Journal
TETRAHEDRON
Volume 56, Issue 2, Pages 249-256Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)00946-1
Keywords
pyochelin; siderophores; thiazolines; thiazolidines
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A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyphenylthiazolinylthiazolidine type of siderophore common to most strains of Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'-(2-Hydroxyphenyl)-2'-thiazoline-4'-carbox-aldehyde, a key molecule involved in this synthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin. Under the conditions reported, epimerization at the C-4' center was considerably diminished. (C) 1999 Elsevier Science Ltd. All rights reserved.
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