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Volumn 125, Issue 21, 2003, Pages 6348-6349

Reversal of the apparent regiospecificity of NAD(P)H-dependent hydride transfer: The properties of the difluoromethylene group, a carbonyl mimic

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; DIFLUOROMETHYLENE; FLUORINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

EID: 0038175466     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021487+     Document Type: Article
Times cited : (130)

References (32)
  • 3
    • 33845282135 scopus 로고
    • 2 (The Chemist's Companion; Gordon, A. J., Ford, R. A., Eds.; John-Wiley: New York, 1987), one can estimate the net distance for an effective hydride transfer to be approximately 0.55 Å or less (see: Kreevoy, M. M.; Ostovic, D.; Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. 1986, 90, 3766).
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2226
    • Wu, Y.-D.1    Houk, K.N.2
  • 4
    • 12444287036 scopus 로고
    • Gordon, A. J., Ford, R. A., Eds.; John-Wiley: New York
    • 2 (The Chemist's Companion; Gordon, A. J., Ford, R. A., Eds.; John-Wiley: New York, 1987), one can estimate the net distance for an effective hydride transfer to be approximately 0.55 Å or less (see: Kreevoy, M. M.; Ostovic, D.; Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. 1986, 90, 3766).
    • (1987) The Chemist's Companion
  • 5
    • 33845376018 scopus 로고
    • 2 (The Chemist's Companion; Gordon, A. J., Ford, R. A., Eds.; John-Wiley: New York, 1987), one can estimate the net distance for an effective hydride transfer to be approximately 0.55 Å or less (see: Kreevoy, M. M.; Ostovic, D.; Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. 1986, 90, 3766).
    • (1986) J. Phys. Chem. , vol.90 , pp. 3766
    • Kreevoy, M.M.1    Ostovic, D.2    Truhlar, D.G.3    Garrett, B.C.4
  • 14
    • 0025980642 scopus 로고
    • The tfbD gene (Jiang, X.-M.; Neal, B.; Santiago, F.; Lee, S. J.; Romana, L. K.; Reeves, P. R. Mol. Microbiol. 1991, 5, 695) was amplified by the polymerase chain reaction (PCR) using the genomic DNA of Salmonella enterica LT2 as the template and was cloned into a pUC18 vector. Purification of the RfbD protein (TDP-L-rhamnose synthase) from the E. coli HB101-rfbD recombinant strain involved two chromatographic steps: DEAE-Sepharose and Mono Q.
    • (1991) Mol. Microbiol. , vol.5 , pp. 695
    • Jiang, X.-M.1    Neal, B.2    Santiago, F.3    Lee, S.J.4    Romana, L.K.5    Reeves, P.R.6
  • 15
    • 12444312197 scopus 로고    scopus 로고
    • note
    • The scheme and a brief discussion of the synthesis can be found in the Supporting Information.
  • 16
    • 12444288790 scopus 로고    scopus 로고
    • note
    • Because the natural substrate (1) has a β-configuration at the anomeric carbon, only the β-isomer of 8 should be recognized and processed by TDP-L-rhamnose synthase.
  • 17
    • 12444323280 scopus 로고    scopus 로고
    • note
    • 12
  • 22
    • 12444345116 scopus 로고    scopus 로고
    • note
    • Compound 9 was the predominant species derived mainly from the unreacted 8α, and no 10 and 11 were detected when the incubation was performed in the absence of enzyme.
  • 23
    • 12444254153 scopus 로고    scopus 로고
    • note
    • 19F NMR indicates that little of this intermediate was accumulated during turnover.
  • 26
    • 0003428791 scopus 로고
    • Wiley: New York, Chapter 1
    • (a) Jones, M., Jr., Moss, R. A., Eds. Carbenes; Wiley: New York, 1973; Vol. I, Chapter 1.
    • (1973) Carbenes , vol.1
    • Jones M., Jr.1    Moss, R.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.