50300-96-4Relevant articles and documents
Asymmetric α-2-tosylethenylation of N,N-dialkyl-l-amino acid esters via the formation of non-racemic ammonium enolates
Tayama, Eiji,Igarashi, Tomohito,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information; experimental part, p. 339 - 345 (2012/01/19)
Asymmetric α-2-tosylethenylation of (S)-2-(pyrrolidin-1-yl)propanoic acid esters was shown to produce good yields with high enantioselectivities. The reaction proceeds via the formation of a non-racemic ammonium enolate without an external source of chirality.
Derivatized Amino Acids Relevant to Native Peptide Synthesis by Chemical Ligation and Acyl Transfer
Clive, Derrick L. J.,Hisaindee, Soleiman,Coltart, Don M.
, p. 9247 - 9254 (2007/10/03)
Three amino acids were converted into the derivatives 5.2 (from glycine), 6.4a and 6.4b (from alanine), and 8.3a and 8.3b (from O-benzyl serine). These N-alkylated amino acids, which can be deprotected after conversion of the carboxyl into an amide, correspond to the general structure 2.1, a compound class of use in the study of peptide segment coupling by the ligation-acyl transfer method.
1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase
Li, Peng,Xu, Jie-Cheng
, p. 8119 - 8131 (2007/10/03)
1-Ethyl-2-halopyridinium salts, BEP, FEP, BEPH and FEPH, were synthesized and proved to be very effective for the synthesis of hindered peptides containing N-methylated or C(α),C(α)-dialkylated amino acid residues. HPLC monitoring of model reactions indicated that these pyridinium salts demonstrated higher reactivities, lower racemization than the commonly used halogenated uronium and phosphonium salts. The efficiency of these pyridinium type coupling reagents was further proved by the synthesis of a series of hindered oligopeptides and active esters with good yields and convenient workup. The 8-11 tetrapeptide fragment of Cyclosporin A (CsA) and the pentapeptide moiety of Dolastatin 15 were also successfully synthesized using these pyridinium salts. The efficiency of these pyridinium type coupling reagents for SPPS was also demonstrated by the solid-phase synthesis of the extremely hindered 8-11 peptide segment of CsA and the linear undecapeptide of CsO. The mechanism of the pyridinium salt mediated coupling reactions was also studied by 1H NMR, IR and HPLC. It was proposed that the major reactive intermediates were the corresponding acyl halide and acyloxypyridinium salts of the N-protected amino acid or peptide. (C) 2000 Elsevier Science Ltd.
