On the Transformation of ( S )‐2‐Hydroxypropylphosphonic Acid into Fosfomycin in  Streptomyces fradiae —A Unique Method of Epoxide Ring Formation | Zendy

Woschek Anna | Zendy; Wuggenig Frank | Zendy; Peti Wolfgang | Zendy; Hammerschmidt Friedrich | Zendy

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On the Transformation of ( S )‐2‐Hydroxypropylphosphonic Acid into Fosfomycin in Streptomyces fradiae —A Unique Method of Epoxide Ring Formation

Author(s) -

Woschek Anna,

Wuggenig Frank,

Peti Wolfgang,

Hammerschmidt Friedrich

Publication year - 2002

Publication title -

chembiochem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.05

H-Index - 126

eISSN - 1439-7633

pISSN - 1439-4227

DOI - 10.1002/1439-7633(20020902)3:9<829::aid-cbic829>3.0.co;2-v

Subject(s) - chemistry , epoxide , stereochemistry , stereospecificity , streptomyces fradiae , hydrogen bond , aldehyde , fosfomycin , medicinal chemistry , organic chemistry , streptomyces , molecule , catalysis , antimicrobial , actinomycetales , biology , bacteria , genetics

(1 S ,2 S )‐ and (1 R ,2 S )‐2‐hydroxy‐[1‐D 1 ]propylphosphonic acid were synthesised from (1 S ,2 S )‐2‐benzyloxy‐[1‐D 1 ]propanol, which was obtained by horse liver alcohol dehydrogenase catalysed reduction of the corresponding aldehyde. When (1 S ,2 S )‐2‐hydroxy‐[1‐D 1 ]propylphosphonic acid was fed to Streptomyces fradiae, the deuterium was retained to the same extent in fosfomycin ( cis ‐epoxide) and its co‐metabolite tran s‐epoxide. Removal of the hydrogen (deuterium) atom from the C‐1 atom of deuterated 2‐hydroxypropylphosphonic acids is a stereospecific process (the hydrogen atom of ( S )‐2‐hydroxypropylphosphonic acid is pro‐ R ). The formation of the OC‐1 bond of fosfomycin occurs with net inversion of configuration, the formation of the OC‐1 bond of the trans‐ epoxide with net retention.

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