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Volumn 15, Issue 15, 2004, Pages 2345-2350

A drop of enantioselectivity in the Pseudomonas cepacia lipase-catalyzed ester hydrolysis is influenced by the chain length of the fatty acid

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ESTER; FATTY ACID; TRIACYLGLYCEROL LIPASE;

EID: 4143088537     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.06.010     Document Type: Article
Times cited : (7)

References (26)
  • 1
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    • (2002) J. Biotech. , vol.96 , pp. 23-33
    • Colombo, G.1    Carrea, G.2
  • 3
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    • and references cited therein
    • Bornscheuer U.T. Curr. Opin. Biotech. 13:2002;543-547. and references cited therein
    • (2002) Curr. Opin. Biotech. , vol.13 , pp. 543-547
    • Bornscheuer, U.T.1
  • 12
    • 0003519413 scopus 로고    scopus 로고
    • Bioorganic Chemistry. A Chemical Approach to Enzyme Action
    • New York: Springer. Chapter 4
    • Dugas H. Bioorganic Chemistry. A Chemical Approach to Enzyme Action. 3rd ed.:1996;Springer, New York. Chapter 4
    • (1996) 3rd Ed.
    • Dugas, H.1
  • 13
    • 4143110022 scopus 로고    scopus 로고
    • note
    • 2,4a have been completely avoided furnishing an original solution to the challenging task of the energy evaluation of enzyme-substrate complexes
  • 18
    • 4143107784 scopus 로고    scopus 로고
    • The software package InsightII of Accelrys, San Diego, CA, USA was used to perform the graphics manipulations
    • The software package InsightII of Accelrys, San Diego, CA, USA was used to perform the graphics manipulations
  • 20
    • 4143137380 scopus 로고    scopus 로고
    • note
    • 15 When a few of these geometries were transformed into the corresponding THI's and relaxed, an anti-conformation of the alcoholic moiety was detected, probably due to propagation of the perturbation caused by the rearrangement of the acyl chain into HA. Such a gauche-anti conformational interconversion, if real, would be even more effective in slowing down the reaction speed of the fast-reacting enantiomer in light of the stereoelectronic theory requirements (see the third column of Table 2). A similar overall picture - not discussed in the text - was obtained too, when the hydrolysis of 1e was simulated
  • 22
    • 4143125363 scopus 로고    scopus 로고
    • note
    • The ΔE values reported in the second column of Table 2 suggest a steady preference of PcL towards the (R)-enantiomers of the primary alcohols during the recognition step. The trend of these data - related to the experimentally observed drop of enantioselectivity - could be interpreted as a further sign that lipase enantioselectivity does not come into play during the recognition process


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.