The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
ISOLATION AND IDENTIFICATION OF S-PROPYLIDENE-Δ1-PYRROLINE-S-CARBOXYLIC ACID, A BIOSYNTHETIC PRECURSOR OF LINCOMYCIN
M. S. KUOD. A. YUREKJ. H. COATSS. T. CHUNGG. P. LI
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JOURNAL FREE ACCESS

1992 Volume 45 Issue 11 Pages 1773-1777

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Abstract

An accumulated lincomycin intermediate in UC 8292, a lincomycin nonproducing strain of Streptomyces lincolnensis, has been isolated and purified by employing an assay system based on complementation of UC 11066, another lincomycin nonproducing strain of S. lincolnensis. The structure of the purified intermediate is shown to be 3-propylidene-Δ1-pyrroline-5-carboxylic acid, or 1, 2, 3, 6-tetradehydro-propylproline by mass spectrometry and NMR spectroscopic studies. Based on the structure of this newly found intermediate, a biosynthetic pathway for propylproline is proposed as tyrosine→L-3-hydroxytyrosine (Dopa)→→→→3-propylidene-Δ1-pyrroline-5-carboxylic acid→3-propyl-Δ2-pyrroline-5-carboxylic acid→propylproline.

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© Japan Antibiotics Research Association
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