Open AccessSynthesis of a Peptide Lactone,N-(3-Hydroxypicolinyl)-threonyl-D-leucyl-prolylsarcosyl-leucyl-alanyl-alanine Threonine Lactone
Author(s) -
Hideki Kinoshita,
Hiroshi Kotake
Publication year - 1977
Publication title -
bulletin of the chemical society of japan
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.145
H-Index - 99
eISSN - 1348-0634
pISSN - 0009-2673
DOI - 10.1246/bcsj.50.280
Subject(s) - chemistry , lactone , hydrazide , alanine , threonine , peptide , stereochemistry , azide , yield (engineering) , amino acid , organic chemistry , serine , biochemistry , enzyme , materials science , metallurgy
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 21