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Volumn 130, Issue 24, 2008, Pages 7655-7658

Opposite stereochemical courses for enzyme-mediated alkene reductions of an enantiomeric substrate pair

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS;

EID: 45249112780     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800200r     Document Type: Article
Times cited : (47)

References (37)
  • 4
    • 45249099941 scopus 로고    scopus 로고
    • Bougioukou, D. J. Ph.D. thesis, University of Florida, 2006.
    • Bougioukou, D. J. Ph.D. thesis, University of Florida, 2006.
  • 5
    • 45249086995 scopus 로고    scopus 로고
    • Formerly known as Saccharomyces carlsbergensis.
    • Formerly known as Saccharomyces carlsbergensis.
  • 25
    • 45249100191 scopus 로고    scopus 로고
    • Cis-2 was the major product of these conversions (>90%). A control reaction showed that cis-2 isomerized non-enzymatically to a mixture heavily favoring trans-4 under the reaction conditions, and this eroded the stereochemical purity of the product, particularly when long conversion times were required.
    • Cis-2 was the major product of these conversions (>90%). A control reaction showed that cis-2 isomerized non-enzymatically to a mixture heavily favoring trans-4 under the reaction conditions, and this eroded the stereochemical purity of the product, particularly when long conversion times were required.
  • 26
    • 45249102189 scopus 로고    scopus 로고
    • Attempts to carry out these reactions using only GST-Ltb4dh and excess NADPD in D2O were complicated by subsequent non-enzymatic epimerization of cis-2 (see ref 25, which resulted in complex NMR spectra. See Supporting Information for details of these experiments. We did not detect (R, or (S)-perillyl alcohol during these studies; (R)-perillyl alcohol could be detected only when (R)-1 GST-Ltb4dh was ommitted from the reaction mixtures. Whether TBADH could reduce trans-4 was not investigated since this product was not formed at significant levels during these experiments
    • 2O were complicated by subsequent non-enzymatic epimerization of cis-2 (see ref 25), which resulted in complex NMR spectra. See Supporting Information for details of these experiments. We did not detect (R)- or (S)-perillyl alcohol during these studies; (R)-perillyl alcohol could be detected only when (R)-1 GST-Ltb4dh was ommitted from the reaction mixtures. Whether TBADH could reduce trans-4 was not investigated since this product was not formed at significant levels during these experiments.
  • 27
    • 45249096447 scopus 로고    scopus 로고
    • We considered the possibility that NADPH occupied different binding sites for (R)- and (S)-perillaldehyde highly unlikely, given the many protein-cofactor contacts observed in the crystal structure of guinea pig Ltb4dh. These are likely conserved in the rat homologue and would strongly constrain the cofactor to its observed position.
    • We considered the possibility that NADPH occupied different binding sites for (R)- and (S)-perillaldehyde highly unlikely, given the many protein-cofactor contacts observed in the crystal structure of guinea pig Ltb4dh. These are likely conserved in the rat homologue and would strongly constrain the cofactor to its observed position.
  • 37
    • 45249114147 scopus 로고    scopus 로고
    • DeLano, W. L. The PyMOL Molecular Graphics System, 2002 (http://www.pymol.org).
    • (2002)
    • DeLano, W.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.