PHOTOLABILE MULTI‐DETACHABLE p‐ALKOXYBENZYL ALCOHOL RESIN SUPPORTS FOR PEPTIDE FRAGMENT OR SEMI‐SYNTHESIS
- 1 November 1980
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 16 (5) , 412-425
- https://doi.org/10.1111/j.1399-3011.1980.tb02965.x
Abstract
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 Nα‐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.Keywords
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