Highly nuclease-resistant phosphodiester-type oligodeoxynucleotides containing 4'α-C-aminoalkylthymidines form thermally stable duplexes with DNA and RNA. A candidate for potent antisense molecules

Journal of the American Chemical Society

Volumn 122, Issue 11, 2000, Pages 2422-2432

  Kanazaki, Makiko ^a   Ueno, Yoshihito ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGODEOXYNUCLEOTIDE; DNA; NUCLEOSIDE; OLIGODEOXYNUCLEOTIDE DERIVATIVE; PHOSPHODIESTERASE; RIBONUCLEASE; RNA; SILANE DERIVATIVE; SNAKE VENOM; THYMIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; CONFORMATION; CONTROLLED STUDY; CYCLIZATION; HUMAN; HUMAN CELL; HYDROLYSIS; NONHUMAN; OXIDATION; REACTION ANALYSIS; SYNTHESIS; THERMOSTABILITY;

EID: 0034701268     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9934706     Document Type: Article

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22. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
23. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
24. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
25. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
26. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
27. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
28. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
29. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
30. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
31. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
32. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
33. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
34. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
35. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
36. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
37. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
38. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
39. Examples of ODNs carrying amines: (a) Tung, C.-H.; Breslauer, K. J.; Stein, S. Nucleic Acids Res. 1993, 21, 5489-5494. (b) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Bioorg. Med. Chem. Lett. 1994, 4, 1733-1738. (c) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Biochem. Biophys. Res. Commun. 1994, 205, 1665-1670. (d) Barawkar, D. A.; Rajeev, K. G.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res. 1996, 24, 1229-1237. (e) Schmid, N.; Behr, J.-P. Tetrahedron Lett. 1995, 36, 1447-1450. (f) Sund, C.; Puri, N.; Chattopadhyaya, J. Tetrahedron 1996, 52, 12275-12290. (g) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Org. Chem. 1993, 58, 4194-4195. (h) Hashimoto, H.; Nelson, M. G.; Switzer, C. J. Am. Chem. Soc. 1993, 115, 7128-7134. (i) Ozaki, H.; Nakamura, A.; Arai, M.; Endo, M.; Sawai, H. Bull. Chem. Soc. Jpn. 1995, 68, 1981-1987. (j) Shinozuka, K.; Umeda, A.; Aoki, T.; Sawai, H. Nucleosides Nucleotides 1998, 17, 291-300. (k) Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R.; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109. (l) Cuenoud, B.; Casset, F.; Hüsken, D.; Natt, F.; Wolf, R. M.; Altmann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1288-1291. (m) Dan, A.; Yoshimura, Y.; Ono, A.; Matsuda, A. Bioorg. Med. Chem. Lett. 1993, 3, 615-618. (n) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499-508. (o) Ono, A.; Haginoya, N.; Kiyokawa, M.; Minakawa, N.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 361-366. (p) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280. (q) Nomura, Y.; Ueno, Y.; Matsuda, A. Nucleic Acids Res. 1997, 25, 2784-2791. (r) Ueno, Y.; Kumagai, I.; Haginoya, N.; Matsuda, A. Nucleic Acids Res. 1997, 25, 3777-3782. (s) Ueno, Y.; Mikawa, M.; Matsuda, A. Bioconjugate Chem. 1998, 9, 33-39.
40. Wang, G.; Seifert, W. F. Tetrahedron Lett. 1996, 37, 6515-6518.
41. Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667.
42. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
43. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
44. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
45. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
46. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
47. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
48. Although several approaches to the introduction of carbon substituents at the 4′-position of nucleosides have been reported, these methods were not stereoselective and the type of carbon substituents introduced was limited: (a) Secrist, J. A., III; Winter, W. J. A., Jr. J. Am. Chem. Soc. 1978, 100, 2554-2556. (b) Youssefyeh, R. D.; Verheyden, P. H.; Moffat, J. G. J. Org. Chem. 1979, 44, 1301-1309. (c) Haraguch, K.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 227-230. (d) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Saito, S.; Miyasaka, T. Tetrahedron Lett. 1992, 33, 2841-2844. (e) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854-5855. (f) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1996, 61, 851-858. (g) Marx, A.; Erdmann, P.; Senn, M.; Komer, S.; Jungo, T.; Petretta, M.; Imwinkelried, P.; Dussy, A.; Kulicke, K. J.; Macko, L.; Zehnder, M.; Giese, B. Helv. Chim. Acta 1996, 79, 1980-1994.
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