期刊
CHEMBIOCHEM
卷 5, 期 5, 页码 685-690出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.200300839
关键词
bioorganic chemistry; fluorine; NMR spectroscopy; stereochemistry
资金
- Biotechnology and Biological Sciences Research Council [BBS/B/04579] Funding Source: Medline
- Biotechnology and Biological Sciences Research Council [BBS/B/04579] Funding Source: researchfish
The stereochemical course of the recently isolated fluorination enzyme from Streptomyces cattleya has been evaluated. The enzyme mediates a reaction between fluoride ion and S-adenosyl-L-methionine (SAM) to generate 5'-fluoro-5'-deoxy-adenosine (5'-FDA). Preparation of (5'R)-[5-H-2(1)]-ATP generated (5'-R)-[5-H-2(1)]-5'-FDA in a coupled enzyme assay involving SAM synthase and the fluorinase. The stereochemical analysis of the product relied on H-2 NMR analysis in a chiral liquid-crystalline medium. It is concluded that the enzyme catalyses the fluorination with an inversion of configuration consistent with an S(N)2 reaction mechanism.
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