Preservation of the protective group under alkaline conditions by using CaCl2. Applications in peptide synthesis

作者: Robert Pascal , Régine Sola

DOI: 10.1016/S0040-4039(98)00994-0

关键词: Combinatorial chemistryOrganic chemistryChemistryHydrolysisSaponificationAlkaline hydrolysisGroup (periodic table)Peptide synthesisPeptideLinkerCatalysis

摘要: Abstract CaCl 2 is shown to dramatically increase the lifetime of Fmoc protective group in alkaline iPrOH-H O but has little effect on hydrolytic processes. This enables efficient preparation Fmoc-protected peptide segments by saponification corresponding C-terminal methyl or benzyl esters. Similarly, protected prepared Fmoc/tBu solid-phase synthesis can be selectively released from support -catalyzed hydrolysis an N-acylurea-based linker.

参考文章(17)
Fernando Albericio, Ernest Giralt, Paul Lloyd-Williams, Chemical Approaches to the Synthesis of Peptides and Proteins ,(1997)
Louis A. Carpino, The 9-fluorenylmethyloxycarbonyl family of base-sensitive amino-protecting groups Accounts of Chemical Research. ,vol. 20, pp. 401- 407 ,(1987) , 10.1021/AR00143A003
Régine Sola, Jean Méry, Robert Pascal, Fmoc-based solid-phase peptide synthesis using dpr(phoc) linker. Synthesis of a C-terminal proline peptide Tetrahedron Letters. ,vol. 37, pp. 9195- 9198 ,(1996) , 10.1016/S0040-4039(96)02154-5
Chongwei Yue, Josiane Thierry, Pierre Potier, 2-phenyl isopropyl esters as car☐yl terminus protecting groups in the fast synthesis of peptide fragments Tetrahedron Letters. ,vol. 34, pp. 323- 326 ,(1993) , 10.1016/S0040-4039(00)60578-6
Tony Johnson, Martin Quibell, Robert C. Sheppard, N,O‐bisFmoc derivatives of N‐(2‐hydroxy‐4‐methoxybenzyl)‐amino acids: Useful intermediates in peptide synthesis Journal of Peptide Science. ,vol. 1, pp. 11- 25 ,(1995) , 10.1002/PSC.310010104
Michael Caplow, Studies of the mechanism of biotin catalysis. Journal of the American Chemical Society. ,vol. 87, pp. 5774- 5785 ,(1965) , 10.1021/JA00952A045
Jean E. Rivier, Garland R. Marshall, Peptides: Chemistry, Structure and Biology ,(1990)