1-Tetralinyl as carboxamine-protecting group for asparagine and application to N-a-t-Butyloxycarbonyl (Boc) solid-phase pentide synthesis of oxytocin

Citation:
Amir Y, Gitu P, Bhatt B, Njogu M, Salim A, Orata D. "1-Tetralinyl as carboxamine-protecting group for asparagine and application to N-a-t-Butyloxycarbonyl (Boc) solid-phase pentide synthesis of oxytocin." Chemistry and Materials Research. 2014.

Abstract:

Oxytocin, a nonapeptide amide, was synthesized on a benzhydryl-resin using the Boc strategy. Benzyl group was
used in the protection of sulfhydryl group of cysteine and tyrosine side-chain. Benzhydryl and tetralinyl groups were
used in the protection of glutamine and asparagine side-chains respectively. TFMSA-TFA-thioanisole-I,2-
ethanedithiol (2:20:2:1 v/v) was used on the peptide-resin under different cleavage conditions to obtain oxytocin in a
one-pot reaction. The cleavage at 40°C for two hours gave oxytocin quantitatively. Oxytocin could be isolated in
56% yield.

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