Effect of the α-methyl substituent on chemoselectivity in esterase-catalyzed hydrolysis of S-acetyl sulfanylalkanoates

Organic Letters

Volumn 1, Issue 2, 1999, Pages 207-209

  Kumar, Ish ^a   Jolly, Ravinder S ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE; ESTERASE; METHYL 3 (S ACETYLTHIO) 2 METHYLPROPANOATE; METHYL 3 (S ACETYLTHIO)BUTANOATE; METHYL 3-(S-ACETYLTHIO)-2-METHYLPROPANOATE; METHYL 3-(S-ACETYLTHIO)BUTANOATE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; HYDROLYSIS; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM;

BUTYRATES; CATALYSIS; ESTERASES; HYDROLYSIS; PROPIONATES; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM;

EID: 0033614868     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990544+     Document Type: Article

References (22)

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18. Preparation of esterase will be published elsewhere.
19. Representative Experiment. A suspension of 1 (0.440 g, 2.5 mM) in phosphate buffer (pH 7.00, 50 mL) was purged with a steam of nitrogen for 5 min, esterase (150 IU) was added, and the contents were stirred vigorously; the pH of the solution was kept at 7.00 by continues addition of 0.1 N aqueous NaOH. After 0.3 h, when there was no further drop in pH, the reaction mixture after acidification to pH 2.00 with dilute HCl was extracted with ether (3 × 10 mL). The organic extracts were washed with brine, dried (sodium sulfate), and then evaporated to give a mixture of acid 2 and the unchanged ester 1. The separation of acid and ester was effected by flash chromatography.
20. 3): δ 2.37 (s, 3H), 2.64 and 3.12 (each t, each 3H, J = 6.9 Hz), 3.68 (s, 3H).
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22. Thiol 4 was found to be very unstable and is rapidly converted into disulfide. It must therefore be isolated with care.