The synthesis and evaluation of novel sialic acid analogues bound to matrices for the purification of sialic acid-recognising proteins

An investigation of the activity of recombinant rat skeletal muscle cytosolic sialidase

“…An affinity matrix derived from the neuraminic acid analogue 2-S-(aminoethyl) 5-acetamido-2-thio-D D-glycero-a-D D-galacto-2-nonulopyranosidonic acid was prepared using a previously described method [31,32]. The sialidase purification by affinity chromatography was performed at 4°C according to published methods [31,32].…”

“…The cDNA clone (pGEX-2T-SD) of rat muscle cytosolic sialidase was kindly provided by Dr. Taeko Miyagi (Miyagi Prefectural Cancer Centre, 47-1 Nodayama, Japan) and was expressed as previously described [4]. An affinity matrix derived from the neuraminic acid analogue 2-S-(aminoethyl) 5-acetamido-2-thio-D D-glycero-a-D D-galacto-2nonulopyranosidonic acid was prepared using a previously described method [31,32]. The sialidase purification by affinity chromatography was performed at 4°C according to published methods [31,32].…”

Recent Advances in the Synthesis of Sialic Acid Derivatives and Sialylmimetics as Biological Probes

“…The resulting matrix has proved valuable in the one-step purification of various sialidases. Similarly, the attachment through the terminal amine unit of a series of thiosialosides with varied aglycon chain lengths (e.g., 78 ) to CNBr-activated Sepharose 4B resulted in affinity matrixes suitable for purifying sialidases and sialyltransferases …”

The Chemistry of Sialic Acid

“…Von Itzstein and co-workers employed 2-thioacetyl Neu5Ac, which was deacetylated in situ with diethylamine and coupled with a sugar triflate to give the corresponding thioglycosides in good yields [296][297][298]. An S-alkylation strategy was employed to synthesize a 2-S-5'-aminopentenyl derivative, which was coupled to CNBr-activated Sepharose 4B through the terminal amino group [298,300]. The same group showed by NMR experiments that Neu5Ac-2-S-a-(2-6)Galb-OMe and Neu5Ac-2-Sa-(2-3)Galb-OMe are indeed stable towards the sialidase of Vibrio cholerae [299].…”