- Asymmetric synthesis of (-)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step
-
Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer.
- Marocco, Christian P.,Davis, Erik V.,Finnell, Julie E.,Nguyen, Phung-Hoang,Mateer, Scott C.,Ghiviriga, Ion,Padgett, Clifford W.,Feske, Brent D.
-
-
Read Online
- Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin
-
Phosphocarnitine was conveniently obtained from easily available diethyl 3-chloro-2-oxopropanephosphonates, followed by subsequent reduction, Mucor miehei lipase (IM) mediated resolution, amination and dealkylation. Candida antarctica lipase B (CALB) serv
- Wang, Ke,Zhang, Yonghui,Yuan, Chengye
-
-
Read Online
- Silicon Directed Asymmetric Synthesis of (1R,2S)-(-)-(1,2-Epoxypropyl)phosphonic Acid (Fosfomycin) from (S)-Lactaldehyde
-
The title compound is obtained in high diastereomeric purity based on the stereoselective addition of trimethylsilyldibenzylphosphite (TMSDBP) to O-triisopropylsilyloxy (S)-lactaldehyde.
- Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe,Panunzio, Mauro
-
p. 2127 - 2130
(2007/10/03)
-
- Process for the preparation of intermediates for the synthesis of fosfomycin
-
A process is described for the preparation of intermediates useful in the synthesis of Fosfomycin. More particularly, an enantioselective process is described for the preparation of derivatives of (1S,2S)-1,2-dihydroxypropyl-phosphonic acid of formula STR1 wherein R2 and R3 have the meanings reported in the specification.
- -
-
-
- Process for the preparation of intermediates for the synthesis of fosfomycin
-
A process is described for the preparation of intermediates useful in the synthesis of Fosfomycin. More particularly, an enantioselective process is described for the preparation of derivatives of (1S,2S)-1,2-dihydroxypropyl--phosphonic acid of formula wherein R2 and R3 have the meanings reported in the specification.
- -
-
-
- Process for the preparation of antibiotics
-
Intermediate compounds of formula wherein R and R1 are the same or different and each represents a lower alkoxy or a -N(R2)2 group and both R2, independently, represent a hydrogen atom or a lower alkyl; the carbon atoms marked by an asterisk are both in R or S configuration;, allow to obtain enantioselectively the antibiotic known as Fosfomycin by an epoxidation reaction, carried out in the one or two steps, and a hydrolysis reaction.
- -
-
-