Solid-Phase Peptide Synthesis of Arginine-vasopressin with Amide Side-chain of Asparagine Protected with 1-Tetralinyl Group

Amir Yusuf, Peter Gitu, Bhalendu Bhatt, Martin Njogu, Ali Salim, Duke Orata

Abstract


Arginine-vasopressin, 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, tetralinyl and tosyl groups were used in the protection of glutamine, asparagine and arginine side-chains respectively. TFMSA-TFA-thioanisole-1,2-ethanedithiol (2:20:2:1 v/v) was used to cleave the peptide from  the resin under different conditions to obtain arginine-vasopressin in a one-pot reaction. The cleavage at 40°C for two hours gave arginine-vasopressin quantitatively (77% yield)

Keywords: Solid-Phase Peptide Synthesis, resin, protecting group, cleavage, nonapeptide

 


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ISSN (Paper)2224-3224 ISSN (Online)2225-0956

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