25018-27-3Relevant articles and documents
Trehalose-based neuroprotective autophagy inducers
Arosio, Daniela,Assoni, Giulia,Colombo, Eleonora,Frapporti, Giulia,Gornati, Davide,Perez-Carrion, Maria Dolores,Piccoli, Giovanni,Polito, Laura,Seneci, Pierfausto
supporting information, (2021/03/23)
A small set of trehalose-centered putative autophagy inducers was rationally designed and synthesized, with the aim to identify more potent and bioavailable autophagy inducers than free trehalose, and to acquire information about their molecular mechanism
Glycosyl Fluorides as Intermediates in BF3·OEt2-Promoted Glycosylation with Trichloroacetimidates
Nielsen, Michael M.,Stougaard, Bolette A.,Bols, Mikael,Glibstrup, Emil,Pedersen, Christian M.
supporting information, p. 1281 - 1284 (2017/03/17)
Glycosyl fluorides have been found to be important intermediates in glycosylations with trichloroacetimidate donors and BF3·OEt2 activation (0.2–1 equiv.). Low-temperature NMR spectroscopy experiments revealed that the α-trichloroacetimidate was transformed into the glycosyl fluoride with inversion of stereochemistry, whereas the β anomer was not. A concerted mechanism was suggested for the stereospecific formation of glycosyl fluorides, which is not accounted for in the classic mechanism.
I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation
Xiong, Xingquan,Yi, Chao,Han, Qian,Shi, Lin,Li, Sizhong
, p. 237 - 243 (2015/09/28)
A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG400-based ionic liquid catalyst (I2/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I2/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.
CELL-PERMEABLE VARIANTS OF TREHALOSE AND METHODS FOR THE PROTECTION OF LIVING CELLS
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Page/Page column 0027, (2014/01/08)
A method for synthesizing variants of Tre; novel Tre variants; and a method for introducing Tre in sufficient concentration into the intracellular environment suitable to store treated mammalian cells, treat an aggregation disease, and protect treated cells from oxygen radicals are disclosed.
Regioselective silyl/acetate exchange of disaccharides yields advanced glycosyl donor and acceptor precursors
Hsieh, Hsiao-Wu,Schombs, Matthew W.,Witschi, Mark A.,Gervay-Hague, Jacquelyn
supporting information, p. 9677 - 9688 (2013/10/22)
Glycoconjugates are composed of carbohydrate building blocks linked together in a multitude of ways giving rise to diverse biological functions. Carbohydrates are especially difficult to synthetically manipulate because of the similar reactivity of their numerous and largely equivalent hydroxyl groups. Hence, methodologies for both the efficient protection and selective modification of carbohydrate alcohols are considered important synthetic tools in organic chemistry. When per-O-TMS protected mono- or disaccharides in a mixture of pyridine and acetic anhydride are treated with acetic acid, regioselective exchange of silicon for acetate protecting groups occurs. Acid concentration, thermal conditions, and microwave assistance mediate the silyl/acetate exchange reaction. Regiocontrol is achieved by limiting the equivalents of acetic acid, and microwave irradiation hastens the process. We coined the term Regioselective Silyl Exchange Technology (ReSET) to describe this process, which essentially sets the protecting groups anew. To demonstrate the scope of the reaction, the conditions were applied to lactose, melibiose, cellobiose, and trehalose. ReSET provided rapid access to a wide range of orthogonally protected disaccharides that would otherwise require multiple synthetic steps to acquire. The resulting bifunctional molecules are poised to serve as modular building blocks for more complex glycoconjugates.
DETECTION OF MYCOBACTERIA
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Page/Page column 87-89, (2011/04/18)
A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.
Flow chemistry kinetic studies reveal reaction conditions for ready access to unsymmetrical trehalose analogues
Patel, Mitul K.,Davis, Benjamin G.
supporting information; experimental part, p. 4232 - 4235 (2010/11/18)
Monofunctionalization of trehalose, a widely-found symmetric plant disaccharide, was studied in a microreactor to give valuable kinetic insights that have allowed improvements in desymmetrization yields and the development of a reaction sequence for large scale monofunctionalizations that allow access to probes of trehalose's biological function.
Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis
Deng, Shenglou,Gangadharmath, Umesh,Chang, Cheng-Wei Tom
, p. 5179 - 5185 (2007/10/03)
Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation (acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.
H-Beta zeolite as an efficient catalyst for per-O-acetylation of mono- and disaccharides
Bhaskar, Pallooru Muni,Loganathan, Duraikkannu
, p. 129 - 131 (2007/10/03)
Among the six different zeolites examined, H-beta is demonstrated to be a highly efficient and selective catalyst for the per-O-acetylation of various mono-and disaccharides and methyl glycosides.
Synthesis and semisynthesis of some structural elements of oligo-mannose type N-glycoproteins
Szurmai, Zoltan,Janossy, Lorant,Szilagyi, Zoltan,Vekey, Karoly
, p. 417 - 437 (2007/10/03)
For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-α-D-mannopyranosyl-(1→2)-α-D-mannopyranose octaacetate (19) and O-α-D-mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→2)- α-D-mannopyranose undecaacetate (20) were ob
