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Volumn 61, Issue 26, 1996, Pages 9344-9355

Atropisomeric flavoenzyme models with a modified pyrimidine ring: Syntheses, physical properties, and stereochemistry in the reactions with NAD(P)H analogs

Author keywords

[No Author keywords available]

Indexed keywords

5 DEAZAFLAVINE DERIVATIVE; PYRIMIDINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

EID: 0030460965     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961799t     Document Type: Article
Times cited : (41)

References (43)
  • 24
    • 85033167990 scopus 로고    scopus 로고
    • note
    • Only one enantiomer is shown in the scheme for convenience.
  • 26
    • 85033166434 scopus 로고    scopus 로고
    • note
    • Conditions for preparative chromatography of 1: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 3.5 mL/min; detection, UV 254 nm; retention times, 55.1 and 83.0 min: conditions for analytical chromatography of 1: column, CHIRALCEL OD (0.46 cm φ × 5 cm); eluent, ethanol; flow rate, 0.2 mL/min; detection, UV 254 nm; retention times, 11.3 and 16.7 min.
  • 27
    • 85033165208 scopus 로고    scopus 로고
    • note
    • Conditions for preparative chromatography of 2: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 4.0 mL/min; detection, UV 254 nm; retention times, 78.5 and 156 min: conditions for analytical chromatography of 2: column, CHIRALCEL OD (0.46 cm φ × 5 cm); eluent, ethanol; flow rate, 0.5 mL/min; detection, UV 254 nm; retention times, 7.6 and 14.1 min.
  • 28
    • 85033181521 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 29
    • 85033179087 scopus 로고    scopus 로고
    • note
    • Conditions for preparative chromatography of 19: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 1.5 mL/min; detection, UV 254 nm; retention times, 89.5 and 95.6 min: conditions for analytical chromatography of 19: column, CHIRALCEL OD (0.46 cm φ × 5 cm + 0.46 cm φ × 25 cm); eluent, ethanol; flow rate, 0.5 mL/min; detection, UV 254 nm; retention times, 23.7 and 29.1 min. The second fraction was obtained in >99% ee by repetition of the optical resolution.
  • 32
    • 85033176486 scopus 로고    scopus 로고
    • note
    • Although trifluoroacetic acid was also used as an acid catalyst, syn/anti ratio was unable to be determined, because BNAH was decomposed by the acid very quickly.
  • 36
    • 33845561800 scopus 로고
    • It has been confirmed that the conformation at the side-chain carbamoyl group does not affect stereochemistry of the reaction largely: Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036-7040.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 7036-7040
    • Ohno, A.1    Ikeguchi, M.2    Kimura, T.3    Oka, S.4
  • 41
    • 0006202778 scopus 로고
    • Wiley: New York
    • Kurzer, F. Organic Syntheses; Wiley: New York, 1963; Vol. IV, pp 49-51.
    • (1963) Organic Syntheses , vol.4 , pp. 49-51
    • Kurzer, F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.