Organic Letters
Letter
(5) (a) Wiegand, M.; Lindhorst, T. K. Eur. J. Org. Chem. 2006, 21,
4841. (b) Kuboe, S.; Yoda, M.; Ogata, A.; Kitade, Y.; Tomari, Y.;
Ueno, Y. Chem. Commun. 2010, 46, 7367. (c) Ismaili, H.; Lee, S.;
Workentin, M. S. Langmuir 2010, 26, 14958. (d) Nakamoto, K.; Ueno,
Y. J. Org. Chem. 2014, 79, 2463.
(6) (a) Bentz, E. L.; Gibson, H.; Hudson, C.; Moloney, M. G.;
Seldon, D. A.; Wearmouth, E. S. Synlett 2006, 2, 247. (b) Lawrence, E.
J.; Wildgoose, G. G.; Aldous, L.; Wu, Y. A.; Warner, J. H.; Compton,
R. G.; McNaughter, P. D. Chem. Mater. 2011, 23, 3740. (c) Sanderson,
J. M.; Findlay, J. B. C.; Fishwick, C. W. G. Tetrahedron 2005, 61,
11244. (d) Baldwin, J. E.; Jesudason, C. D.; Moloney, M. G.; Morgan,
deuterated L-(4-Tmd)Phe 17 from deuterated L-Phe 16. HPLC
spectra indicated that all of the (Tmd)Phe derivatives (9, 11,
13, 15, and 17) retained their optical purity (Figure S3,
Supporting Information). The photoreactive properties of the
L-(Tmd)Phe derivatives (9, 13, and 17) were further
investigated in the presence of CH3OH and CD3OD under
UV irradiation (Figure S4, Supporting Information). The half-
lives (t1/2) were calculated as 1.3, 0.6, and 1.3 min for 9, 13, and
17, respectively, indicating their effective photoreactivity. Then,
the reaction mixtures were subjected to MS analysis for
investigation of the photoreaction products (Figure S5,
Supporting Information).
D. R.; Pratt, A. J. Tetrahedron 1991, 47, 5603. (e) Fernan
́
dez-Gacio, A.;
Mourino, A. Eur. J. Org. Chem. 2002, 15, 2529. (f) Hatanaka, Y.;
̃
Nakayama, H.; Kanaoka, Y. Heterocycles 1993, 35, 997. (g) Halbfinger,
In conclusion, we developed a novel approach to synthesize
TPD derivatives from the corresponding tosyloximes in a one-
́
E.; Gorochesky, K.; Levesque, S. A.; Beaudoin, A. R.; Sheihet, L.;
Margel, S.; Fischer, B. Org. Biomol. Chem. 2003, 1, 2821. (h) Murai, Y.;
Masuda, K.; Ogasawara, Y.; Wang, L.; Hashidoko, Y.; Hatanaka, Y.;
Iwata, S.; Kobayashi, T.; Hashimoto, M. Eur. J. Org. Chem. 2013, 12,
2428.
−
pot reaction. NH2 species generated from liquid NH3 or
lithium amide contribute to the formation of TPD derivatives.
These one-pot methods will significantly shorten the synthetic
route of TPD derivatives in photoaffinity labeling. To
conveniently prepare optically pure (Tmd)Phe derivatives,
these one-pot methods were applied. The result indicated that
liquid NH3 at 80 °C was feasible while reaction with lithium
amide in liquid NH3 led to the racemization of phenylalanine.
(7) (a) Ploug, M.; Østergaard, S.; Hansen, L. B. L.; Holm, A.; Danø,
K. Biochemistry 1998, 37, 3612. (b) Nakashima, H.; Hashimoto, M.;
Sadakane, Y.; Tomohiro, T.; Hatanaka, Y. J. Am. Chem. Soc. 2006, 128,
15092. (c) Fillion, D.; Deraet, M.; Holleran, B. J.; Escher, E. J. Med.
̈
Chem. 2006, 49, 2200. (d) High, S.; Martoglio, B.; Gorlich, D.;
Andersen, S. S. L.; Ashford, A. J.; Giner, A.; Hartmann, E.; Prehn, S.;
Rapoport, T. A.; Dobberstein, B.; Brunner, J. J. Biol. Chem. 1993, 268,
26745. (e) Tippmann, E. M.; Liu, W. S.; Summerer, D.; Mack, A. V.;
Schultz, P. G. ChemBioChem 2007, 8, 2210. (f) Baldini, G.; Martoglio,
B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27,
7951.
ASSOCIATED CONTENT
■
S
* Supporting Information
General information, experimental procedures, characterization,
and NMR, HPLC, UV, and mass spectra of corresponding
products. This material is available free of charge via the
(8) (a) Nassal, M. J. Am. Chem. Soc. 1984, 106, 7540. (b) Shih, L. B.;
Bayley, H. Anal. Biochem. 1985, 144, 132.
(9) Masuda, K.; Koizumi, A.; Misaka, T.; Hatanaka, Y.; Abe, K.;
Tanaka, T.; Ishiguro, M.; Hashimoto, M. Bioorg. Med. Chem. Lett.
2010, 20, 1081.
(10) (a) Fishwick, C. W. G.; Sanderson, J. M.; Findlay, J. B. C.
Tetrahedron Lett. 1994, 35, 4611. (b) Hashimoto, M.; Hatanaka, Y.;
Sadakane, Y.; Nabeta, K. Bioorg. Med. Chem. Lett. 2002, 12, 2507.
(11) Fernelius, W. C.; Bowman, G. B. Chem. Rev. 1940, 26, 3.
(12) Coulter, L. V.; Sinclair, J. R.; Cole, A. G.; Roper, G. C. J. Am.
Chem. Soc. 1959, 81, 2986.
(13) Bergstrom, F. W.; Fernelius, W. C. Chem. Rev. 1933, 12, 43.
(14) (a) Hatanaka, Y.; Hashimoto, M.; Nakayama, H.; Kanaoka, Y.
Chem. Pharm. Bull. 1994, 42, 826. (b) Hatanaka, Y.; Hashimoto, M.;
Kurihara, H.; Nakayama, H.; Kanaoka, Y. J. Org. Chem. 1994, 59, 383.
(15) Smith, R. A. G.; Knowles, J. R. J. Chem. Soc., Perkin Trans. 2
1975, 7, 686.
AUTHOR INFORMATION
■
Corresponding Author
Present Address
∥(Y.M.) Faculty of Advanced Life Science, Frontier Research
Center for Post-Genome Science and Technology, Hokkaido
University, Kita 21, Nishi 11, Kita-ku, Sapporo 001-0021, Japan.
Notes
The authors declare no competing financial interest.
(16) Ruff, O.; Geisel, E. Chem. Ber. 1906, 39, 842.
ACKNOWLEDGMENTS
■
(17) (a) Sinz, A. Angew. Chem., Int. Ed. 2007, 46, 660. (b) Song, Z.
Q.; Huang, W. G.; Zhang, Q. S. Chem. Commun. 2012, 48, 3339.
(18) Murai, Y.; Wang, L.; Masuda, K.; Sakihama, Y.; Hashidoko, Y.;
Hatanaka, Y.; Hashimoto, M. Eur. J. Org. Chem. 2013, 23, 5111.
(19) Wang, L.; Murai, Y.; Yoshida, T.; Okamoto, M.; Masuda, K.;
Sakihama, Y.; Hashidoko, Y.; Hatanaka, Y.; Hashimoto, M. Biosci.
Biotechnol. Biochem. 2014, 78, 1129.
M.H. thanks the Suhara Memorial Foundation for financial
support. Part of this work was performed under the
Cooperative Research Program of “Network Joint Research
Center for Materials and Devices”.
REFERENCES
■
(1) Brunner, J.; Senn, H.; Richards, F. M. J. Biol. Chem. 1980, 255,
3313.
(2) (a) Converse, C. A.; Richards, F. F. Biochemistry 1969, 8, 4431.
(b) Fleet, G. W. J.; Porter, R. R.; Knowles, J. R. Nature 1969, 224, 511.
(c) Ruoho, A. E.; Kiefer, H.; Roeder, P. E.; Singer, S. J. Proc. Natl.
Acad. Sci. U.S.A. 1973, 70, 2567.
(3) (a) Das, J. Chem. Rev. 2011, 111, 4405. (b) Smith, R. A. G.;
Knowles, J. R. J. Am. Chem. Soc. 1973, 95, 5072. (c) Hatanaka, Y.;
Yoshida, E.; Nakayama, H.; Kanaoka, Y. Bioorg. Chem. 1989, 17, 482.
(d) Hiramatsu, T.; Guo, Y.; Hosoya, T. Org. Biomol. Chem. 2007, 5,
2916. (e) Qiu, Z. H.; Lu, L. H.; Jian, X.; He, C. J. Am. Chem. Soc. 2008,
130, 14398. (f) Song, Z. Q.; Zhang, Q. S. Org. Lett. 2009, 11, 4882.
(4) Galardy, R. E.; Craig, L. C.; Jamieson, J. D.; Printz, M. P. J. Biol.
Chem. 1974, 249, 3510.
619
Org. Lett. 2015, 17, 616−619