Abstract
Here we report the chemoenzymatic synthesis and recognition function of glycoconjugate polymers carrying nonreducing disaccharides [α-D- glucopyranosyl-(1-1)-α-D-glucopyranoside (trehalose) and α-D-galactopyranosyl-(1-1)-α-D-glucopyranoside (Gal-type trehalose)]. The lipase-catalyzed esterification of the disaccharides with divinyl sebacate is completely selective at the primary Glc 6-OH position of trehalose and at the Gal 6-OH position of Gal-type trehalose. The resultant vinyl esters can be polymerized to yield glycoconjugate polymers with poly(vinyl alcohol) backbones. The interactions of the glycoconjugate polymers with lectins (concanavalin A and Bandeiraera simplicifolia) are amplified because of the glycocluster effect. The polymer carrying pendant α-D- galactopyranosyl-(1-1)-α-D-glucopyranoside shows inhibition activity against Shiga toxin-1 based on a stereochemical structure similar to that of globosyl Gb2 disaccharide.
| Original language | English |
|---|---|
| Pages (from-to) | 4598-4606 |
| Number of pages | 9 |
| Journal | Journal of Polymer Science, Part A: Polymer Chemistry |
| Volume | 42 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - Sep 15 2004 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Polymers and Plastics
- Organic Chemistry
- Materials Chemistry
Cite this
Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides. / Miura, Yoshiko; Wada, Natsuko; Nishida, Yoshihiro; Mori, Hiroshi; Kobayashi, Kazukiyo.
In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 42, No. 18, 15.09.2004, p. 4598-4606.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides
AU - Miura, Yoshiko
AU - Wada, Natsuko
AU - Nishida, Yoshihiro
AU - Mori, Hiroshi
AU - Kobayashi, Kazukiyo
PY - 2004/9/15
Y1 - 2004/9/15
N2 - Here we report the chemoenzymatic synthesis and recognition function of glycoconjugate polymers carrying nonreducing disaccharides [α-D- glucopyranosyl-(1-1)-α-D-glucopyranoside (trehalose) and α-D-galactopyranosyl-(1-1)-α-D-glucopyranoside (Gal-type trehalose)]. The lipase-catalyzed esterification of the disaccharides with divinyl sebacate is completely selective at the primary Glc 6-OH position of trehalose and at the Gal 6-OH position of Gal-type trehalose. The resultant vinyl esters can be polymerized to yield glycoconjugate polymers with poly(vinyl alcohol) backbones. The interactions of the glycoconjugate polymers with lectins (concanavalin A and Bandeiraera simplicifolia) are amplified because of the glycocluster effect. The polymer carrying pendant α-D- galactopyranosyl-(1-1)-α-D-glucopyranoside shows inhibition activity against Shiga toxin-1 based on a stereochemical structure similar to that of globosyl Gb2 disaccharide.
AB - Here we report the chemoenzymatic synthesis and recognition function of glycoconjugate polymers carrying nonreducing disaccharides [α-D- glucopyranosyl-(1-1)-α-D-glucopyranoside (trehalose) and α-D-galactopyranosyl-(1-1)-α-D-glucopyranoside (Gal-type trehalose)]. The lipase-catalyzed esterification of the disaccharides with divinyl sebacate is completely selective at the primary Glc 6-OH position of trehalose and at the Gal 6-OH position of Gal-type trehalose. The resultant vinyl esters can be polymerized to yield glycoconjugate polymers with poly(vinyl alcohol) backbones. The interactions of the glycoconjugate polymers with lectins (concanavalin A and Bandeiraera simplicifolia) are amplified because of the glycocluster effect. The polymer carrying pendant α-D- galactopyranosyl-(1-1)-α-D-glucopyranoside shows inhibition activity against Shiga toxin-1 based on a stereochemical structure similar to that of globosyl Gb2 disaccharide.
UR - http://www.scopus.com/inward/record.url?scp=4544220852&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4544220852&partnerID=8YFLogxK
U2 - 10.1002/pola.20385
DO - 10.1002/pola.20385
M3 - Article
AN - SCOPUS:4544220852
VL - 42
SP - 4598
EP - 4606
JO - Journal of Polymer Science, Part A: Polymer Chemistry
JF - Journal of Polymer Science, Part A: Polymer Chemistry
SN - 0887-624X
IS - 18
ER -