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Volumn 49, Issue 13, 2010, Pages 2389-2392

Enantioselective intermolecular aldehyde-ketone cross-coupling through an enzymatic carboligation reaction

Author keywords

Absolute configuration; Asymmetric synthesis; Benzoin. Enzyme catalysis; Thiamine diphosphate

Indexed keywords

ENANTIOSELECTIVITY; ENZYMES; KETONES; SINGLE CRYSTALS; SUBSTRATES;

EID: 77952956848     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906181     Document Type: Article
Times cited : (75)

References (28)
  • 3
    • 85036741820 scopus 로고    scopus 로고
    • The enzymatic formation of acetolactate from the 2-ketoacid pyruvate has already been demonstrated (see Ref. [13]) but no ketones were used as substrates.
    • The enzymatic formation of acetolactate from the 2-ketoacid pyruvate has already been demonstrated (see Ref. [13]) but no ketones were used as substrates.
  • 18
    • 33750685322 scopus 로고    scopus 로고
    • The absolute configuration of (5)-acetolactate was determined by CD spectroscopy; see: The absolute configuration of (R)-PAC was determined by chiral-phase HPLC analysis with the (R)-PAC formed by ScPDC. The absolute configurations of (TJ)-Ia and (R)-2a were determined by optical rotation; see Refs. [16] and [17].
    • The absolute configuration of (5)-acetolactate was determined by CD spectroscopy; see: A. Baykal, S. Chakraborty, A. Dodoo, F. Jordan, Bioorg. Chem. 2006, 34, 380. The absolute configuration of (R)-PAC was determined by chiral-phase HPLC analysis with the (R)-PAC formed by ScPDC. The absolute configurations of (TJ)-Ia and (R)-2a were determined by optical rotation; see Refs. [16] and [17].
    • (2006) Bioorg. Chem. , vol.34 , pp. 380
    • Baykal, A.1    Chakraborty, S.2    Dodoo, A.3    Jordan, F.4
  • 21
    • 33750685322 scopus 로고    scopus 로고
    • The absolute configuration of (S)-acetoin was also determined by CD specroscopy; see
    • The absolute configuration of (S)-acetoin was also determined by CD specroscopy; see: A. Baykal, S. Chakraborty, A. Dodoo, F. Jordan, Bioorg. Chem. 2006, 34, 380.
    • (2006) Bioorg. Chem. , vol.34 , pp. 380
    • Baykal, A.1    Chakraborty, S.2    Dodoo, A.3    Jordan, F.4
  • 23
    • 85036770029 scopus 로고    scopus 로고
    • We have tested the recombinant enzymes benzaldehyde lyase (from Pseudomonas fluorescens; protein ID (NCBI): AAG02282.1), benzoylformate decarboxylase (from Pseudomonas putida; protein ID (NCBI): AAC15502.1), pyruvate decarboxylase (from Saccharomyces cerevisiae; protein ID (NCBI): CAA39398.1 and from Zymomonas mobitis; protein ID (NCBI): AAA27696.2), and PigD (from Serratia marcescens; C. Dresen, PhD Thesis, University of Freiburg, 2008) in combinations with aromatic, aliphatic and olefinic methyl- and trifluoromethyl ketones. No traces of aldehyde-ketone cross-coupling products were found.
    • We have tested the recombinant enzymes benzaldehyde lyase (from Pseudomonas fluorescens; protein ID (NCBI): AAG02282.1), benzoylformate decarboxylase (from Pseudomonas putida; protein ID (NCBI): AAC15502.1), pyruvate decarboxylase (from Saccharomyces cerevisiae; protein ID (NCBI): CAA39398.1 and from Zymomonas mobitis; protein ID (NCBI): AAA27696.2), and PigD (from Serratia marcescens; C. Dresen, PhD Thesis, University of Freiburg, 2008) in combinations with aromatic, aliphatic and olefinic methyl- and trifluoromethyl ketones. No traces of aldehyde-ketone cross-coupling products were found.
  • 24
    • 0001167066 scopus 로고
    • Two-step synthesis: 1 hydroboration of 3,4-dihydro-2H-pyran, according to
    • Two-step synthesis: 1) hydroboration of 3,4-dihydro-2H-pyran, according to: H. C. Brown, J. V. N. Vara Prasad, S.-H. Zee, J. Org. Chem. 1985, 50,1582;
    • (1985) J. Org. Chem. , vol.50 , pp. 1582
    • Brown, H.C.1    Prasad, J.V.N.V.2    Zee, S.-H.3
  • 25
    • 84989478646 scopus 로고
    • oxidation of tetrahydro-2H-pyran3-ol, according to
    • oxidation of tetrahydro-2H-pyran3-ol, according to: A. J. Mancuso, D. Swern et al., Synthesis 1981, 165.
    • (1981) Synthesis , pp. 165
    • Mancuso, A.J.1    Swern, D.2
  • 26
    • 85036748718 scopus 로고    scopus 로고
    • Compounds 7-10 were prepared by Williamson ether synthesis using the phenols or thiophenol and chloroacetone as reactants.
    • Compounds 7-10 were prepared by Williamson ether synthesis using the phenols or thiophenol and chloroacetone as reactants.
  • 28
    • 85036735669 scopus 로고    scopus 로고
    • CCDC 752572 (7a), and CCDC 752573 (13a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif
    • CCDC 752572 (7a), and CCDC 752573 (13a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.