Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphthyl)ethanol (E ∼ 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E ∼ 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E ∼ 340), 2-(benzylthio)propanoic acid (E ∼ 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies.

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(S)-(−)-1-(6-Methoxy-2-naphthyl)ethanolC13H14O2Ee = 99% (HPLC analysis)[α]D25=-39.6 (c 0.8, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: S

(R)-(+)-1-(3,4-Methylenedioxyphenyl)ethanolC9H10O3Ee = 99% (HPLC analysis)[α]D25=+55.4 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: R

(S)-(−)-1-(3,4-Methylenedioxyphenyl)pentanolC12H16O3Ee = 98% (HPLC analysis)[α]D25=-61.9 (c 0.54, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: S

(S)-(−)-2-(6-Methoxy-2-naphthyl)propan-1-olC14H16O2Ee = 91.4% (HPLC analysis)[α]D25=-16.0 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: S

(S)-(+)-5-Bromo-6-methoxy-α-methyl-2-naphthaleneacetic acidC14H13BrO3Ee = 99% (HPLC analysis)[α]D25=+42.5 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: S

(S)-(+)-4-(2-Methylpropyl)-α-methylphenylacetic acidC13H18O2Ee = 99% (HPLC analysis)[α]D25=+51.4 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: S

(R)-(+)-2-(2-Naphthyloxy)propanoic acidC13H12O3Ee = 97% (HPLC analysis)[α]D25=+60.1 (c 1, CHCl3)Source of chirality: enzymatic hydrolysis and crystallizationAbsolute configuration: R

(R)-(+)-2-(Allylthio)propanoic acidC6H10O2SEe = 86% (specific rotation)[α]D25=+73 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: R

(R)-(+)-2-(n-Butylthio)propanoic acidC7H14O2SEe = 64% (specific rotation)[α]D25=+18.3 (c 0.9, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: R

(R)-(+)-2-(Phenylthio)propanoic acidC9H10O2SEe = 33.5% (specific rotation)[α]D25=+24.0 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: R

(R)-(+)-2-(Benzylthio)propanoic acidC10H12O2SEe = 99.7% (specific rotation)[α]D25=+129.1 (c 1, CHCl3)Source of chirality: enzymatic hydrolysisAbsolute configuration: R