Solid-Phase Peptide Synthesis of Arginine-vasopressin with Amide Side-chain of Asparagine Protected with 1-Tetralinyl Group
Date
2014Author
Yusuf, Amir
Gitu, Peter
Bhatt, Bhalendu
Njogu, Martin
Salim, Ali
Orata, Duke
Type
ArticleLanguage
enMetadata
Show full item recordAbstract
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
Citation
Amir Yusuf, Peter Gitu, Bhalendu Bhatt, Martin Njogu, Ali Salim, Duke Orata (2014). Solid-Phase Peptide Synthesis of Arginine-vasopressin with Amide Side-chain of Asparagine Protected with 1-Tetralinyl Group. Chemistry and Materials Research, 6(4), 60-65.Publisher
University of Nairobi