Synthetic Studies on an Antitumor Antibiotic, Bleomycin. XII. Preparation of an L-2, 3-Diaminopropionic Acid Derivative as a Synthetic Intermediate
Three methods have been developed for the preparation of (S)-3-amino-2-tert-butoxycar-bonylaminopropionamide suitably protected for use in the total synthesis of bleomycin.
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| Published in | Chemical & pharmaceutical bulletin Vol. 33; no. 2; pp. 509 - 514 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
1985
公益社団法人日本薬学会 Maruzen |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 |
| DOI | 10.1248/cpb.33.509 |
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| Abstract | Three methods have been developed for the preparation of (S)-3-amino-2-tert-butoxycar-bonylaminopropionamide suitably protected for use in the total synthesis of bleomycin. |
|---|---|
| AbstractList | Three methods have been developed for the preparation of (S)-3-amino-2-tert-butoxycar-bonylaminopropionamide suitably protected for use in the total synthesis of bleomycin. |
| Author | OTSUKA, MASAMI KITTAKA, ATSUSHI OHNO, MASAJI YAMASHITA, HARUO KOBAYASHI, SUSUMU IIMORI, TAKAMASA |
| Author_FL | OTSUKA MASAMI KOBAYASHI SUSUMU IIMORI TAKAMASA YAMASHITA HARUO KITTAKA ATSUSHI OHNO MASAJI |
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| References | 10) L. Benoiton, Can. J. Chem., 46, 1549 (1968). 8) J. P. Greenstein and M. Winitz, "Chemistry of the Amino Acids," Vol. III, John Wiley-and Sons, Inc., New York, 1961, p. 2463. d) Part IV: M. Otsuka, M. Yoshida, S. Kobayashi, M. Ohno, Y. Umezawa, and H. Morishima, Tetrahedron Lett., 22, 2109 (1981 9) S. Takagi, H. Tsukatani, and K. Hayashi, Chem. Pharm. Bull., 7, 616 (1959). 13) H. Yamashita, T. Iimori, M. Otsuka, S. Kobayashi, and M. Ohno, Abstracts of Papers, 103rd Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, April 1983, p. 198. Hecht, Springer-Verlag, New York, 1979, p. 63 2) T. Takita, Y. Muraoka, T. Nakatani, A. Fujii, Y. Umezawa, H. Naganawa, and H. Umezawa, J. Antibiot., 26, 801 (1978). c) Part III: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 22, 671 (1981 g) Part VII: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Naganawa, H. Umezawa, T. Tsuchiya, T. Miyabe, S. Kageyama, S. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, M. Narita, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 23, 521 (1982 f) Part VI: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, S. Kobayashi, M. Ohno, T. Tsuchiya, T. Miyake, and S. Umezawa, Proceedings of the Seventh American Peptide Symposium, ed. by D. H. Rich and E. Gross, 1981, p. 29 k) Part XI: H. Umezawa, T. Takita, Y. Sugiura, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron, 40, 501 (1984). b) R. B. Sykes, C. M. Cimarusti, D. P. Bonner, K. Bush, D. M. Floyd, N. H. Georgopapadakou, W. H. Koster, W. C. Liu, W. L. Principe, M. L. Rathnum, W. A. Slusarchyk, W. H. Trejo, and J. J. Wells, Nature (London), 291, 498 (1981). 5) T. Kitagawa, T. Ozasa, and H. Taniyama, Yakugaku Zasshi, 89, 285 (1969). h) Part VIII: M. Narita, M. Otsuka, S. Kobayashi, M. Ohno, Y. Umezawa, H. Morishima, S. Saito, T. Takita, and H. Umezawa, Tetrahedron Lett., 23, 525 (1982 i) Part IX: S. Saito, Y. Umezawa, H. Morishima, T. Takita, H. Umezawa, M. Narita, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 23, 529 (1982 e) Part V: M. Otsuka, M. Yoshida, S. Kobayashi, M. Ohno, Y. Sugiura, T. Takita, and H. Umezawa, J. Am. Chem. Soc., 103, 6986 (1981 4) a) A. Imada, K. Kitano, K. Kintaka, M. Muroi, and M. Asai, Nature (London), 289, 590 (1981 6) a) P. Karrer and A. Schlosser, Helv. Chim. Acta, 6, 441 (1923 11) I. Photaki, J. Am. Chem. Soc., 85, 1123 (1963). 7) J. Rundiger, K. Poduska, and M. Zaoral, Collect. Czech. Chem. Commun., 25, 2022 (1960). b) F. Schneider, Justus Liebigs Ann. Chem., 529, 1 (1937). b) Part II: Y. Umezawa, H. Morishima, S. Saito, T. Takita, H. Umezawa, S. Kobayashi, M. Otsuka, M. Narita, and M. Ohno, J. Am. Chem. Soc., 102, 6630 (1980 1) a) Part I: Y. Umezawa, H. Morishima, T. Yoshioka, M. Otsuka, and M. Ohno, "Bleomycin," ed. by S. M. 12) O. Mitsunobu, Synthesis, 1981, 1. 3) M. Hashimoto, T. Konomi, and T. Kamiya, J. Am. Chem. Soc., 98, 3023 (1976). j) Part X: Y. Sugiura, T. Suzuki, M. Otsuka, S. Kobayashi, M. Ohno, T. Takita, and. H. Umezawa, J. Biol. Chem., 258, 1328 (1983 |
| References_xml | – reference: 13) H. Yamashita, T. Iimori, M. Otsuka, S. Kobayashi, and M. Ohno, Abstracts of Papers, 103rd Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, April 1983, p. 198. – reference: j) Part X: Y. Sugiura, T. Suzuki, M. Otsuka, S. Kobayashi, M. Ohno, T. Takita, and. H. Umezawa, J. Biol. Chem., 258, 1328 (1983); – reference: 6) a) P. Karrer and A. Schlosser, Helv. Chim. Acta, 6, 441 (1923); – reference: 2) T. Takita, Y. Muraoka, T. Nakatani, A. Fujii, Y. Umezawa, H. Naganawa, and H. Umezawa, J. Antibiot., 26, 801 (1978). – reference: d) Part IV: M. Otsuka, M. Yoshida, S. Kobayashi, M. Ohno, Y. Umezawa, and H. Morishima, Tetrahedron Lett., 22, 2109 (1981); – reference: b) R. B. Sykes, C. M. Cimarusti, D. P. Bonner, K. Bush, D. M. Floyd, N. H. Georgopapadakou, W. H. Koster, W. C. Liu, W. L. Principe, M. L. Rathnum, W. A. Slusarchyk, W. H. Trejo, and J. J. Wells, Nature (London), 291, 498 (1981). – reference: Hecht, Springer-Verlag, New York, 1979, p. 63; – reference: b) Part II: Y. Umezawa, H. Morishima, S. Saito, T. Takita, H. Umezawa, S. Kobayashi, M. Otsuka, M. Narita, and M. Ohno, J. Am. Chem. Soc., 102, 6630 (1980); – reference: c) Part III: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 22, 671 (1981); – reference: 9) S. Takagi, H. Tsukatani, and K. Hayashi, Chem. Pharm. Bull., 7, 616 (1959). – reference: f) Part VI: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, S. Kobayashi, M. Ohno, T. Tsuchiya, T. Miyake, and S. Umezawa, Proceedings of the Seventh American Peptide Symposium, ed. by D. H. Rich and E. Gross, 1981, p. 29; – reference: 8) J. P. Greenstein and M. Winitz, "Chemistry of the Amino Acids," Vol. III, John Wiley-and Sons, Inc., New York, 1961, p. 2463. – reference: i) Part IX: S. Saito, Y. Umezawa, H. Morishima, T. Takita, H. Umezawa, M. Narita, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 23, 529 (1982); – reference: g) Part VII: T. Takita, Y. Umezawa, S. Saito, H. Morishima, H. Naganawa, H. Umezawa, T. Tsuchiya, T. Miyabe, S. Kageyama, S. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, M. Narita, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 23, 521 (1982); – reference: 12) O. Mitsunobu, Synthesis, 1981, 1. – reference: 4) a) A. Imada, K. Kitano, K. Kintaka, M. Muroi, and M. Asai, Nature (London), 289, 590 (1981); – reference: 3) M. Hashimoto, T. Konomi, and T. Kamiya, J. Am. Chem. Soc., 98, 3023 (1976). – reference: 1) a) Part I: Y. Umezawa, H. Morishima, T. Yoshioka, M. Otsuka, and M. Ohno, "Bleomycin," ed. by S. M. – reference: 7) J. Rundiger, K. Poduska, and M. Zaoral, Collect. Czech. Chem. Commun., 25, 2022 (1960). – reference: b) F. Schneider, Justus Liebigs Ann. Chem., 529, 1 (1937). – reference: k) Part XI: H. Umezawa, T. Takita, Y. Sugiura, M. Otsuka, S. Kobayashi, and M. Ohno, Tetrahedron, 40, 501 (1984). – reference: 10) L. Benoiton, Can. J. Chem., 46, 1549 (1968). – reference: h) Part VIII: M. Narita, M. Otsuka, S. Kobayashi, M. Ohno, Y. Umezawa, H. Morishima, S. Saito, T. Takita, and H. Umezawa, Tetrahedron Lett., 23, 525 (1982); – reference: 11) I. Photaki, J. Am. Chem. Soc., 85, 1123 (1963). – reference: e) Part V: M. Otsuka, M. Yoshida, S. Kobayashi, M. Ohno, Y. Sugiura, T. Takita, and H. Umezawa, J. Am. Chem. Soc., 103, 6986 (1981); – reference: 5) T. Kitagawa, T. Ozasa, and H. Taniyama, Yakugaku Zasshi, 89, 285 (1969). |
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| SubjectTerms | (S)-3-amino-2-tert-butoxycarbonylaminopropionamide Alanine - analogs & derivatives Aliphatic compounds beta-Alanine - analogs & derivatives beta-Alanine - chemical synthesis bleomycin Bleomycin - chemical synthesis Chemical Phenomena Chemistry Exact sciences and technology Hofmann rearrangement L-2, 3-diaminopropionic acid L-asparagine L-serine Mitsunobu reaction Organic chemistry Preparations and properties |
| Title | Synthetic Studies on an Antitumor Antibiotic, Bleomycin. XII. Preparation of an L-2, 3-Diaminopropionic Acid Derivative as a Synthetic Intermediate |
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