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Volumn 11, Issue 5, 2005, Pages 1392-1401

Aldol additions of dihydroxyacetone phosphate to N-Cbz-amino aldehydes catalyzed by L-fuculose-1-phosphate aldolase in emulsion systems: Inversion of stereoselectivity as a function of the acceptor aldehyde

Author keywords

Biotransformations; DHAP dependent aldolases; Enzyme catalysis; Iminocyclitols; Lyases

Indexed keywords

ALDEHYDES; AMINO ACIDS; BONDING; CATALYSTS; EMULSIONS; ENZYMES; MATHEMATICAL MODELS; PHOSPHATES; REACTION KINETICS; STEREOCHEMISTRY; THERMODYNAMIC PROPERTIES;

EID: 14844302834     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400648     Document Type: Article
Times cited : (52)

References (46)
  • 2
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    • note
    • FucA was produced by the Department of Chemical Engineering, Universitat Autònoma de Barcelona, within the framework of a collaborative CYCIT project (PPQ2002-04625-CO2-01).
  • 14
    • 14844331689 scopus 로고    scopus 로고
    • note
    • 2 at 50 psi in the presence of 10% Pd/C. Aqueous solutions of each of the iminocyclitols in their free-base form were adjusted to pH 6.5, lyophilized, and submitted to NMR analysis without any further purification.
  • 15
    • 14844335644 scopus 로고    scopus 로고
    • note
    • In previous work (see ref. [7]), the relative configurations at the C-3 and C-4 positions of the linear structures 6-8 could not be unambiguously assigned by NMR analysis owing to overlapping signals resulting from the equilibria between the linear adducts and the corresponding cyclic hemiaminals. This was not the case with compound 5; less than 5% of the hemiaminal was formed and the proportion of both diastereoisomers of the linear compound could be determined.
  • 17
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    • W.-D. Fessner, G. Sinerius, A. Schneider, M. Dreyer, G. E. Schulz, J. Badia, J. Aguilar, Angew. Chem. 1991, 103, 596-599; Angew. Chem. Int. Ed. Engl. 1991, 30, 555-558.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 555-558
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    • W.-D. Fessner, A. Schneider, H. Held, G. Sinerius, C. Walter, M. Hixon, J. V. Schloss, Angew. Chem. 1996, 108, 2366-2369; Angew. Chem. Int. Ed. Engl. 1996, 35, 2219-2221.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2219-2221
  • 31
    • 14844320455 scopus 로고    scopus 로고
    • note
    • The stereochemistry of each chromatographic peak was identified by applying NMR techniques to purified samples of the major diastereoisomers and to diastereomeric mixtures of the minor ones.
  • 34
    • 14844304620 scopus 로고    scopus 로고
    • Kindly provided by G. E. Schulz and A. C. Joerger
    • Kindly provided by G. E. Schulz and A. C. Joerger.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.