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Volumn 74, Issue 17, 2009, Pages 6691-6702

Mechanistic insights on the magnesium(II) ion-activated reduction of methyl benzoylformate with chelated NADH peptide β-lactam models

Author keywords

[No Author keywords available]

Indexed keywords

BINARY COMPLEXES; CHEMICAL EQUATIONS; ENANTIOSELECTIVE REDUCTION; METHYL BENZOYLFORMATE; NMR TECHNIQUES; PEPTIDE CHAIN; PEPTIDOMIMETICS; REACTION PATHWAYS; STRUCTURAL DIFFERENCES; TERNARY COMPLEX; TRANSITION STATE; TRIMETHYLSILYL;

EID: 69549086786     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901236d     Document Type: Article
Times cited : (25)

References (70)
  • 13
    • 69549153945 scopus 로고
    • For previous conformationally restricted NADH peptides, see: (a)
    • For previous conformationally restricted NADH peptides, see: (a) Baba, N.; Oda, J.; Inouye, Y. J. Chem. Soc., Chem. Commun. 1980, 815-817.
    • (1980) J. Chem. Soc., Chem. Commun. , pp. 815-817
    • Baba, N.1    Oda, J.2    Inouye, Y.3
  • 22
    • 0021097011 scopus 로고
    • According to the original Benner's model, this phenomenon would be caused by a "reverse anomeric effect" that is unlikely to occur in 1,4- dihydronicotinamides without N-glycosidic groups, see: (a)
    • According to the original Benner's model, this phenomenon would be caused by a "reverse anomeric effect" that is unlikely to occur in 1,4- dihydronicotinamides without N-glycosidic groups, see: (a) Nambiar, P. K.; Stauffer, D. M.; Kolodziej, P. A.; Benner, S. A. J. Am. Chem. Soc. 1983, 105, 5886-5890.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5886-5890
    • Nambiar, P.K.1    Stauffer, D.M.2    Kolodziej, P.A.3    Benner, S.A.4
  • 27
    • 0029048009 scopus 로고
    • 2+-mediated reduction of methyl benzoylformate with achiral dihydronicotinamide, see: (a)
    • 2+-mediated reduction of methyl benzoylformate with achiral dihydronicotinamide, see: (a) Toyooka, Y.; Matsuzawa, T.; Eguchi, T.; Kakinuma, K. Tetrahedron 1995, 51, 6459-6474.
    • (1995) Tetrahedron , vol.51 , pp. 6459-6474
    • Toyooka, Y.1    Matsuzawa, T.2    Eguchi, T.3    Kakinuma, K.4
  • 28
    • 0001483181 scopus 로고
    • For theoretical studies on conformational features of NADH analogues, see: (b)
    • For theoretical studies on conformational features of NADH analogues, see: (b) Donkersloot, M. C. A.; Buck, H. M. J. Am. Chem. Soc. 1981, 103, 6554-6558.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6554-6558
    • Donkersloot, M.C.A.1    Buck, H.M.2
  • 46
    • 0005143888 scopus 로고
    • For extendedNADHpeptide models, see: (a)
    • For extendedNADHpeptide models, see: (a) Endo, T.; Hayashi, Y.; Okawara, M. Chem. Lett. 1977, 391-394.
    • (1977) Chem. Lett. , pp. 391-394
    • Endo, T.1    Hayashi, Y.2    Okawara, M.3
  • 54
    • 69549152427 scopus 로고    scopus 로고
    • note
    • In the case of α-(2-methylnaphthyl)-β-lactams 6d and 6f a partial hydrogenation of the naphthalene moiety was observed and the corresponding 5,6,7,8-tetrahydronaphthyl derivatives were obtained.
  • 67
    • 69549098648 scopus 로고    scopus 로고
    • note
    • To facilitate comparison, we assigned the notation nnA to all the ternary complexes and transition states resulting from the replacement of the β-lactam 11 by the open NADH model 11A.
  • 70
    • 0009736224 scopus 로고
    • For similar observations on other NADH models, see
    • For similar observations on other NADH models, see: Marchelli, R.; Dradi, E.; Dossena, A.; Casnati, G. Tetrahedron 1982, 38, 2061-2067.
    • (1982) Tetrahedron , vol.38 , pp. 2061-2067
    • Marchelli, R.1    Dradi, E.2    Dossena, A.3    Casnati, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.