Abstract
New hydrophilic poly(vinyl alcohol) (PVA-OH) resins were prepared by an inverse suspension polymerization using epichlorohydrin as a cross-linker. These novel resins swell in a variety of solvents commonly used in solid-phase organic synthesis, such as dicholomethane, dioxane, methanol, tetrahydrofuran, and dimethyl-formamide. In addition, PVA-OH shows excellent swelling in water. The cross-linked PVA-OH beads were functionalized with an aldehyde group and were tested as scavengers for primary amines in three different reactions: amide bond formation, reductive amination reaction, and urea formation. With 1-2 equiv of the PVA aldehyde resin, all the excess primary amines were successfully scavenged. The utility of PVA-OH resins as solid supports in mono- and dipeptide synthesis was also investigated using symmetrical anhydride and MSNT/MeIm (2,4,6-mesitylenesulfonyl-3-nitro-1,2,4-triazolide in the presence of 1-methylimidazol) methods.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 961-966 |
| Number of pages | 6 |
| Journal | Journal of Combinatorial Chemistry |
| Volume | 6 |
| Issue number | 6 |
| DOIs | |
| State | Published - Nov 2004 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Discrete Mathematics and Combinatorics
Cite this
Functionalized cross-linked poly(vinyl alcohol) resins as reaction scavengers and as supports for solid-phase organic synthesis. / Wang, Zheng; Luo, Juntao; Zhu, X. X.; Jin, Shujuan; Tomaszewski, Mirosław J.
In: Journal of Combinatorial Chemistry, Vol. 6, No. 6, 11.2004, p. 961-966.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Functionalized cross-linked poly(vinyl alcohol) resins as reaction scavengers and as supports for solid-phase organic synthesis
AU - Wang, Zheng
AU - Luo, Juntao
AU - Zhu, X. X.
AU - Jin, Shujuan
AU - Tomaszewski, Mirosław J.
PY - 2004/11
Y1 - 2004/11
N2 - New hydrophilic poly(vinyl alcohol) (PVA-OH) resins were prepared by an inverse suspension polymerization using epichlorohydrin as a cross-linker. These novel resins swell in a variety of solvents commonly used in solid-phase organic synthesis, such as dicholomethane, dioxane, methanol, tetrahydrofuran, and dimethyl-formamide. In addition, PVA-OH shows excellent swelling in water. The cross-linked PVA-OH beads were functionalized with an aldehyde group and were tested as scavengers for primary amines in three different reactions: amide bond formation, reductive amination reaction, and urea formation. With 1-2 equiv of the PVA aldehyde resin, all the excess primary amines were successfully scavenged. The utility of PVA-OH resins as solid supports in mono- and dipeptide synthesis was also investigated using symmetrical anhydride and MSNT/MeIm (2,4,6-mesitylenesulfonyl-3-nitro-1,2,4-triazolide in the presence of 1-methylimidazol) methods.
AB - New hydrophilic poly(vinyl alcohol) (PVA-OH) resins were prepared by an inverse suspension polymerization using epichlorohydrin as a cross-linker. These novel resins swell in a variety of solvents commonly used in solid-phase organic synthesis, such as dicholomethane, dioxane, methanol, tetrahydrofuran, and dimethyl-formamide. In addition, PVA-OH shows excellent swelling in water. The cross-linked PVA-OH beads were functionalized with an aldehyde group and were tested as scavengers for primary amines in three different reactions: amide bond formation, reductive amination reaction, and urea formation. With 1-2 equiv of the PVA aldehyde resin, all the excess primary amines were successfully scavenged. The utility of PVA-OH resins as solid supports in mono- and dipeptide synthesis was also investigated using symmetrical anhydride and MSNT/MeIm (2,4,6-mesitylenesulfonyl-3-nitro-1,2,4-triazolide in the presence of 1-methylimidazol) methods.
UR - http://www.scopus.com/inward/record.url?scp=9344246838&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=9344246838&partnerID=8YFLogxK
U2 - 10.1021/cc0499183
DO - 10.1021/cc0499183
M3 - Article
C2 - 15530125
AN - SCOPUS:9344246838
VL - 6
SP - 961
EP - 966
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 6
ER -