Undesired removal of the Fmoc group by the free ε-amino function of a lysine residue

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7813-7815

  Farrera Sinfreu, Josep ^a   Royo, Miriam ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; LYSINE; PEPTIDE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PEPTIDE SYNTHESIS; SOLID;

EID: 0037152301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01605-2     Document Type: Article

References (20)

1. . For a review on cyclic peptides, see: Rovero P. Kates S.A., Albericio F., Practical Solid-Phase Synthesis: A Book Companion. 2000;331-364 Marcel Dekker, New York.
2. Kates S.A., Daniels S.B., Albericio F. Anal. Biochem. 212:1993;303-310.
3. Braunitzer G., Schrank B., Petersen S., Petersen U. Hoppe-Seyler's Z. Physiol. Chem. 354:1973;1563-1566.
4. For reviews on solid-phase chemistry, see: (a) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Obrecht, D.; Villalgordo, J. M., Eds.; Pergamon: Oxford, 1998; (b) Combinatorial Chemistry: A Practical Approach; Bannwarth, W.; Felder, E., Eds.; Wiley-VCH: Weinheim, 2000; (c) Practical Solid-Phase Synthesis: A Book Companion; Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; (d) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wiley & Sons: New York, 2001.
5. For reviews on solid-phase chemistry, see: (a) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Obrecht, D.; Villalgordo, J. M., Eds.; Pergamon: Oxford, 1998; (b) Combinatorial Chemistry: A Practical Approach; Bannwarth, W.; Felder, E., Eds.; Wiley-VCH: Weinheim, 2000; (c) Practical Solid-Phase Synthesis: A Book Companion; Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; (d) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wiley & Sons: New York, 2001.
6. For reviews on solid-phase chemistry, see: (a) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Obrecht, D.; Villalgordo, J. M., Eds.; Pergamon: Oxford, 1998; (b) Combinatorial Chemistry: A Practical Approach; Bannwarth, W.; Felder, E., Eds.; Wiley-VCH: Weinheim, 2000; (c) Practical Solid-Phase Synthesis: A Book Companion; Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; (d) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wiley & Sons: New York, 2001.
7. For reviews on solid-phase chemistry, see: (a) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Obrecht, D.; Villalgordo, J. M., Eds.; Pergamon: Oxford, 1998; (b) Combinatorial Chemistry: A Practical Approach; Bannwarth, W.; Felder, E., Eds.; Wiley-VCH: Weinheim, 2000; (c) Practical Solid-Phase Synthesis: A Book Companion; Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; (d) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; John Wiley & Sons: New York, 2001.
8. . An orthogonal system is defined as a set of completely independent classes of protecting groups, such that each class of groups can be removed in any order and in the presence of all other classes. See: Barany G., Albericio F. J. Am. Chem. Soc. 107:1985;4936-4942. and references cited therein.
9. For a review on orthogonal protecting groups, see: Albericio F. Biopolymers (Peptide Sci.). 55:2000;123-139.
10. Aletras A., Barlos K., Gatos D., Koutsogianni S., Mamos P. Int. J. Peptide Protein Res. 45:1995;488-496.
11. For reviews on allyl-based protecting groups, see: Guibé F. Tetrahedron. 53:1997;13509-13556. and 1998, 54, 2967-3042.
12. Thieriet N., Alsina J., Giralt E., Guibé F., Albericio F. Tetrahedron Lett. 38:1997;7275-7278.
13. Gómez-Martínez P., Dessolin M., Guibé F., Albericio F. J. Chem. Soc., Perkin Trans. 1. 1999;2871-2874.
14. Kumar and Aldrich have observed a similar phenomenon during the removal of the Alloc group from the side-chain amino function of Lys. See: Kumar, V.; Aldrich, J. V. Abstr. Pap. Am. Chem. Soc. (2000), 220th ORGN-226.
15. The Ddz group is completely stable to piperidine and can be removed with a minimum of 1% of TFA, and therefore is removed during the final cleavage of the peptide from the resin. See: Birr C. Epton R., Innovation and Perspectives in Solid-Phase Synthesis. 1990;155-181 SPCC (UK) Ltd, Birmingham, UK.
16. Samples of 2 and 3 were unequivocally prepared as standards.
17. Gairí M., Lloyd-Williams P., Albericio F., Giralt E. Tetrahedron Lett. 31:1990;7363-7366.
18. Alsina J., Giralt E., Albericio F. Tetrahedron Lett. 37:1996;4195-4198.
19. Albericio F., Cases M., Alsina J., Triolo S.A., Carpino L.A., Kates S.A. Tetrahedron Lett. 38:1997;4853-4856.
20. For coupling without preactivation of the protected amino acid, phosphonium salts such as PyAOP are preferred to aminium/uronium salts, such as HATU, because the latter can lead to guanidinium formation. See: Albericio F., Bofill J.M., El-Faham A., Kates S.A. J. Org. Chem. 63:1998;9678-9683.