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Volumn 11, Issue 5, 1999, Pages 1063-1066

Asymmetric hydrolysis of enol esters with two esterases from Marchantia polymorpha

Author keywords

[No Author keywords available]

Indexed keywords

ENOL ACETATE; ENOL ESTER; ESTER; ESTERASE; KETONE; UNCLASSIFIED DRUG;

EID: 0343566447     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00046-X     Document Type: Article
Times cited : (19)

References (34)
  • 1
    • 0011928573 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • (a) Tomioka, K.; Koga, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 2, p. 201.
    • (1983) Asymmetric Synthesis , vol.2 , pp. 201
    • Tomioka, K.1    Koga, K.2
  • 2
    • 0000434949 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • (b) Ender, D. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p. 275.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 275
    • Ender, D.1
  • 4
    • 0001129994 scopus 로고
    • (b) Fehr, C. Chimia 1991, 45, 253.
    • (1991) Chimia , vol.45 , pp. 253
    • Fehr, C.1
  • 25
    • 0343655665 scopus 로고    scopus 로고
    • note
    • Homogenates of the cultured cells of M. polymorpha in 100 mM phosphate buffer (pH 7.0) were centrifuged at 100 000 g to give a cell-free extract, which was treated with ammonium sulfate (60-80% satd) to give a crude enzyme preparation. Butyl-Toyopearl column chromatography of the crude enzyme preparation gave a good separation of the two different esterases. Further purification by chromatography on a diethylaminoethyl-Toyo-pearl column and then a Sephadex G-75 column gave homogeneous esterases as judged by SDS-PAGE: esterase I, molecular mass ca. 54 000, dimeric form composed of two identical 27 000 subunits; esterase II, molecular mass ca. 45 000, dimeric form composed of two identical 22 500 subunits.
  • 26
    • 0343655664 scopus 로고    scopus 로고
    • note
    • 8
  • 28
    • 0343220073 scopus 로고    scopus 로고
    • note
    • In a typical experiment 2-methylcyclohexanone enol acetate 1 (5 mg) and Triton X-100 (5 mg) were dissolved in 2 ml of the sodium phosphate buffer containing enzyme (pH 7.0). The mixture was shaken at 300 rpm and 35°C. After 0.5 h the reaction mixture was extracted with n-pentane and the product was identified by direct comparison with the authentic sample by GLC and GC-MS analyses. The other substrates (2-7) were subjected to the enzymatic hydrolysis by the same procedure. It was confirmed that neither non-enzymatic hydrolysis nor racemization of the product occurred under the incubation conditions.
  • 29
    • 0343655663 scopus 로고    scopus 로고
    • note
    • 288 +278 (c 0.15, MeOH). The CD data of the products (11, 15-17) could not be obtained due to the low transformation rate and the lack of the products.
  • 34
    • 0343655660 scopus 로고    scopus 로고
    • note
    • -1). Retention times for the products in the GLC were as follows: 8 and 15, 11.8 and 12.8 min; 9 and 16, 12.7 and 12.9 min; 10 and 17, 23.8 and 24.0 min; 11 and 18, 18.1 and 18.4 min; 12 and 19, 27.7 and 27.9 min; 13 and 20, 72.1 and 72.8 min; 14 and 21, 60.1 and 61.2 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.