References
1
Gryaznov SM.
Skórski T.
Cucco C.
Nieborowska-Skórska M.
Chin CY.
Lloyd D.
Chen J.-K.
Koziólkiewicz M.
Calabretta B.
Nucleic Acids Res.
1996,
24:
1508
2
Riordan ML.
Martin JC.
Nature (London)
1991,
350:
442
3
Gryaznov SM.
Lloyd DH.
Chen J.-K.
Schultz RG.
DeDionisio LA.
Ratmeyer L.
Wilson WD.
Proc. Natl. Acad. Sci. U.S.A.
1995,
92:
5798
4
Giovannangeli C.
Diviacco S.
Labrousse V.
Gryaznov S.
Charneau P.
Helene C.
Proc. Natl. Acad. Sci. U.S.A.
1997,
94:
79
5
Gryaznov SM.
Letsinger RL.
Nucleic Acids Res.
1992,
20:
3403
6
Rigl CT.
Lloyd DH.
Tsou DS.
Gryaznov SM.
Wilson WD.
Biochemistry
1997,
36:
650
7
Escude C.
Giovannangeli C.
Sun JS.
Lloyd DH.
Chen JK.
Gryaznov SM.
Garestier T.
Helene C.
Proc. Natl. Acad. Sci. U.S.A.
1996,
93:
4365
8
Mungall WS.
Greene GL.
Heavner GA.
Letsinger RL.
J. Org. Chem.
1975,
40:
1659
9
Maag H.
Schmidt B.
Rose SJ.
Tetrahedron Lett.
1994,
35:
6449
10
Chen J.-K.
Schultz RG.
Lloyd DH.
Gryaznov SM.
Nucleic Acids Res.
1995,
23:
2661
11
Gryaznov S.
Chen J.-K.
J. Am. Chem. Soc.
1994,
116:
3143
12
Chen J.-K.
Schultz RG.
Lloyd DH.
Gryaznov SM.
Nucleic Acids Res.
1995,
23:
2661
13
Schultz RG.
Gryaznov SM.
Nucleic Acids Res.
1996,
24:
2966
14
Uznanski B.
Grajkowski A.
Krzyzanowska B.
Kazmierkowska A.
Stec WJ.
Wieczorek MW.
Blaszczyk J.
J. Am. Chem. Soc.
1992,
114:
10197
15
Baraniak J.
Korczyñski D.
Stec WJ.
J. Org. Chem.
1999,
64:
4533
16
Garegg PJ.
Lindh I.
Regberg T.
Stawinski J.
Strömberg R.
Henrichson C.
Tetrahedron Lett.
1986,
27:
4051
17
Garegg PJ.
Lindh I.
Regberg T.
Stawinski J.
Strömberg R.
Henrichson C.
Tetrahedron Lett.
1986,
27:
4055
18
Froehler BC.
Matteucci MD.
Tetrahedron Lett.
1986,
27:
469
19
Froehler BC.
Ng PG.
Matteucci MD.
Nucleic Acids Res.
1986,
14:
5399
20
Stawinski J.
Kraszewski A.
Acc. Chem. Res.
2002,
35:
952
21
Kers I.
Stawinski J.
Tetrahedron Lett.
1998,
39:
1219
22
Kers I.
Stawinski J.
Tetrahedron
1999,
55:
11579
23 Spectral data for the representative products 6b and 8b.
Compound 6b: 31P NMR (121.5 MHz, DMSO-d
6): δ = 10.37, 10.26 ppm. 1H NMR (300 MHz, DMSO-d
6): δ = 1.76 (s, 3 H, 5-CH3 of 3′-amino-3′-deoxythymidine), 1.78 (s, 3 H, 5-CH3 of 3′-deoxythymidine), 2.11-2.17 (m, 5 H, 2′-H of 3′-amino-3′-deoxythymidine and 3′-deoxythymidine and 4′-H of 3′-amino-3′-deoxythymidine), 3.50-3.65 (m, 2 H, 3′-H of 3′-amino-3′-deoxythymidine and 3′-H of 3′-deoxythymidine), 3.65-3.93 (m, 2 H, 5′-H of 3′-amino-3′-deoxythymidine), 4.01 (m, 1 H, 4′-H of 3′-deoxythymidine), 4.01-4.11 (m, 2 H, 5′-H of 3′-deoxythymidine), 4.21-4.30 (m, 1 H, 3′-NH of 3′-amino-3′-deoxythymidine), 4.39-4.47 (m, 2 H, OCH
2-CH=CH2), 5.17-5.35 (m, 2 H, OCH2-CH=CH
2), 5.88-6.00 (m, 1 H, OCH2-CH=CH2), 6.12 (t, 1 H, 3
J = 6.18 Hz, 1′-H of 3′-amino-3′-deoxythymidine), 6.19 (t, 1 H, 3
J = 6.87 Hz, 1′-H of 3′-deoxythymidine), 7.52 (s, 1 H, 6-H of 3′-amino-3′-deoxythymidine), 7.73 (s, 1 H, 6-H of 3′-deoxythymidine), 11.29 (s, 1 H, 3-H of 3′-amino-3′-deoxythymidine), 11.32 (s, 1 H, 3-H of 3′-deoxythymidine) ppm. 13C NMR (75 MHz, DMSO-d
6): δ = 12.11, 12.26, 60.39, 65.58, 65.97, 66.05, 70.21, 70.30, 83.24, 83.88, 84.69, 85.80, 109.21, 109.83, 117.04, 133.53, 133.62, 135.81, 136.18, 150.35, 150.42, 163.70, 163.76 ppm. ESI-MS: m/z = 586.4 [M + H]+, 608.2 [M + Na]+.
Compound 8b: 31P NMR (121.5 MHz, DMSO-d
6): δ = 10.08, 10.30 ppm. 1H NMR (300 MHz, DMSO-d
6): δ = 1.76 (s, 3 H, 5-CH3 of 3′-amino-3′-deoxythymidine), 1.78 (s, 6 H, 5-CH3 of 3′-deoxythymidine and 3′-amino-3′-deoxythymidine), 1.99-2.35 (m, 6 H, 6 × H-2′), 3.54-3.86 (m, 5 H, H-4′ of 3′-deoxythymidine and 2 × H-5′), 3.87-4.33 (m, 8 H, 2 × H-4′, 4 × H-5′ and 2 × H-3′ of 3′-amino-3′-deoxythymidine), 4.33-4.50 (m, 3 H, 2 OCH
2-CH=CH2 and H-3′ of 3′-deoxythymidine), 5.10-5.38 (m, 4 H, 2 OCH2-CH=CH
2), 5.83-6.02 (m, 2 H, 2 OCH2-CH=CH2), 6.04-6.26 (m, 3 H, H-1′), 7.54 (s, 2 H, H-6 of 3′-deoxythymidine and 3′-amino-3′-deoxythymidine), 7.74 (s, 1 H, H-6 of 3′-amino-3′-deoxythymidine), 11.23-11.36 (m, 3 H, 3 × H of NH-3) ppm. 13C NMR (75 MHz, DMSO-d
6): δ = 12.60, 12.73, 50.82, 51.22, 60.76, 65.61, 65.76, 66.21, 66.51, 66.57, 66.74, 66.80, 70.59, 70.61, 79.75, 83.72, 83.97, 84.40, 85.03, 85.10, 86.35, 86.49, 109.72, 110.25, 110.34, 117.57, 117.74, 133.90, 133.97, 136.30, 136.72, 150.75, 150.84, 164.18 ppm. ESI-MS: m/z = 951.9 [M + Na]+.