Synthesis of a Peptide Lactone, N-(3-Hydroxypicolinyl)-threonyl-d-leucyl-prolylsarcosyl-leucyl-alanyl-alanine Threonine Lactone
Open Access
- 1 January 1977
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 50 (1) , 280-284
- https://doi.org/10.1246/bcsj.50.280
Abstract
The synthesis of a peptide lactone, N-(3-hydroxypicolinyl)-threonyl-D-leucyl-prolylsarcosyl-leucyl-alanyl-alanine Threonine Lactone (21) is described. The t-butoxycarbonyl group of t-butyl O-(t-butoxycarbonyl-alanyl)-N-benzyloxycarbonyl-threonyl-D-leucyl-prolylsarcosinate (12) was deblocked selectively with formic acid in good yield. The coupling of 12 with the azide derived from t-butoxycarbonyl-leucyl-alanine hydrazide (15) with isopentyl nitrite gave a heptapeptide ester 17. Deblocking, cyclization, and hydrogenation gave a heptapeptide lactone 20 which was coupled with 3-hydroxypicolinic acid yielding 21Keywords
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