170452-85-4Relevant academic research and scientific papers
Facile anomer-oriented syntheses of 4-methylumbelliferyl sialic acid glycosides
Hassan, Abdullah A.,Oscarson, Stefan
, p. 6644 - 6649 (2021)
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.
Transsialidase from Trypanosoma cruzi for regio- and stereoselective synthesis of N-acyl-modified sialylated oligosaccharides and measurement of transfer rates
Schroven, Andreas,Meinke, Sebastian,Ziegelmueller, Patrick,Thiem, Joachim
, p. 9012 - 9021 (2008/09/16)
Recombinant transsialidase from Trypanosoma cruzi (TcTS) was used for the sialylation with natural and non-natural derivatives of neuraminic acid. Neu5Ac-α(2→3)-Gal-β(1→6)-Glc-αOMe was prepared in 80% yield. Correspondingly, the modified trisaccharide derivatives Neu5Prop-α(2 →3)-Gal-β(1 →6)-GlcαOMe (32%) and Neu5Gc-α(2→3)-Gal-β(1→6)-Glc-αOMe (Prop = propanoyl, Gc = glycolyl) were obtained in 60 % yield, respectively.
