A stereospecific carboxyl esterase from Bacillus coagulans hosting nonlipase activity within a lipase‐like fold

Abstract

Coordinates and structure factors have been deposited in the Protein Data Bank (www.rcsb.org) under accession numbers 5O7G (apo-BCE) and 5OLU (glycerol-bound BCE).

Overcoming Water Insolubility in Flow: Enantioselective Hydrolysis of Naproxen Ester

“…Following initial screening, HeE exhibited more activity against butyl esters (Table S1) similarly to BS2m previously reported to have a better activity with p-nitrophenyl butyrate [19]. BCE, on the other hand, had its maximum activity with ethyl esters [21]. Consequently, their ability to cleave NSAIDs derivative was assessed with butyl esters for the first two and with ethyl esters for BCE.…”

“…To better understand the applicability of carboxyl esterases for the hydrolysis of NSAIDs, three homologous enzymes were used for comparison. BS2m, an engineered versatile esterase from Bacillus subtilis [19,20], BCE from Bacillus coagulants with a mini-lid similarly to the one found in lipases [21] and HeE, a new esterase cloned form the halotolerant bacteria Halomonas elongata ( Figure S1).…”

“…In the present study, the enantioselective cleaving of naproxen and other NSAIDs ester derivatives with three different esterases was studied. BS2m from Bacillus subtilis and BCE from Bacillus coagulans were previously described [19][20][21], while HeE from Halomonas elongata is a novel enzyme. A comparison between the three active site architectures, paying particular attention to the tunnel leading to the catalytic site, has been reported.…”

Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis

“…Hydrolysis of 1a-b was firstly investigated using 20 commercial hydrolases and 15 enzymatic preparations from our laboratory [19][20][21][22][23][24]; only commercial PLE gave hydrolysis of 1a,b (Scheme 2) with conversions ranging between 50 and 100% after 24 hours (Table 1). Hydrolysis of 1a-b was firstly investigated using 20 commercial hydrolases and 15 enzymatic preparations from our laboratory [19][20][21][22][23][24]; only commercial PLE gave hydrolysis of 1a,b (Scheme 2) with conversions ranging between 50 and 100% after 24 h (Table 1). pharmaceutical applications as they can be useful chiral building blocks for the synthesis of compounds exerting muscarinic M3 receptor antagonist activity [16,17].…”

“…The synthesis of esters 1a-e, used in this work, was realized as described in Scheme 1. Hydrolysis of 1a-b was firstly investigated using 20 commercial hydrolases and 15 enzymatic preparations from our laboratory [19][20][21][22][23][24]; only commercial PLE gave hydrolysis of 1a,b (Scheme 2) with conversions ranging between 50 and 100% after 24 hours (Table 1). The reactions occurred with excellent rates, but low enantioselectivity, furnishing the S-acid with enantiomeric ratio (E) ranging between 8 and 10.…”