Convenient synthesis of 7′ and 6′-bromo-D-tryptophan and their derivatives by enzymatic optical resolution using D-aminoacylase

Tetrahedron

Volumn 58, Issue 39, 2002, Pages 7851-7861

  Konda Yamada, Yaeko ^a   Okada, Chiharu ^a   Yoshida, Kiminari ^a   Umeda, Yasuyuki ^a   Arima, Shiho ^a   Sato, Noriko ^a   Kai, Toshitsugu ^a   Takayanagi, Hiroaki ^a   Harigaya, Yoshihiro ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

7 and 6 bromo D tryptophan; D aminoacylase; Optical resolution; Synthesis

Indexed keywords

AMINOACYLASE; TRYPTOPHAN DERIVATIVE;

ACIDIFICATION; ARTICLE; ENANTIOSELECTIVITY; OPTICAL RESOLUTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037163333     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00909-2     Document Type: Article

References (23)

1. Schmiedeberg O. Arch. Exp. Pathol. Pharmakol. 13:1881;379-392.
2. Smorodinzev I.A. Z. Physiol. Chem. 124:1922;123.
3. Greenstein J.P., Wints M. Chemistry of the Amino Acids. Vol. 1:1961;Wiley, London, New York. pp 715-760, and references cited therein.
4. Birnbaum S.M., Levintow R., Kingsley B., Greenstein J.P. J. Biol. Chem. 194:1952;445-470.
5. Boger D.L., Keim H., Oberhauser B., Schhreiner E.P., Foster C.A. J. Am. Chem. Soc. 121:1999;6197-6205 Yokoyama Y., Osanai K., Mitsuhashi M., Kondou K., Murakami Y. Heterocycles. 55:(4):2001;653-659.
6. Boger D.L., Keim H., Oberhauser B., Schhreiner E.P., Foster C.A. J. Am. Chem. Soc. 121:1999;6197-6205 Yokoyama Y., Osanai K., Mitsuhashi M., Kondou K., Murakami Y. Heterocycles. 55:(4):2001;653-659.
7. Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 169:1952;1016 Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 181:1958;1225 Kameda Y., Toyoura E., Kimura Y., Matsui K. J. Pharm. Soc. Jpn. 78:1958;202.
8. Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 169:1952;1016 Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 181:1958;1225 Kameda Y., Toyoura E., Kimura Y., Matsui K. J. Pharm. Soc. Jpn. 78:1958;202.
9. Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 169:1952;1016 Kameda Y., Toyoura E., Kimura Y., Yamazoe H. Nature. 181:1958;1225 Kameda Y., Toyoura E., Kimura Y., Matsui K. J. Pharm. Soc. Jpn. 78:1958;202.
10. Sugie M., Suzuki H. Agric. Biol. Chem. 44:1980;1089-1095.
11. Fukagawa, Y.; Kubo, K.; Ishikura, T.; Kouno, K. J. Antibiot. 33 (6), 543-549.
12. Matsuzaki K., Ikeda H., Ogino T., Matsumoto A., Woodruff H.B., Tanaka H., Omura S. J. Antibiot. 47:1994;1173-1174 Gouda H., Matsuzaki K., Tanaka H., Hirono S., Omura S. J. Am. Chem. Soc. 118:1996;13087-13088.
13. Matsuzaki K., Ikeda H., Ogino T., Matsumoto A., Woodruff H.B., Tanaka H., Omura S. J. Antibiot. 47:1994;1173-1174 Gouda H., Matsuzaki K., Tanaka H., Hirono S., Omura S. J. Am. Chem. Soc. 118:1996;13087-13088.
14. Beugelmans R., Roussi G., Zamora E.G. Tetrahedron. 55:1999;5089-5112.
15. Nakamura K., Nishiyama S., Yamamura S. Terahedron Lett. 36:(47):1995;8621-8624.
16. Kai T., Kajimoto N., Konda Y., Harihaya Y., Takayanagi H. Tetrahedron Lett. 40:1999;6289-6292.
17. Bartoli G., Palmieri G., Chimiche D.S., Basco M., Dalpozzo R., Organia D.C. Tetrahedron Lett. 30:1989;2129-2132.
18. (a) Synder H.R., Macdonald J.A. J. Am. Chem. Soc. 77:1955;1257-1259
19. (b) Yokoyama Y., Hikawa H., Mitsuhashi M., Uyama A., Murakami M. Tetrahedron Lett. 40:1999;7803-7806.
20. Hangartner Y., Valentine D. Jr., Johnson K.K., Larscheid M.E., Pigott F., Scheidl F., Scott J.W., Sun R.C., Townsend J.M., Williams T.H. J. Org. Chem. 44:1979;3741-3747.
21. Allen M.C., Brundish D.E., Wade R. J. Chem. Soc., Perkin Trans. 1. 1980;1928-1932.
22. Chevallet P., Grrouste P., Malawska B., Martinez J. Tetrahedron Lett. 34:1993;7409-7412.
23. Moyer M.P., John F., Shiurba J.F., Rapoport H. J. Org. Chem. 51:1986;5106-5110.