Abstract
The title dimethyl acetal 4 and related compounds can be efficiently synthesized by treatment of 6-caprolactone with commercially available dialkyl acetals. Conventional glucosylation using 4 as a glycosyl acceptor gave mainly β-glycosides which were deprotected to give 13. The latter was converted to the corresponding aldehyde 16, which was used as a hapten in conjugation, by reductive amination, to chicken serum albumin (CSA). Effect of reaction time, concentration and molar ratio of hapten 16 to the number of L-lysine residue in CSA upon incorporation of the hapten was studied using MALDI-TOF spectrometry. High loading of CSA with hapten, up to 22 moles of 16/CSA, could be achieved with 32% efficiency of utilization of the hapten. A glycoconjugate from a derivative, analogous to 16, of the monosaccharide determinant of the O-PS of Vibrio cholerae O:1, serotype Ogawa and CSA was also prepared. The achieved incorporation of the Vibrio cholerae hapten was in remarkable agreement with the value expected, based on the study with the D-glucose derivative.
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