The Library
STRUCTURES AND STEREOCHEMICAL ASSIGNMENTS OF SOME NOVEL CHIRAL SYNTHONS DERIVED FROM THE BIOTRANSFORMATION OF 2,3-DIHYDROBENZOFURAN AND BENZOFURAN BY PSEUDOMONAS-PUTIDA
Tools
UNSPECIFIED (1993) STRUCTURES AND STEREOCHEMICAL ASSIGNMENTS OF SOME NOVEL CHIRAL SYNTHONS DERIVED FROM THE BIOTRANSFORMATION OF 2,3-DIHYDROBENZOFURAN AND BENZOFURAN BY PSEUDOMONAS-PUTIDA. TETRAHEDRON-ASYMMETRY, 4 (6). pp. 1307-1324. ISSN 0957-4166.
Research output not available from this repository.
Request-a-Copy directly from author or use local Library Get it For Me service.
Abstract
Metabolism of 2,3-dihydrobenzofuran using intact cells of Pseudomonas puyida UV4 gave mainly (3S)-3-hydroxy-2,3-dihydrobenzofuran which was in tum oxidized to an unstable intermediate, (3S,4R,5S)-3,4,5-trihydroxy-2,3,4,5-tetrahydrobenzofuran. Spontaneous dehydration of this cis,cis-triol occurred in the carbocyclic ring to give (3S)-3,5-dihydroxy 2,3-dihydrobenzofuran and in the heterocyclic ring to yield (4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran. Bacterial metabolism of benzofuran was found to occur in the carbocyclic ring to form (6S,7S)-cis-6,7-dihydroxy-6,7-dihydrobenzofuran and its dehydration product, 6-hydroxybenzofuran. Dioxygenase-catalysed cis-dihydrodiol formation in the heterocyclic ring of benzofuran (to give cis-2,3-dihydroxy-2,3-dihydrobenzofuran as a transient intermediate) is proposed to account for the appearance of (1R)-1,2-dihydroxy-1-(2'-hydroxyphenyl)ethane as a major metabolite of benzofuran. cis-4,5-Dihydroxy-4,5-dihydrobenzofuran and cis-6,7-dihydroxy-6,7-dihydrobenzofuran are potentially valuable chiral synthons which can be added to the small pool of bicyclic cis-dihydrodiol metabolites currently available for synthesis.
Item Type: | Journal Article | ||||
---|---|---|---|---|---|
Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON-ASYMMETRY | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0957-4166 | ||||
Official Date: | June 1993 | ||||
Dates: |
|
||||
Volume: | 4 | ||||
Number: | 6 | ||||
Number of Pages: | 18 | ||||
Page Range: | pp. 1307-1324 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
Request changes or add full text files to a record
Repository staff actions (login required)
View Item |