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New Useful Reagents for Peptide Synthesis. Insoluble Active Esters of Polystyrene-Bound 1-hydroxybenzotriazole

New Useful Reagents for Peptide Synthesis. Insoluble Active Esters of Polystyrene-Bound 1-hydroxybenzotriazole

R Kalir, A Warshawsky, M Fridkin, A Patchornik

Eur J Biochem. 1975 Nov 1;59(1):55-61.

PMID: 1204619

Abstract:

Insoluble 1-hydroxbenzotriazole-bound polystyrene was prepared through a series of chemical modifications of commercially available polystyrene. Reaction of 3-nitro-4-chlorobenzyl alcohol or of 3-nitro-4-chlorobenzyl bromide with polystyrene in the presence of aluminium trichloride yielded (3-nitro-4-chloro)benzylated polystyrene. Upon reaction with hydrazine it was converted to (3-nitro-4-hydrazine) benzylated polystyrene which was cyclized, by acidolysis, to yield 1-hydroxybenzotriazole-bound polystyrene. This was coupled, using N, N' -dicyclohexylcarbodiimide as the coupling agent, to many N-blocked amino acid derivatives, yielding polymeric polystyrene-bound active esters. Such derivatives are highly reactive and their efficacy in the synthesis of several peptides, including that of the tetrapeptide Boc-L-Leu-L-leu-L-Val-0bzl-L-Tyr-0Bzl and of thyrotropin-releasing hormone was demonstrated.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP873767	4-Chlorobenzyl alcohol		873-76-7	Price

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