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Vezina-Dawod S.,Laval University | Derson A.,Laval University | Biron E.,Chu Of Quebec Research Center Chul Section
Tetrahedron Letters | Year: 2014

Peptoids (oligo . N-substituted glycines) are peptidomimetic oligomers showing attractive structural and pharmacological properties. The efficiency of their synthesis has prompted the use of peptoids in combinatorial libraries. To increase the chemical diversity accessible in peptoid design and libraries, we demonstrate here that . N-substituted . o-nitrobenzenesulfonamide derivatives can be used as alternative building blocks in the synthesis of peptoids by the submonomer approach. The preparation of . N,. O-protected amino alcohol submonomers and the conditions for their incorporation into peptoid oligomers are reported. The described method is compatible with the submonomer approach and was applied to prepare peptoid oligomers bearing different hydroxylated side chains. © 2014 Elsevier Ltd. Source


Vezina-Dawod S.,Laval University | Vezina-Dawod S.,Chu Of Quebec Research Center Chul Section | Derson A.,Laval University | Derson A.,Chu Of Quebec Research Center Chul Section | And 2 more authors.
Tetrahedron Letters | Year: 2015

Peptoids (oligo N-substituted glycines) are peptidomimetic oligomers showing attractive structural and pharmacological properties. The efficiency of their synthesis has prompted the use of peptoids in combinatorial libraries. To increase the chemical diversity accessible in peptoid design and libraries, we demonstrate here that N-substituted o-nitrobenzenesulfonamide derivatives can be used as alternative building blocks in the synthesis of peptoids by the submonomer approach. The preparation of N,O-protected amino alcohol submonomers and the conditions for their incorporation into peptoid oligomers are reported. The described method is compatible with the submonomer approach and was applied to prepare peptoid oligomers bearing different hydroxylated side chains. © 2014 Elsevier Ltd. All rights reserved. Source


Liang X.,Laval University | Liang X.,Chu Of Quebec Research Center Chul Section | Girard A.,Laval University | Girard A.,Chu Of Quebec Research Center Chul Section | And 2 more authors.
ACS Combinatorial Science | Year: 2013

The use of cyclic peptides in one-bead-one-compound libraries is limited by difficulties in sequencing hit compounds. Lacking a free N-terminal amine, such peptides cannot be sequenced by the Edman degradation approach, and complex fragmentation patterns are obtained by tandem mass spectrometry. To overcome this problem, we designed an alternative approach introducing a methionine residue within the macrocycle and as a linker to allow simultaneous ring-opening and release from the resin upon treatment with cyanogen bromide. The methionine linker was inverted relative to the peptide chain to allow the synthesis of cyclic peptides anchored by a lysine side chain and to avoid the presence of two C-terminal homoserine lactones on the released linear peptides. After MALDI-TOF MS/MS analysis, the peptides released from a single bead were sequenced manually and with a de novo sequencing software. The strategy described herein is compatible with commonly used amino acids and allows sequencing of cyclic peptides in one-bead-one-compound libraries, thus reducing the need for encoding. © 2013 American Chemical Society. Source

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