High-pressure-promoted Fmoc-aminoacylation of N-ethylcysteine: preparation of key devices for the solid-phase synthesis of peptide thioesters

2010 ◽  
Vol 51 (2) ◽  
pp. 407-410 ◽  
Author(s):  
Yuko Nakahara ◽  
Ichiro Matsuo ◽  
Yukishige Ito ◽  
Risa Ubagai ◽  
Hironobu Hojo ◽  
...  
Keyword(s):  
High Pressure ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Peptide Thioesters

Fmoc Solid-Phase Synthesis of C-Terminal Peptide Thioesters by Formation of a Backbone Pyroglutamyl Imide Moiety

2009 ◽  
Vol 48 (40) ◽  
pp. 7411-7414 ◽  
Author(s):  
A. Pernille Tofteng ◽  
Kasper K. Sørensen ◽  
Kilian W. Conde-Frieboes ◽  
Thomas Hoeg-Jensen ◽  
Knud J. Jensen
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Peptide Thioesters

Fmoc Solid-Phase Synthesis of C-Terminal Peptide Thioesters by Formation of a Backbone Pyroglutamyl Imide Moiety

2009 ◽  
Vol 121 (40) ◽  
pp. 7547-7550 ◽  
Author(s):  
A. Pernille Tofteng ◽  
Kasper K. Sørensen ◽  
Kilian W. Conde-Frieboes ◽  
Thomas Hoeg-Jensen ◽  
Knud J. Jensen
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Peptide Thioesters

Fmoc Solid-Phase Synthesis of Peptide Thioesters by Masking as Trithioortho Esters

2003 ◽  
Vol 5 (16) ◽  
pp. 2951-2953 ◽  
Author(s):  
Jesper Brask ◽  
Fernando Albericio ◽  
Knud J. Jensen
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Peptide Thioesters

Fmoc Solid-Phase Synthesis of Peptide Thioesters Using an IntramolecularN,S-Acyl Shift

2005 ◽  
Vol 7 (13) ◽  
pp. 2647-2650 ◽  
Author(s):  
Nathalie Ollivier ◽  
Jean-Bernard Behr ◽  
Ouafâa El-Mahdi ◽  
Annick Blanpain ◽  
Oleg Melnyk
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Peptide Thioesters

Synthesis of Casein-Related Peptides and Phosphopeptides. XIII. Solid Phase Synthesis of GLu-Ser(P)-Leu Through Global Phosphorylation of a Resin-Bound Seryl-Containing Peptide

1991 ◽  
Vol 44 (4) ◽  
pp. 503 ◽  
Author(s):  
JW Perich ◽  
RB Johns
Keyword(s):  
High Pressure ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Palladium Acetate ◽  
Acid Oxidation ◽  
Butyl Ether ◽  
Ether Group ◽  
Phase Synthesis ◽  
Polystyrene Resin ◽  
Phosphate Protection

The solid phase synthesis of CF3CO2H.H-Glu-Ser(P)-Leu-OH by the 'global' 'phosphite-triester' phosphorylation of a polystyrene resin-bound seryl -containing peptide by using either dibenzyl or di -t-butyl N,N- diethylphosphoramidite is described. The seryl -containing peptide resin was prepared by successive dicyclohexylcarbodiimide/1H-benzotriazol-1-ol couplings of Fmoc -Ser(But)-OH and Z- Glu ( OBzl )-OH to Boc-Leu-resin (polystyrene) followed by cleavage of the seryl t-butyl ether group with 90% CF3CO2H/CH2Cl2. The seryl hydroxy group was phosphorylated by the use of either dibenzyl or di -t-butyl N,N-diethylphosphoramidite/1H- tetrazole followed by m-chloroperoxybenzoic acid oxidation of the resultant phosphite triester. With benzyl phosphate protection, the protected Ser(PO3Bzl2)-containing peptide resin was deprotected by high-pressure hydrogenation with palladium acetate. In the case of t-butyl phosphate protection, the t-butyl groups were first cleaved by treatment with 10% CF3CO2H/CH2Cl2 and the Ser(PO3H2) tripeptide was then cleaved from the resin support by high-pressure hydrogenation in the presence of palladium acetate.

An improved deblocking agent for direct Fmoc solid-phase synthesis of peptide thioesters

2002 ◽  
Vol 43 (13) ◽  
pp. 2419-2422 ◽  
Author(s):  
Xianzhang Bu ◽  
Guiyang Xie ◽  
Chi Wang Law ◽  
Zhihong Guo
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Peptide Thioesters
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