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

A novel N-acetylneuraminic acid analogue, 2-S-(5'-aminopentyl) 5-acetamido- 3,5-dideoxy-2-thio-D-glycero-alpha-D-galacto-2-nonulopyranosidonic acid, as well as the thiosialoside 2-S-(2'-aminoethyl) 5-acetamido-3,5-dideoxy-2-th io-D-glycero-alpha-D-galacto-2-nonulopyranosidonic acid, have been synthesi sed and successfully coupled to CNBr-activated Sepharose 4B through the ter minal amino group. The resultant affinity resins have proved efficient in p urifying a number of sialic acid-recognising proteins such as Vibrio choler ae sialidase, sialidase-l from leech, trans-sialidase from Trypanosoma cruz i, and sialyltransferases from rat liver, all in high yield. (C) 1999 Elsev ier Science Ltd. All rights reserved.