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Nucleosides, Nucleotides & Nucleic Acids Volume 20, 2001 - Issue 4-7
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Original Articles

MECHANISM OF INACTIVATION OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE BY 5′-DEOXY-5′-S-ALLENYLTHIOADENOSINE AND 5′-DEOXY-5′-S-PROPYNYLTHIOADENOSINE

G. Guillerm Université de Reims, Laboratoire des Réactions Sélectives et Applications - UMR 6519, BP 1039, Reims, Cédex 2, 51687, France
,
D. Guillerm Université de Reims, Laboratoire des Réactions Sélectives et Applications - UMR 6519, BP 1039, Reims, Cédex 2, 51687, France
&
C. Witkowski-Vandenplas Université de Reims, Laboratoire des Réactions Sélectives et Applications - UMR 6519, BP 1039, Reims, Cédex 2, 51687, France
Pages 685-688 | Published online: 07 Feb 2007

REFERENCES

  • Liu , S. , Wolfe , M. S. and Borchardt , R. T. 1992 . Antiviral Research , 19 : 247 – 265 .
  • Yuan , C. S. , Liu , S. , Wnuk , S. F. , Robins , M. J. and Borchardt , R. T. 1996 . Advances in Antiviral Drug Design Edited by: De Clercq , E. Vol. 2 , 41 – 88 . Greenwich : JAI Press .
  • Parry , R. J , Muscate , A. and Askonas , L. J. 1991 . Biochemistry , 30 : 9988 – 9997 .
  • Wnuk , S. F. , Mao , Y. , Yuan , C. S. , Borchardt , R. T. , Andrei , G. , Balzarini , J. , De Clercq , E. and Robins , M. J. 1998 . J. Med. Chem. , 41 : 3078 – 3083 .
  • Yuan , C. S. , Wnuk , S. F. and Robins , M. J. J. 1998 . Biol. Chem. , 273 : 18191 – 18197 .
  • Muzard , M. , Vandenplas , C. , Guillerm , D. and Guillerm , G. 1998 . J. Enz. Inh. , 13 : 443 – 456 .
  • Houston , M. E. Jr , Vander Jagt , D. L. and Honek , J. F. 1991 . Bioorg. Med. Chem. Lett. , 11 : 623 – 628 .
  • 4 : mp 87–89°C - HRMS (DCI/NH3) 322.084 (MH)+, calc. 321.299 -[α]20 D −20.5° (c 0,23; CHCl3/MeOH: 4/1). I.R.(KBr) 2170, 3281 cm−1 − 1H NMR, CDCl3, ϵ CD3OD δ (ppm), J(Hz): 2.27 (t, 1H, C≡CH, J 2.67); 3.01 (dd, 1H, H5′α, J 14.11, 6.1); 3.12 (dd, 1H, H5′β, J 14 .11, 4.57); 3.28 (d, 2H, CH 2C≡C, 2.67); 4.21 (m, 1H, H-4′); 4.29 (dd, 1H, H-3′, J 5.34, 5,72); 4.46 (dd, 1H, H-2′, J 5.34, 3.81); 5.81 (d, 1H, H-1′, J 3.81); 8.09 and 8.21 (2 s, 2H, H-2 and H-8) -13C NMR, CDCl3 ϵ CD3OD, δ (ppm) : 20.0 (CH2C≡C); 33.3 (C-5′); 71.6(C≡CH); 72.3 (C-4′); 74.2 (C-3′); 80.0 (C≡CH); 83.9 (C-2′); 89.6 (C-1′); 120.0 (C-6); 139.3 and 152.8 (C-2 and C-8); 149.1 and 155.9 (C-4 and C-5)
  • 1 mp 90–92°C - HRMS (DCI/NH3) 322.098 (MH)+, calc.321.299 -[α]20 D −18° (c 0.18; CHCl3/MeOH: 4/1) - I.R.(KBr) 1944 cm−1 (weak) - 1H NMR, CDCl3, ϵ CD3OD δ (ppm), J(Hz): 2.93 (dd, 1H, H-5′α, J 14.5, 4.96); 3.05 (dd, 1H, H-5′β, J 14.5, 4.96); 4.21 (m, 1H, H-4′); 4.22 (dd, 1H, H-3′, J 6.1, 4.95); 4.49 (dd, 1H, H-2′, J 4.95, 4,2); 4.94 (d, 2H, CH2˭C˭CHS, J 6,48); 5.70 (dd, 1H, CH2˭C˭CHS, J 6.48); 5.86 (d, 1H, H-1′, J 4.2); 8.05 and 8.15 (2 s, 2H, H-2 and H-8) - 13C NMR, CDCl3 ϵ CD3OD, δ (ppm) : 34.2 (C-5′); 72.1 (C-4′); 74.2 (C-3′); 81.0 (CH2˭C˭CHS); 83.0 (C-2′); 87.0 (CH2˭C˭CHS); 89.3 (C-1′); 119.4 (C-6); 139.1 and 152.2 (C-2 and C-8); 148.7 and 155.3 (C-4 and C-5); 205.6 (CH2˭C˭CHS)
  • 2 mp 95–97°C - HRMS (DCI/NH3) 322.306 (MH)+, calc.321.299 - [α]20 D +22.5 (c 0.020; CHCl3/MeOH: 4/1) - 1H NMR, CDCl3, ϵ CD3OD δ (ppm), J (Hz): 1.87 (s, 3H, C≡CCH 3); 3.02 (dd, 1H, H-5′α J 13,72, 6,5); 3.13 (dd, 1H, H-5′β, J 13.72, 6,1); 4.31 (m, 1H, H-4′); 4.32 (dd, 1H, H-3′, J 2,27, 5,2) 4.39 (dd, 1H, H-2′, J 5.2, 3,6); 6.04 (d, 1H, H-1′, J 3.6); 8.19 and 8.29 (2 s, 2H, H-2 and H-8) - 13C NMR, CDCl3, ϵ CD3OD, δ (ppm): 4.4 (C≡CCH3,); 39.2 (C-5′); 68 (C≡CCH3); 73.8 (C-4′); 74.8 (C-3′); 84.8 (C-2′); 89.0 (C≡CCH3); 90 (C-1′); 119.4 (C-6); 141.2 and 153.8 (C-2 and C-8); 150 and 157.3 (C-4 and C-5)
  • Coulter-Karis , D. E. and Hershfield , M. S. 1989 . Ann. Hum. Genet. , 53 : 169 – 175 .
  • Yuan , C.-S. , Yeh , J. , Liu , S. and Borchardt , R. 1993 . J. Biol. Chem. , 268 : 17030 – 17037 .
  • Della Ragione , F. and Pegg , A. E. 1983 . Biochem. J. , : 210 – 429 .
  • Kitz , K. and Wilson , I. B. 1962 . J. Biol. Chem. , 237 : 3245 – 3249 .

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