Solid phase-mediated cyclization of head-to-tail peptides: Problems associated with side chain anchoring

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4229-4232

  Valero, Mari Luz ^a   Giralt, Ernest ^a   Andreu, David ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE;

ARTICLE; CYCLIZATION; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; PROTEIN ISOLATION; PROTEIN PURIFICATION; SOLID PHASE EXTRACTION;

EID: 0029992878     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00803-9     Document Type: Article

References (23)

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2. For reviews, see, inter alia: Blout, E.R. Biopolymers 1981, 20, 1901-1912; Ovchinnikov, Y.A.; Ivanov, V.T. In The Proteins. Neurath, H.; Hill, R.L. Ed.; Academic Press: New York. 1982, pp. 307-642; Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523; Hruby, V.J., Al-Obeidi, F., Kazmierski, W. Biochem. J. 1990, 268, 249-262; Rizo, J.; Gierasch, L.M. Annu. Rev. Biochem. 1992, 61, 387-418.
3. For reviews, see, inter alia: Blout, E.R. Biopolymers 1981, 20, 1901-1912; Ovchinnikov, Y.A.; Ivanov, V.T. In The Proteins. Neurath, H.; Hill, R.L. Ed.; Academic Press: New York. 1982, pp. 307-642; Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523; Hruby, V.J., Al-Obeidi, F., Kazmierski, W. Biochem. J. 1990, 268, 249-262; Rizo, J.; Gierasch, L.M. Annu. Rev. Biochem. 1992, 61, 387-418.
4. For reviews, see, inter alia: Blout, E.R. Biopolymers 1981, 20, 1901-1912; Ovchinnikov, Y.A.; Ivanov, V.T. In The Proteins. Neurath, H.; Hill, R.L. Ed.; Academic Press: New York. 1982, pp. 307-642; Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523; Hruby, V.J., Al-Obeidi, F., Kazmierski, W. Biochem. J. 1990, 268, 249-262; Rizo, J.; Gierasch, L.M. Annu. Rev. Biochem. 1992, 61, 387-418.
5. For reviews, see, inter alia: Blout, E.R. Biopolymers 1981, 20, 1901-1912; Ovchinnikov, Y.A.; Ivanov, V.T. In The Proteins. Neurath, H.; Hill, R.L. Ed.; Academic Press: New York. 1982, pp. 307-642; Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523; Hruby, V.J., Al-Obeidi, F., Kazmierski, W. Biochem. J. 1990, 268, 249-262; Rizo, J.; Gierasch, L.M. Annu. Rev. Biochem. 1992, 61, 387-418.
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7. Abbreviations used in this paper for amino acids and peptides follow the rules of the IUPAC-IUB Comission of Biochemical Nomenclature in Eur. J. Biochem., 1984, 138, 9-37 and J. Biol. Chem., 1989, 264, 633-673. The following additional abbreviations are used: AAA, amino acid analysis; All, allyl; Boc, tert-butoxycarbonyl; BOP, benzotriazole-1-yl-oxy-tris-(dimethylamino)phosphonium hexafluorophosphate; Bzl, benzyl; CI, chemical ionization; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCC, dicyclohexylcarbodiimide; DCM, dichloromethane; DIEA, N,N-diisopropylethylamine; DIPCDI, 1,3-diisopropylcarbodiimide; DMAP, 4-dimethylaminopyridine; DMF, dimethylformamide; Dnp, 2,4-dinitrophenyl; Fm, 9-fluorenylmethyl; Fmoc, 9-fluorenylmethyloxycarbonyl; GC-MS, gas chromatography-mass spectrometry; HOBt, 1-hydroxybenzotriazole; HPLC, high performance liquid chromatography; IR, infrared spectroscopy; MALDI-TOF, matrix-assisted laser desorption ionization/time-of-flight, MBHA, p-methylbenzhydrylamine; NMR, nuclear magnetic resonance, PyBOP, benzotriazole-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate; Su, succinimidyl; TBTU, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; TFA, trifluoroacetic acid; Tos, p-toluenesulfonyl. The amino acid symbols used denote the L configuration.
8. Abbreviations used in this paper for amino acids and peptides follow the rules of the IUPAC-IUB Comission of Biochemical Nomenclature in Eur. J. Biochem., 1984, 138, 9-37 and J. Biol. Chem., 1989, 264, 633-673. The following additional abbreviations are used: AAA, amino acid analysis; All, allyl; Boc, tert-butoxycarbonyl; BOP, benzotriazole-1-yl-oxy-tris-(dimethylamino)phosphonium hexafluorophosphate; Bzl, benzyl; CI, chemical ionization; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCC, dicyclohexylcarbodiimide; DCM, dichloromethane; DIEA, N,N-diisopropylethylamine; DIPCDI, 1,3-diisopropylcarbodiimide; DMAP, 4-dimethylaminopyridine; DMF, dimethylformamide; Dnp, 2,4-dinitrophenyl; Fm, 9-fluorenylmethyl; Fmoc, 9-fluorenylmethyloxycarbonyl; GC-MS, gas chromatography-mass spectrometry; HOBt, 1-hydroxybenzotriazole; HPLC, high performance liquid chromatography; IR, infrared spectroscopy; MALDI-TOF, matrix-assisted laser desorption ionization/time-of-flight, MBHA, p-methylbenzhydrylamine; NMR, nuclear magnetic resonance, PyBOP, benzotriazole-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate; Su, succinimidyl; TBTU, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; TFA, trifluoroacetic acid; Tos, p-toluenesulfonyl. The amino acid symbols used denote the L configuration.
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23. Partial deprotection of His takes place during the DBU treatment. The presence of low levels of free His during the cyclization step does not seem to affect significantly the quality of the final product.