stereoselective, stepwise manner, using methyl 1-thioglycosides of L-rhamnose, 2-azido-2-deoxy-D-glucose and D-galactose, as major intermediates. The protecting group scenario in compound 1 permits regioselective deblocking at its 'non-reducing end' unit. Therefore 1 is a suitable intermediate for the preparation of extended fragments of the title polysaccharide.
HALOENAMINES - II. A RAPID AND EFFICIENT SYNTHESIS OF CARBOHYDRATE 1,2-ORTHOESTERS
Ernst, Beat,Mesmaeker, Alain De,Wagner, Beatrice,Winkler, Tammo
, p. 6167 - 6170 (2007/10/02)
Carbohydrate exo 1,2-orthoesters are obtained in good to excellent yields by treating furanose and pyranose hemiacetals first with 1.1 eq. 1-chloro-2,N,N-trimethyl-propenylamine and then with the appropriate alcohols in the presence of NEt3.
Synthesis of the Carbohydrate Moiety of Bleomycin. 2,3,4,6-Tetra-O-substituted D-Mannose Derivatives
Millar, Alan,Kim, Ki Hyup,Minster, David K.,Ohgi, Tadaaki,Hecht, Sidney M.
, p. 189 - 196 (2007/10/02)
As part of the synthesis of the carbohydrate moiety of bleomycin , two different approaches were employed for the synthesis of appropriate 3-O-carbamoylmannose precursors.One approach, which required
