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Influence of resin cross-linking on solid-phase chemistry

Influence of resin cross-linking on solid-phase chemistry
Influence of resin cross-linking on solid-phase chemistry
A range of PS-DVB resins were prepared by suspension polymerization with styrene, p-chloromethyl styrene, and DVB. Yields of polymerization increased (from 40% to almost 80%) with increasing cross-linking. The beads exhibited the expected swelling characteristics, with the 0.3% resin swelling to almost 9 times its dry volume in CHCl3, Kinetics of cleavage of the dye Methyl Red from the range of Rink linked resins showed rate enhancements of up to 500% between the 6.0 and the 0.3% cross-linked resins. Total synthesis of Kawaguchipeptin B was carried out on the resins, and their performance during the syntheses was investigated. Contrary to expectations, the purities of the cyclic peptide product increased with increasing resin cross-linking doubling from the 0.3-6.0% resin. A Suzuki reaction showed the half-lives of reaction increased with increasing resin cross-linking with an Ii-fold increase in half-life between the 0.3-2.7% resin. Surprisingly, we observed very little reaction in the case of the 3.0 and 6.0% cross-linked resins.
organic-synthesis, coupling reactions, kawaguchipeptin-b, peptide-synthesis, polymer supports, suspension, copolymerization, styrene
1520-4766
9-15
Rana, Sunil
16726f81-3e09-45e4-b07b-944e7679e8ca
White, Peter
536aaa93-447f-4103-ba6b-d424b51a5572
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
Rana, Sunil
16726f81-3e09-45e4-b07b-944e7679e8ca
White, Peter
536aaa93-447f-4103-ba6b-d424b51a5572
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900

Rana, Sunil, White, Peter and Bradley, Mark (2001) Influence of resin cross-linking on solid-phase chemistry. Journal of Combinatorial Chemistry, 3 (1), 9-15. (doi:10.1021/cc0000592).

Record type: Article

Abstract

A range of PS-DVB resins were prepared by suspension polymerization with styrene, p-chloromethyl styrene, and DVB. Yields of polymerization increased (from 40% to almost 80%) with increasing cross-linking. The beads exhibited the expected swelling characteristics, with the 0.3% resin swelling to almost 9 times its dry volume in CHCl3, Kinetics of cleavage of the dye Methyl Red from the range of Rink linked resins showed rate enhancements of up to 500% between the 6.0 and the 0.3% cross-linked resins. Total synthesis of Kawaguchipeptin B was carried out on the resins, and their performance during the syntheses was investigated. Contrary to expectations, the purities of the cyclic peptide product increased with increasing resin cross-linking doubling from the 0.3-6.0% resin. A Suzuki reaction showed the half-lives of reaction increased with increasing resin cross-linking with an Ii-fold increase in half-life between the 0.3-2.7% resin. Surprisingly, we observed very little reaction in the case of the 3.0 and 6.0% cross-linked resins.

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More information

Published date: 2001
Keywords: organic-synthesis, coupling reactions, kawaguchipeptin-b, peptide-synthesis, polymer supports, suspension, copolymerization, styrene

Identifiers

Local EPrints ID: 19604
URI: http://eprints.soton.ac.uk/id/eprint/19604
ISSN: 1520-4766
PURE UUID: 5918067d-76cd-436c-a3d3-d4beda554567

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Date deposited: 14 Feb 2006
Last modified: 15 Jul 2019 19:26

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