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Mitigating base-catalysed degradation of periodate-oxidized capsular polysaccharides: Conjugation by reductive amination in acidic media.

Abstract：

:Reductive amination coupling an aldehyde-containing polysaccharide, generated by periodate oxidation, with the amino groups in protein has been widely used in the synthesis of glycoconjugate vaccines. The conjugation is often achieved under slightly basic conditions via a Schiff's base intermediate followed by its reduction with sodium cyanoborohydride. We observed that oxidized capsular polysaccharides such as Streptococcus pneumoniae type 6B (Pn-6B) and Haemophilus influenzae type a (HiA) underwent significant degradation during the conjugation in slightly basic media leading to sub-optimal glycoconjugates. Further study on oxidized Pn-3, Pn-6A, Pn-6C, Pn-2 polysaccharides and dextran provided evidence that the degradation is a result of base-catalysed β-elimination. In contrast to HiA, Pn-2, Pn-3, Pn-6B polysaccharides and dextran, oxidized Pn-6A and Pn-6C polysaccharides were stable under basic conditions due to lack of the leaving group at the β-position of the aldehyde. By performing conjugation of oxidized polysaccharides to bovine serum albumin (BSA) in phosphate buffer at pH 6.0, 6.8, 7.2 and 8.0, we concluded that the reductive amination proceeds best in slightly acidic media, particularly with those β-elimination susceptible polysaccharides.

journal_name

Vaccine

journal_title

Vaccine

authors

Zou W,Williams D,Cox A

doi

10.1016/j.vaccine.2018.12.072

subject

Has Abstract

pub_date

2019-02-14 00:00:00

pages

1087-1093

issue

8

eissn

0264-410X

issn

1873-2518

pii

S0264-410X(19)30053-2

journal_volume

37

pub_type

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