9-O-Sulfation on α-NeuAc-(2→8)-NeuAc and inter-residue lactonization

An Tai Wu, Yi Ping Yu, Chien Tai Ren, Wei Zou, Shih Hsiung Wu

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1 Citation (Scopus)

Abstract

Treatment of α-NeuAc-(2→8)-NeuAc (1) with SO3- pyridine (4 equiv) in DMF resulted in selective 9-O-sulfation on the nonreducing end residue and the formation of an inter-residual δ-lactone. The lactonization could result from the C-2 carboxylic acid of the nonreducing residue condensing with the hydroxyl group or/and sulfated group at C-9 of the reducing residue to form a six-membered ring between two adjacent sialic acid residues. When α-NeuAc-(2→9)-NeuAc (5) was used as a sulfation substrate, only 9-O-sulfation on the nonreducing end residue was observed. According to capillary electrophoresis (CE) analysis, 9-O-sulfation on the disialic acid is a fast reaction, while sulfation on other hydroxyl groups is insignificant under the conditions used.

Original languageEnglish
Pages (from-to)1219-1223
Number of pages5
JournalCarbohydrate Research
Volume340
Issue number6
DOIs
Publication statusPublished - 2005 May 2

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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