Solid-phase peptide synthesis of isotocin with amide of asparagine protected with 1-tetralinyl. Rifluoromethanesulphonic acid (tfmsa) deprotection, cleavage and air oxidation of mercapto groups to disulphide
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Date
2001Author
Amir, O. Yusuf
Bhatt, Bhalendu M
Gitu, Peter M
Type
ArticleLanguage
enMetadata
Show full item recordAbstract
Isotocin, a nonapept ide amide, was synthesised on a benzhydryl-resin using the Bocst
rat egy. Benzyl group was used in the pr otect ion of the side-ch ains of tyrosine, ser ine and cyst eine.
Tetr alinyl group was used to protect aspar agine side-chain. TFMSA-TFA-thioanisole-1,2-
ethanedithiol (2:20:2:1 v/v) was used on the pept ide-r esin under different cleavage conditions to
obtain isotocin in a one-pot rea ct ion. The cleavage at 40 °C for two hours gave isotocin quantitatively.
Isotocin could be isolated in 61% yield.
Citation
Bu ll. Chem. Soc. Eth iop. 2001, 15(2), 143-149.Publisher
Department of Chemistry, University of Nairobi