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CLEAR: A novel family of highly cross-linked polymeric supports for solid-phase peptide synthesis

Kempe, Maria LU and Barany, George (1996) In Journal of the American Chemical Society 118(30). p.7083-7093
Abstract
Cross-Linked Ethoxylate Acrylate Resin (CLEAR) supports were prepared by radical copolymerization, either in the bulk or suspension mode, of the branched cross-linker trimethylolpropane ethoxylate (14/3 EO/OH) triacrylate (1) with one or more of allylamine (2), 2-aminoethyl methacrylate·HCl (3), poly(ethylene glycol-400) dimethacrylate (4), poly(ethylene glycol) ethyl ether methacrylate (5), and trimethylolpropane trimethacrylate (6). The resultant highly cross-linked copolymers by the bulk procedures were ground and sieved to particles, whereas the suspension polymerization procedure gave highly cross-linked spherical beaded supports. CLEAR polymeric supports showed excellent swelling properties in an unusually broad range of solvents,... (More)
Cross-Linked Ethoxylate Acrylate Resin (CLEAR) supports were prepared by radical copolymerization, either in the bulk or suspension mode, of the branched cross-linker trimethylolpropane ethoxylate (14/3 EO/OH) triacrylate (1) with one or more of allylamine (2), 2-aminoethyl methacrylate·HCl (3), poly(ethylene glycol-400) dimethacrylate (4), poly(ethylene glycol) ethyl ether methacrylate (5), and trimethylolpropane trimethacrylate (6). The resultant highly cross-linked copolymers by the bulk procedures were ground and sieved to particles, whereas the suspension polymerization procedure gave highly cross-linked spherical beaded supports. CLEAR polymeric supports showed excellent swelling properties in an unusually broad range of solvents, including water, alcohols, tetrahydrofuran, dichloromethane, and N,N-dimethylformamide. To demonstrate their usefulness for peptide synthesis, CLEAR supports were derivatized with an “internal reference” amino acid [norleucine] and a handle [5-(4-Fmoc-aminomethyl-3,5-dimethoxyphenoxy)valeric acid] and were tested for both batchwise and continuous-flow solid-phase syntheses of challenging peptides such as acyl carrier protein (65-74), retro-acyl carrier protein (74-65), and the 17-peptide human gastrin-I. Comparisons to commercially available supports, e.g., polystyrene, Pepsyn K, Polyhipe, PEG-PS, TentaGel, and PEGA were also carried out. CLEAR supports are entirely stable under standard conditions of peptide synthesis but are in some cases labile to certain strong bases. (Less)
Please use this url to cite or link to this publication:
author
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
118
issue
30
pages
7083 - 7093
publisher
The American Chemical Society
external identifiers
  • Scopus:0029778868
ISSN
1520-5126
DOI
10.1021/ja954196s
language
English
LU publication?
no
id
eacfaeb1-118f-4368-8733-1f3b8dd45b41 (old id 1516093)
date added to LUP
2009-12-17 09:33:29
date last changed
2016-10-13 04:42:48
@misc{eacfaeb1-118f-4368-8733-1f3b8dd45b41,
  abstract     = {Cross-Linked Ethoxylate Acrylate Resin (CLEAR) supports were prepared by radical copolymerization, either in the bulk or suspension mode, of the branched cross-linker trimethylolpropane ethoxylate (14/3 EO/OH) triacrylate (1) with one or more of allylamine (2), 2-aminoethyl methacrylate·HCl (3), poly(ethylene glycol-400) dimethacrylate (4), poly(ethylene glycol) ethyl ether methacrylate (5), and trimethylolpropane trimethacrylate (6). The resultant highly cross-linked copolymers by the bulk procedures were ground and sieved to particles, whereas the suspension polymerization procedure gave highly cross-linked spherical beaded supports. CLEAR polymeric supports showed excellent swelling properties in an unusually broad range of solvents, including water, alcohols, tetrahydrofuran, dichloromethane, and N,N-dimethylformamide. To demonstrate their usefulness for peptide synthesis, CLEAR supports were derivatized with an “internal reference” amino acid [norleucine] and a handle [5-(4-Fmoc-aminomethyl-3,5-dimethoxyphenoxy)valeric acid] and were tested for both batchwise and continuous-flow solid-phase syntheses of challenging peptides such as acyl carrier protein (65-74), retro-acyl carrier protein (74-65), and the 17-peptide human gastrin-I. Comparisons to commercially available supports, e.g., polystyrene, Pepsyn K, Polyhipe, PEG-PS, TentaGel, and PEGA were also carried out. CLEAR supports are entirely stable under standard conditions of peptide synthesis but are in some cases labile to certain strong bases.},
  author       = {Kempe, Maria and Barany, George},
  issn         = {1520-5126},
  language     = {eng},
  number       = {30},
  pages        = {7083--7093},
  publisher    = {ARRAY(0x92e0858)},
  series       = {Journal of the American Chemical Society},
  title        = {CLEAR: A novel family of highly cross-linked polymeric supports for solid-phase peptide synthesis},
  url          = {http://dx.doi.org/10.1021/ja954196s},
  volume       = {118},
  year         = {1996},
}