Preparations of Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl] β-hydroxy α-amino acid derivatives

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 2, 1996, Pages 465-468

  Wakamiya, Tateaki ^a   Nishida, Takatoshi ^a   Togashi, Ryusaku ^a   Saruta, Kunio ^b   Yasuoka, Jun Ichi ^b   Kusumoto, Shoichi ^b  

^a KINKI UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; HYDROXYACID; PHOSPHOPEPTIDE; SERINE DERIVATIVE; THREONINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOMATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029865332     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.465     Document Type: Article

References (21)

1. A part of this work was presented in: a) K. Saruta, T. Wakamiya, J. Yasuoka, and S. Kusumoto, "the 67th National Meeting of the Chemical Society of Japan," Tokyo, March 1994, Abstr., No 2E16; b) T. Wakamiya, K. Saruta, Y. Yasuoka, and S. Kusumoto, Chem. Lett., 1994, 1099; c) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 23rd European Peptide Symposium," Braga, September 1994, Abstr., No P364; e) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 32nd Japanese Peptide Symposium," Fukuoka, October 1994, Abstr., No. O2, and published in "Peptide Chemistry 1994," ed by M. Ohno, Protein Research Foundation, Osaka (1995), p. 5.
2. A part of this work was presented in: a) K. Saruta, T. Wakamiya, J. Yasuoka, and S. Kusumoto, "the 67th National Meeting of the Chemical Society of Japan," Tokyo, March 1994, Abstr., No 2E16; b) T. Wakamiya, K. Saruta, Y. Yasuoka, and S. Kusumoto, Chem. Lett., 1994, 1099; c) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 23rd European Peptide Symposium," Braga, September 1994, Abstr., No P364; e) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 32nd Japanese Peptide Symposium," Fukuoka, October 1994, Abstr., No. O2, and published in "Peptide Chemistry 1994," ed by M. Ohno, Protein Research Foundation, Osaka (1995), p. 5.
3. A part of this work was presented in: a) K. Saruta, T. Wakamiya, J. Yasuoka, and S. Kusumoto, "the 67th National Meeting of the Chemical Society of Japan," Tokyo, March 1994, Abstr., No 2E16; b) T. Wakamiya, K. Saruta, Y. Yasuoka, and S. Kusumoto, Chem. Lett., 1994, 1099; c) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 23rd European Peptide Symposium," Braga, September 1994, Abstr., No P364; e) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 32nd Japanese Peptide Symposium," Fukuoka, October 1994, Abstr., No. O2, and published in "Peptide Chemistry 1994," ed by M. Ohno, Protein Research Foundation, Osaka (1995), p. 5.
4. A part of this work was presented in: a) K. Saruta, T. Wakamiya, J. Yasuoka, and S. Kusumoto, "the 67th National Meeting of the Chemical Society of Japan," Tokyo, March 1994, Abstr., No 2E16; b) T. Wakamiya, K. Saruta, Y. Yasuoka, and S. Kusumoto, Chem. Lett., 1994, 1099; c) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 23rd European Peptide Symposium," Braga, September 1994, Abstr., No P364; e) T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, "the 32nd Japanese Peptide Symposium," Fukuoka, October 1994, Abstr., No. O2, and published in "Peptide Chemistry 1994," ed by M. Ohno, Protein Research Foundation, Osaka (1995), p. 5.
5. T. Wakamiya, M. Kawahara, S. Kusumoto, S. Imajoh-Ohmi, and S. Kanegasaki, "Peptide Chemistry 1991," ed by A. Suzuki, Protein Research Foundation, Osaka (1992), p. 383.
6. T. Wakamiya, Chem. Express, 7, 577 (1992).
7. T. Wakamiya, K. Saruta, S. Kusumoto, K. Nakajima, K. Yoshizawa-Kumagaye, S. Imajoh-Ohmi, and S. Kanegasaki, Chem. Lett., 1993, 1401.
8. T. Wakamiya, K. Saruta, S. Kusumoto, S. Aimoto, K. Yoshizawa-Kumagaye, and K. Nakajima, "Peptide Chemistry 1993," ed by Y. Okada, Protein Research Foundation, Osaka (1994), p. 17.
9. K. Sato, K. Ishiguro, A. Omori, J. I. Kim, T. Uchida, K. Saruta, and T. Wakamiya, "Peptide Chemistry 1993," ed by Y. Okada, Protein Research Foundation, Osaka (1994), p. 109.
10. T. Wakamiya, K. Saruta, J. Yasuoka, and S. Kusumoto, Bull. Chem. Soc. Jpn., 68, 2699 (1995).
11. J. -M. Lacombe, F. Andriamanampisoa, and A. A. Pavia, Int. J. Pept. Protein Res., 36, 275 (1990).
12. This methodology is applicable to the synthesis of phosphotyrosine-containing peptides, since tyrosine is not β-hydroxy α-amino acid.
13. Abbreviations-AcOEt: ethyl acetate; Bzl: benzyl; Boc: t-butoxycarbonyl; mCPBA: m-chloroperbenzoic acid; DCHA: dicyclohexylamine; DMF: N,N-dimethylformamide; Fmoc: 9-fluorenylmethoxycarbonyl; i-Pr: isopropyl; Pac: phenacyl; Ser: serine; Thr: threonine; Tce: 2,2,2-trichloroethyl; TFA: trifluoro-acetic acid: THF: tetrahydrofuran.
14. R. B. King and P. M. Sundaram, J. Org. Chem., 49, 1784 (1984).
15. T. Shimidzu, K. Yamana, and S. Maikuma, Tetrahedron Lett., 25, 4237 (1984).
16. T. Tanaka, S. Tamatsukuri, and M. Ikehara, Tetrahedron Lett., 27, 199 (1986).
17. C. E. Dreef, C. J. J. Elie, P. Hoogerhout, G. A. van der Marel, and J. H. van Boom, Tetrahedron Lett., 29, 6513 (1988).
18. C. G. Fields and G. B. Fields, Int. J. Pept. Protein Res., 35, 161 (1990).
19. D. S. King, C. G. Fields, and G. B. Fields, Int. J. Pept. Protein Res., 36, 255 (1990).
20. J. D. Dittmer and R. L. Lester, J. Lipid Res., 5, 126 (1964).
21. 4 is recommended to suppress such salt formation.