128421-95-4Relevant articles and documents
Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction
Falkiewicz, Bogdan,Ko?odziejczyk, Aleksandra S,Liberek, Bogdan,Wi?niewski, Kazimierz
, p. 7909 - 7917 (2007/10/03)
Peptide nucleic acids (PNAs) are intensively studied DNA analogues. We elaborated an efficient procedure for the synthesis of N-, C-protected pseudodipeptides with a reduced peptide bond and then peptide nucleic acid (PNA) monomers, based on the Mitsunobu reaction of N-Boc-β-amino alcohols with N-o-nitrobenzenesulfonyl-protected (oNBS-protected) amino acid esters. Using the new procedure, we obtained protected PNA monomer backbones with various amino acid side chains. The pseudodipeptide secondary amine groups were then deprotected by thiolysis, and after appropriate work-up, acylated with thymin-1-ylacetic acid to give the protected monomers. The procedure seems to be of general applicability and allows various modifications of PNA structure by using diverse alcohols and amino acid esters.
Synthesis of new chiral peptide nucleic acid (PNA) monomers by a simplified reductive amination method
Falkiewicz, Bogdan,Kowalska, Katarzyna,Kolodziejczyk, Aleksandra S.,Wisniewski, Kazimierz,Lankiewicz, Leszek
, p. 353 - 361 (2007/10/03)
The aim of this work was the preparation of four new peptide nucleic acid (PNA) monomer backbone by reductive amination of N(α)-Boc-protected chiral amino aldehydes, derived from Leu, Phe, Tyr(Bzl), and Thr(Bzl), with methyl glycinate. To the crude 2-subs
An improved method for the preparation of desoxopeffides - Reductions of endothiopeptides
Guziec Jr., Frank S.,Wasmund, Loide Mayer
, p. 23 - 26 (2007/10/02)
Three new procedures for the synthesis of desoxopeptides from endothiopeptides are reported: 1) Raney nickel desulfurizafion, 2) alkylation with triethyloxonium tetrafluoroborate followed by sodium borohydride reduction, and 3) nickel boride reduction. Of