73960-72-2Relevant academic research and scientific papers
Functionalization of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid Methyl Ester
Okamoto, Kaoru,Kondo, Tadao,Goto, Toshio
, p. 631 - 636 (1987)
The acetyl protected 2-deoxy-2,3-dehydroneuraminic acid methyl ester was functionalized by modifying its 2,3-double bond to convert it into new glycosyl donors such as 2,3-dibromo-, 2,3-epoxy-, and 2-halo-3-hydroxyneuraminic acid derivatives.
Selective synthesis of Neu5Ac2en and its oxazoline derivative using BF3·Et2O
Morais, Goreti Ribeiro,Oliveira, Rudi Santiago,Falconer, Robert A.
, p. 1642 - 1644 (2009)
Application of the Lewis acid BF3·Et2O to the selective synthesis of 5-acetamido-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto-non-2-enonic acid (Neu5Ac2en) and the related oxazoline, methyl 7,8,9-tri-O-acetyl-2,3,4,5-tetradeoxy-2,3-didehydro-2,3-trideoxy-4′,5′-dihydro-2′-methyloxazolo[5,4-d]- d-glycero-d-talo-non-2-enonate is described.
A facile synthesis of N-acetylneuraminic acid glycal
Kulikova, Nadezhda Yu.,Shpirt, Anna M.,Kononov, Leonid O.
, p. 4113 - 4114 (2006)
Treatment of the readily available peracetylated N-acetylneuraminic acid glycosyl chloride [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5- trideoxy-β-D-glycero-D-galactononulopyranosonate)] with anhydrous Na 2HPO4 in refluxing MeCN quantitatively affords the peracetylated N-acetylneuraminic acid glycal [methyl 5-acetamido-4,7,8,9-tetra- O-acetyl-3,5-dideoxy-2,6-anhydro-D-glycero-D-galacto-non-2-enonate], which can be isolated from the reaction mixture by simple filtration and subsequent evaporation of the solvent. No glycal formation was detected at room temperature even after prolonged treatment with Na2HPO4. The method proposed is experimentally simple and allows ready preparation of substantial amounts of the title compound, which is an important intermediate in sialic acid chemistry. Georg Thieme Verlag Stuttgart.
A facile synthesis of 2-deoxy-2,3-didehydroneuraminic acid derivatives
Ikeda, Kiyoshi,Konishi, Koji,Sano, Kimihiko,Tanaka, Kiyoshi
, p. 163 - 165 (2000)
The 2-thio- or 2-selenoglycosides of N-acetylneuraminic acid methyl ester were transformed by successive treatment with dimethyl(methylthio)sulfonium triflate (DMTST) and 1,8-diazabicyclo[5.4.0]-7- undecene (DBU) to give the corresponding methyl 2-deoxy-2,3- didehydroneuraminates in excellent yields. Their acids and their analogues are sialidase inhibitors of pharmaceutical interest.
Chemoenzymatic synthesis of sialylated oligosaccharides for their evaluation in a polysialyltransferase assay
Sengupta, Prabal,Misra, Anup Kumar,Suzuki, Misa,Fukuda, Minoru,Hindsgaul, Ole
, p. 6037 - 6042 (2003)
A series of sialylated β-D-Gal-(1→3)-α-D-GalNAc-octyl containing oligosaccharides representative of those found on mucin type complex O-glycans were synthesized by a chemoenzymatic approach for use in the kinetic characterization of recently cloned polysialyltransferases. Enzymatic incorporation of N-acetylneuraminic acid (sialic acid) into the synthetic acceptors was accomplished by 2,3-(N) and (O)-sialyltransferases to give the target compounds 6-10 in a practical yield.
Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis
Horn, Evan J.,Gervay-Hague, Jacquelyn
, p. 4357 - 4359 (2009)
Peracetylated Neu5Ac2en methyl ester, an intermediate in the synthesis of the influenza neuraminidase inhibitor Relenza, has been synthesized in high yields from peracetylated Neu5Ac methyl ester by flash vacuum pyrolysis. Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.
Donor-Reactivity-Controlled Sialylation Reactions
Asressu, Kesatebrhan Haile,Chang, Chun-Wei,Lam, Sarah,Wang, Cheng-Chung
, p. 4525 - 4530 (2021/08/09)
Although tremendous efforts have been made for the efficient preparation of sialosides, controlling the stereochemical outcome of sialylation reaction still remains one of the most challenging tasks due to the unique chemical structure of sialic acid. We developed a new strategy to statistically analyze the stereoselectivity of sialylation reactions on six types of p-tolyl thiosialosides in NIS/TfOH system using Relative Reactivity Value (RRV) as the indicator. Analysis of the reaction mechanism showed the formation of the relatively stable glycosyl bromide and glycosyl chloride intermediates from halide- and triflate-containing promotors in the absence of an acceptor. We found that the α/β-stereoselectivity, yields, and intermediate changes were associated with their donor reactivity. These findings enable to tailor the most suitable building blocks for stereo-controlled sialylation reactions.
Facile anomer-oriented syntheses of 4-methylumbelliferyl sialic acid glycosides
Hassan, Abdullah A.,Oscarson, Stefan
supporting information, p. 6644 - 6649 (2021/08/10)
As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared fromN-acetylneuraminic acid. Both α- and β-4-methylumbelliferyl sialic acid glycosides were prepared in high yields and stereoselectivity. α-Anomers were accessedviareagent control by utilising additive CH3CN and TBAI, whereas the β-anomers were synthesised through a diastereoselective addition reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation of novel sialidases.
Synthesis of the sialylated pentasaccharide repeating unit of the capsular polysaccharide of Streptococcus group B type VI
Manna, Tapasi,Misra, Anup Kumar
, (2021/03/29)
An efficient synthetic strategy has been developed for the synthesis of the sialic acid containing pentasaccharide repeating unit of the cell wall O-antigen of Streptococcus group B type VI strain involving stereoselective α-glycosylation of sialic acid thioglycoside derivative. Stereoselective glycosylation of glycosyl trichloroacetimidate derivatives and thioglycosides were carried out using perchloric acid supported over silica (HClO4–SiO2) as a solid acid catalyst. A panel of sialic acid donors has been screened for achieving satisfactory yield and stereochemical outcome of the glycosylation reaction.
One pot synthesis of thio -glycosides via aziridine opening reactions
Hribernik, Nives,Tamburrini, Alice,Falletta, Ermelinda,Bernardi, Anna
supporting information, p. 233 - 247 (2021/01/14)
A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.
