U. Pedersen, M. Thorsen, E. El-Khrisy
1982
Citations
0
Influential Citations
18
Citations
Journal
Tetrahedron
Abstract
Abstract The easily accessible 2,4-bis (4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, LR , has been reacted with salts of N-protected amino acids 1 (Z-Gly-OH, Boc-Gly-OH, Boc-S-Ser(Bzl)-OH, Boc-S-Tyr(Bzl)-OH, Z-S-Arg(Z2)-OH, and Z-S-Pro-OH), at room temperature in CH2Cl2 to give the intermediates 2 , mixed anhydrides. When 2 is treated with two moles of a base and one mole of the salt of an amino acid ester 3 (TosOH·H-Gly-OBzl, HCl·H-Gly-OBzl, HCl·H-Gly-OEt, and HCl·H-S-Phe-OtBu) at 0°C, the expected peptide 4 is isolated in high yields. LR is also found to be a useful reagent in a fragment coupling between Z-Gly-S-Ala-OH and TosOH·H-S-Leu-OBzl). This tripeptide was tested by means of HPLC (deprotection and amino acid analysis according to Izumiya was not necessary), and no epimerization (