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

Research output: Contribution to journalArticle

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

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Hydroxyl Radical
Capillary electrophoresis
Capillary Electrophoresis
N-Acetylneuraminic Acid
Lactones
Carboxylic Acids
Acids
Substrates
pyridine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Wu, An Tai ; Yu, Yi Ping ; Ren, Chien Tai ; Zou, Wei ; Wu, Shih Hsiung. / 9-O-Sulfation on α-NeuAc-(2→8)-NeuAc and inter-residue lactonization. In: Carbohydrate Research. 2005 ; Vol. 340, No. 6. pp. 1219-1223.
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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.",
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9-O-Sulfation on α-NeuAc-(2→8)-NeuAc and inter-residue lactonization. / Wu, An Tai; Yu, Yi Ping; Ren, Chien Tai; Zou, Wei; Wu, Shih Hsiung.

In: Carbohydrate Research, Vol. 340, No. 6, 02.05.2005, p. 1219-1223.

Research output: Contribution to journalArticle

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AB - 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.

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