Abstract:(S)-N-Boc-3-hydroxypiperidine is an important intermediate of the anticancer drug ibrutinib and is mainly synthesized by the asymmetric reduction catalyzed by ketoreductase coupled with glucose dehydrogenase at present. In this study, the coexpression recombinant strains E. coli/pET28-K-rbs-G with single promoter and E. coli/pETDuet-K-G with double promoters were first constructed for the coexpression of ketoreductase and glucose dehydrogenase in the same cell. Then, the catalytic efficiency of E. coli/pET28-K… Show more
“…For example, the KRED from Candida glabrata , co-expressed in E. coli with GDH from a Bacillus sp ., afforded 52b in >99% ee at >99% conversion. 136…”
Section: Scope In the Enantioselective Synthesis Of Chiral Alcoholsmentioning
confidence: 99%
“…132 (S)-N-Boc-3-hydroxypiperidine 52b is the key chiral intermediate in the synthesis of the anti-cancer drug, ibrutinib. [133][134][135][136] It is produced by KRED catalysed reduction of the prochiral ketone N-Boc-3-piperidone 52a (Scheme 24). For example, the KRED from Candida glabrata, co-expressed in E. coli with GDH from a Bacillus sp., afforded 52b in 499% ee at 499% conversion.…”
Section: Chiral Heterocyclic Alcoholsmentioning
confidence: 99%
“…For example, the KRED from Candida glabrata, co-expressed in E. coli with GDH from a Bacillus sp., afforded 52b in 499% ee at 499% conversion. 136 Scheme 21 The biosynthesis route to (R)-b-hydroxy carboxylic acids.…”
The use of engineered ketoreductases (KREDS), both as whole microbial cells and isolated enzymes, in the highly enantiospecific reduction of prochiral ketones is reviewed. The homochiral alcohol products are key...
“…For example, the KRED from Candida glabrata , co-expressed in E. coli with GDH from a Bacillus sp ., afforded 52b in >99% ee at >99% conversion. 136…”
Section: Scope In the Enantioselective Synthesis Of Chiral Alcoholsmentioning
confidence: 99%
“…132 (S)-N-Boc-3-hydroxypiperidine 52b is the key chiral intermediate in the synthesis of the anti-cancer drug, ibrutinib. [133][134][135][136] It is produced by KRED catalysed reduction of the prochiral ketone N-Boc-3-piperidone 52a (Scheme 24). For example, the KRED from Candida glabrata, co-expressed in E. coli with GDH from a Bacillus sp., afforded 52b in 499% ee at 499% conversion.…”
Section: Chiral Heterocyclic Alcoholsmentioning
confidence: 99%
“…For example, the KRED from Candida glabrata, co-expressed in E. coli with GDH from a Bacillus sp., afforded 52b in 499% ee at 499% conversion. 136 Scheme 21 The biosynthesis route to (R)-b-hydroxy carboxylic acids.…”
The use of engineered ketoreductases (KREDS), both as whole microbial cells and isolated enzymes, in the highly enantiospecific reduction of prochiral ketones is reviewed. The homochiral alcohol products are key...
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