STRUCTURES AND STEREOCHEMICAL ASSIGNMENTS OF SOME NOVEL CHIRAL SYNTHONS DERIVED FROM THE BIOTRANSFORMATION OF 2,3-DIHYDROBENZOFURAN AND BENZOFURAN BY PSEUDOMONAS-PUTIDA
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 0957-4166Full text not available from this repository.
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|
|Number of Pages:||18|
|Page Range:||pp. 1307-1324|
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