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 language | English |
|---|---|
| Pages (from-to) | 1219-1223 |
| Number of pages | 5 |
| Journal | Carbohydrate Research |
| Volume | 340 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2005 May 2 |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
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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 journal › Article
TY - JOUR
T1 - 9-O-Sulfation on α-NeuAc-(2→8)-NeuAc and inter-residue lactonization
AU - Wu, An Tai
AU - Yu, Yi Ping
AU - Ren, Chien Tai
AU - Zou, Wei
AU - Wu, Shih Hsiung
PY - 2005/5/2
Y1 - 2005/5/2
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=15944401354&partnerID=8YFLogxK
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U2 - 10.1016/j.carres.2005.01.043
DO - 10.1016/j.carres.2005.01.043
M3 - Article
C2 - 15797139
AN - SCOPUS:15944401354
VL - 340
SP - 1219
EP - 1223
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 6
ER -