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Volumn 68, Issue 9, 2003, Pages 3546-3551

Enzymatic resolution of bicyclic 1-heteroarylamines using Candida antarctica lipase B

Author keywords

[No Author keywords available]

Indexed keywords

THERMAL RACEMIZATION;

EID: 0037414542     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026701r     Document Type: Article
Times cited : (61)

References (26)
  • 7
    • 0041152088 scopus 로고    scopus 로고
    • For a review describing the use of enzymes in organic solvents, see: Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2226-2254
    • Carrea, G.1    Riva, S.2
  • 9
    • 0029417196 scopus 로고
    • The selectivity of CALB for the (R)-enantiomer has been rationalized based on the crystal structure and modeling of the active site: Uppenberg, J.; Ohrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonsen, T.; Jones, T. A. Biochemistry 1995, 34, 16838-16851. An empirical rule has been proposed by Kazlauskas to explain stereochemical preference of several lipases: (a) Kazlauskas, R. J.; Weissfloch, A. N.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665. (b) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959-6969.
    • (1995) Biochemistry , vol.34 , pp. 16838-16851
    • Uppenberg, J.1    Ohrner, N.2    Norin, M.3    Hult, K.4    Kleywegt, G.J.5    Patkar, S.6    Waagen, V.7    Anthonsen, T.8    Jones, T.A.9
  • 10
    • 33751499686 scopus 로고
    • The selectivity of CALB for the (R)-enantiomer has been rationalized based on the crystal structure and modeling of the active site: Uppenberg, J.; Ohrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonsen, T.; Jones, T. A. Biochemistry 1995, 34, 16838-16851. An empirical rule has been proposed by Kazlauskas to explain stereochemical preference of several lipases: (a) Kazlauskas, R. J.; Weissfloch, A. N.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665. (b) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959-6969.
    • (1991) J. Org. Chem. , vol.56 , pp. 2656-2665
    • Kazlauskas, R.J.1    Weissfloch, A.N.2    Rappaport, A.T.3    Cuccia, L.A.4
  • 11
    • 0242528545 scopus 로고
    • The selectivity of CALB for the (R)-enantiomer has been rationalized based on the crystal structure and modeling of the active site: Uppenberg, J.; Ohrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonsen, T.; Jones, T. A. Biochemistry 1995, 34, 16838-16851. An empirical rule has been proposed by Kazlauskas to explain stereochemical preference of several lipases: (a) Kazlauskas, R. J.; Weissfloch, A. N.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665. (b) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959-6969.
    • (1995) J. Org. Chem. , vol.60 , pp. 6959-6969
    • Weissfloch, A.N.E.1    Kazlauskas, R.J.2
  • 22
    • 0242429820 scopus 로고    scopus 로고
    • note
    • This result correlates well with a previous report of the resolution of la under similar conditions, which found E = 66; see ref 11.
  • 23
    • 0036229349 scopus 로고    scopus 로고
    • Preparation of -(5,6,7,8-tetrahydroquinolin-8-yl)amine was recently reported: Uenishi, J.; Hamada, M. Synthesis 2002, 5, 625-630.
    • (2002) Synthesis , vol.5 , pp. 625-630
    • Uenishi, J.1    Hamada, M.2
  • 24
    • 0242681777 scopus 로고    scopus 로고
    • note
    • 1,2,3,4-Tetrahydro-1-naphthylamine was previously resolved with CALB using ethyl acetate (E = 14): Reeve, C. D. 1999 WO99/31264.
  • 25
    • 0242681752 scopus 로고    scopus 로고
    • note
    • (1-Naphthyl)ethylamine was previously resolved with CAL using ethyl acetate (E = 8): Reeve, C. D. 1999 WO99/31264.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.