Amino acids and peptides. XLIV. Synthesis of stereoisomeric pentapeptides of thiol proteinase inhibitor

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 8, 1996, Pages 1599-1602

  Iguchi, Shin ^a   Hirano, Kenichi ^a   Okamoto, Hiroshi ^a   Okamoto, Yoshiko ^b   Okada, Yoshio ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b DAIICHI UNIVERSITY OF PHARMACY   (Japan)

Author keywords

circular dichroism spectra; stereoisomeric pentapeptide; structure activity relationship; thiol proteinase inhibitor; TPI common sequence

Indexed keywords

CYSTEINE PROTEINASE INHIBITOR; DEXTRO AMINO ACID; PAPAIN;

ARTICLE; CIRCULAR DICHROISM; PEPTIDE SYNTHESIS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

EID: 0029761096     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1599     Document Type: Article

References (10)

1. Part XLIII: Okada Y., Mu Y., J. Chem. Soc., Perkia Trans. 1, "submitted."
2. The customary L indication for amino acid residues is omitted; only D isomers are indicated. Standard abbreviations for amino acids and their derivatives are those recommended by the IUPAC-IUB Commission on Biochemical Nomenclature: Biochemistry, 5, 3485 (1966); ibid., 6, 362 (1967); ibid., 11, 1726 (1972). Other abbreviations used are: Z, benzyloxycarbonyl: Suc, succinyl; iNoc, isonicotinyl; pNA, p-nitroanilide; OMe, methyl ester; ONp, p-nitrophenyl ester; DMF, N,N-dimethylformamide; THF, tetra-hydrofuran; AcOH, acetic acid; Bz Arg-βNA, N*-benzoyl-t>,L-Arg-2-naphthylamide; HATU, O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; NMM, N-methylmorpholine.
3. The customary L indication for amino acid residues is omitted; only D isomers are indicated. Standard abbreviations for amino acids and their derivatives are those recommended by the IUPAC-IUB Commission on Biochemical Nomenclature: Biochemistry, 5, 3485 (1966); ibid., 6, 362 (1967); ibid., 11, 1726 (1972). Other abbreviations used are: Z, benzyloxycarbonyl: Suc, succinyl; iNoc, isonicotinyl; pNA, p-nitroanilide; OMe, methyl ester; ONp, p-nitrophenyl ester; DMF, N,N-dimethylformamide; THF, tetra-hydrofuran; AcOH, acetic acid; Bz Arg-βNA, N*-benzoyl-t>,L-Arg-2-naphthylamide; HATU, O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; NMM, N-methylmorpholine.
4. The customary L indication for amino acid residues is omitted; only D isomers are indicated. Standard abbreviations for amino acids and their derivatives are those recommended by the IUPAC-IUB Commission on Biochemical Nomenclature: Biochemistry, 5, 3485 (1966); ibid., 6, 362 (1967); ibid., 11, 1726 (1972). Other abbreviations used are: Z, benzyloxycarbonyl: Suc, succinyl; iNoc, isonicotinyl; pNA, p-nitroanilide; OMe, methyl ester; ONp, p-nitrophenyl ester; DMF, N,N-dimethylformamide; THF, tetra-hydrofuran; AcOH, acetic acid; Bz Arg-βNA, N*-benzoyl-t>,L-Arg-2-naphthylamide; HATU, O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; NMM, N-methylmorpholine.
5. Okada Y., Teno N., Tuboi S., Nakabayashi K., Itoh N., Okamoto H., Nishi N., Chem. Pharm. Bull., 36, 1982 (1988).
6. Okada Y., Tsuda Y., Mu Y., Hirano K., Okamoto H., Okamoto Y., Kakegawa H., Matsumoto H., Sato T., Chem. Pharm. Bull., 43, 96 (1995).
7. Yamamoto A., Tomoo K., Doi M., Ohishi H., Inoue M., Ishida T., Yamamoto D., Tuboi S., Okamoto H., Okada Y., Biochemistry, 31, 11305 (1992).
8. Okada Y., Teno N., Itoh N., Okamoto H., Chem. Pharm. Bull, 33, 5149 (1985).
9. Carpino L. A., J. Am. Chem. Soc., 115, 4397 (1993); Carpino L. A., El-Faham A , Albericio F., Tetrahedron Lett., 35, 2279 (1994).
10. Carpino L. A., J. Am. Chem. Soc., 115, 4397 (1993); Carpino L. A., El-Faham A , Albericio F., Tetrahedron Lett., 35, 2279 (1994).