cas 944283-07-2, Boc-Ser(Fmoc-Ala)-OH | Articles data

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Synthesis of cyclic peptides via O-N-acyl migration
We describe here a novel and convenient synthesis of head-to-tail cyclic peptide avoiding racemization. Linear depsipeptides including a serine residue as the key element for ester bond formation and acyl transfer were synthesized on 2-chlorotrityl chloride resin. After cleavage from the resin, intramolecular head-to-tail cyclization was performed in solution by C-terminal activation of urethane protected O-acyl serine residue. After removal of the Nα-serine protecting group, the final step consisted in O-N-acyl migration reaction on the 'switch' or 'click' element to restore native cyclic peptides.
Lécaillon, Jennifer,Gilles, Pierre,Subra, Gilles,Martinez, Jean,Amblard, Muriel
p. 4674 - 4676
(2008/12/20)

"o-Acyl isopeptide method" for peptide synthesis: Synthesis of forty kinds of "o-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH
The O-acyl isopeptide method has recently received attention as an efficient synthetic method for peptides. Herein, forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH (1-40) were effectively synthesized in two-steps without epimerization. The O-acyl isodipeptide units are important building blocks to enable the routine use of the O-acyl isopeptide method. This journal is The Royal Society of Chemistry.
Yoshiya, Taku,Taniguchi, Atsuhiko,Sohma, Youhei,Fukao, Fukue,Nakamura, Setsuko,Abe, Naoko,Ito, Nui,Skwarczynski, Mariusz,Kimura, Tooru,Hayashi, Yoshio,Kiso, Yoshiaki
p. 1720 - 1730
(2008/02/10)