Protection of the amide side-chain of asparagine with the 1-tetralinyl group in the solid-phase peptide synthesis of lysine-vasopressin

Lysine-vasopressin, a nonapeptide, was synthesised on a benzhydryl-resin using solid-phase peptide synthesis via the Boc-strategy. The benzyl group was used in the protection of the side-chains of tyrosine and cysteine, while 1-tetralinyl, benzhydryl and benzyloxycarbonyl groups were used in the pro...

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Bibliographic Details
Published in:South African journal of chemistry 2002-01, Vol.55 (1), p.87-96
Main Authors: Yusuf, A.O., Gitu, P.M., Bhatt, B.M.
Format: Article
Language:English
Subjects:
1-tetralinyl
Amide protection
Benzhydryl-resin
Cyclic peptide
Electrospray mass spectrum
Solid-phase peptide synthesis
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Summary:Lysine-vasopressin, a nonapeptide, was synthesised on a benzhydryl-resin using solid-phase peptide synthesis via the Boc-strategy. The benzyl group was used in the protection of the side-chains of tyrosine and cysteine, while 1-tetralinyl, benzhydryl and benzyloxycarbonyl groups were used in the protection of the side-chains of asparagine, glutamine and lysine, respectively. Thioanisole-1, 2-ethanedithiol-trifluoroacetic acid-trifluoromethanesulphonic acid (2:1:20:2 v/v) was used to cleave the peptide-resin under different temperature conditions. The cleavage at 40 °C for two hours gave lysine-vasopressin in a one-pot reaction; the yield after reversed-phase HPLC purification was 62%.
ISSN:0379-4350