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PHOTOLABILE MULTI‐DETACHABLE p ‐ALKOXYBENZYL ALCOHOL RESIN SUPPORTS FOR PEPTIDE FRAGMENT OR SEMI‐SYNTHESIS

1980; Wiley; Volume: 16; Issue: 5 Linguagem: Inglês

10.1111/j.1399-3011.1980.tb02965.x

0367-8377

James P. Tam, Richard D. DiMarchi, R. B. Merrifield,

Carbohydrate Chemistry and Synthesis

Two photolabile multi‐detachable alkoxybenzyl alcohol resins, 2‐[4‐(oxymethyl)phenoxy]propionyl‐resin 4 and 4‐[4‐(oxymethyl)phenoxymethyl]‐3‐nitrobenzamidomethyl‐resin 5 have been synthesized. Bpoc‐peptide attached to resin 4 or 5 when treated with 50% trifluoroacetic acid provided the free, unprotected peptide, but on photolysis gave Bpoc‐peptide p‐ hydroxybenzyl ester. Removal of the p‐ hydroxybenzyl ester in aqueous base or by oxidative work up gave a protected Bpoc‐peptide suitable for fragment synthesis at its C‐ terminus. However, methylation of the ester to Bpoc‐peptide p‐ methoxybenzyl ester followed by removal of the Bpoc‐group gave a protected peptide p‐ methoxybenzyl ester suitable for fragment coupling at its N‐ terminus. The efficacies of these resins were evaluated in the syntheses of a model tetrapeptide and an octapeptide by using N α ‐ Bpoc‐, Fmoc‐ and Nps‐amino acids. The use of 2‐thiopyridine with pyridinium hydrochloride as a new and efficient thiolytic reagent for the deprotection of the Nps‐group was studied.