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Volumn 71, Issue 22, 2006, Pages 8424-8430

New bioorganic reagents: Evolved cyclohexanone monooxygenase - Why is it more selective?

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPOSITION; ENZYMES; MUTAGENS; ORGANIC COMPOUNDS; OXIDATION;

EID: 33750594766     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061349t     Document Type: Article
Times cited : (41)

References (38)
  • 16
    • 33750586198 scopus 로고    scopus 로고
    • note
    • tert-Butylcyclohexanone was accepted by an isolated enzyme with low conversion (17%) but very high enantiomeric excess (98%) (ref 15).
  • 18
    • 0001117813 scopus 로고
    • Ichihara, A.; Miki, S.; Kawagishi, H.; Sakamura, S. Tetrahedron Lett. 1989, 30, 4551-4554. Unfortunately, this paper failed to provide spectroscopic characteristics and the specific rotation of the putative (R) lactone.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4551-4554
    • Ichihara, A.1    Miki, S.2    Kawagishi, H.3    Sakamura, S.4
  • 29
  • 37
    • 0036841620 scopus 로고    scopus 로고
    • and neither is spirol[5.5]-undecan-3-one (ref 7)
    • For example, 1.4-dioxaspirol[4.5]decan-8-one is not a substrate for CHMO (Iwaki, H.; Hasegawa, Y.; Wang, S.; Kayser, M. M.; Lau, P. C. K. Appl. Environ. Microbiol. 2002, 68, 5671-5684), and neither is spirol[5.5]-undecan-3-one (ref 7). Halogen-substituted substrates might not fit into the active sites in their axial conformation because of the long carbon-halogen bonds (C-Cl (1.77 Å), C-Br (1.94 Å) vs C-C (1.54 Å)).
    • (2002) Appl. Environ. Microbiol. , vol.68 , pp. 5671-5684
    • Iwaki, H.1    Hasegawa, Y.2    Wang, S.3    Kayser, M.M.4    Lau, P.C.K.5
  • 38
    • 0030091378 scopus 로고    scopus 로고
    • NMR results (ref 32) estimate that for 4-methoxycyelohexanone the axial conformation is favored by approximately 0.5 kcal/mol. In the calorimetric studies, the hydrogen-bonded interaction OH⋯O is given as 4.8 kcal/mol (Letcher, T. L.; Bricknell, B. C. J. Chem. Eng. Data 1996, 41, 166-169). In view of that, we may expect that even a relatively weak (long) H-bond will determine the conformation of the reacting 4-methoxycyclohexanone.
    • (1996) J. Chem. Eng. Data , vol.41 , pp. 166-169
    • Letcher, T.L.1    Bricknell, B.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.