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Peptide synthesis by means of polymer-anchoredN-hydroxy compound. 1. Preparation of simple peptides

Reactive Polymers Ion Exchangers Sorbents
Publication Date
DOI: 10.1016/0167-6989(87)90084-5


Abstract 6-Acetamido-1-hydroxy-3-trifluoromethylindazole ( 5) was incorporated into either a Merrifield bead-type chloromethylated copolystyrene with 2% divinylbenzene or a chloromethylated polystyrene-polypropylene composite fiber-type polymer to obtain 7a and 8a, respectively. Deprotection of the tetrahydropyranyl group of 7a and 8a with hydrochloric acid afforded 7b and 8b, respectively. From 7b, the p-chlorobenzensulfonate 7d, the diphenylphosphate ester 7e, the diphenylphosphinate ester 7f and the bis(2-oxo-3-oxazolidinyl)phosphinate ester 7g of the above polymer-anchored 1-hydroxyindazole derivative 7b were synthesized and from 8b, the p-chlorobenzenesulfonate 8d was obtained. These compounds were examined in the synthesis of Z-Val-GlyOEt; the best result was obtained with 7d in N, N′-dimethylformamide. Other simple peptides were also synthesized with 7d in good yields. To test the applicability of this method further, compound 7d was used to synthesize an intermediate of the melanocyte stimulating hormone-release-inhibiting factor, Z-Pro-Leu-GlyOEt; the yield was comparable with that from the conventional solution method. Also described is the solvent effect on the peptide yield.

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