TY - JOUR
T1 - Oligo(N-alkoxy glycines)
T2 - trans substantiating peptoid conformations.
AU - Jordan, Peter A.
AU - Paul, Bishwajit
AU - Butterfoss, Glenn L.
AU - Renfrew, P. Douglas
AU - Bonneau, Richard
AU - Kirshenbaum, Kent
PY - 2011
Y1 - 2011
N2 - Peptoid oligomers possess many desirable attributes bioactive peptidomimetic agents, including their ease of synthesis, chemical diversity, and capability for molecular recognition. Ongoing efforts to develop functional peptoids will necessitate improved capability for control of peptoid structure, particularly of the backbone amide conformation. We introduce alkoxyamines as a new reagent for solid phase peptoid synthesis. Herein, we describe the synthesis of N-alkoxy peptoids, and present NMR data indicating that the oligomers adopt a single stable conformation featuring trans amide bonds. These findings, combined with results from computational modeling, suggest that N-alkoxy peptoid oligomers have a strong propensity to adopt a polyproline II type secondary structure.
AB - Peptoid oligomers possess many desirable attributes bioactive peptidomimetic agents, including their ease of synthesis, chemical diversity, and capability for molecular recognition. Ongoing efforts to develop functional peptoids will necessitate improved capability for control of peptoid structure, particularly of the backbone amide conformation. We introduce alkoxyamines as a new reagent for solid phase peptoid synthesis. Herein, we describe the synthesis of N-alkoxy peptoids, and present NMR data indicating that the oligomers adopt a single stable conformation featuring trans amide bonds. These findings, combined with results from computational modeling, suggest that N-alkoxy peptoid oligomers have a strong propensity to adopt a polyproline II type secondary structure.
UR - http://www.scopus.com/inward/record.url?scp=84856067368&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84856067368&partnerID=8YFLogxK
U2 - 10.1002/bip.21675
DO - 10.1002/bip.21675
M3 - Article
C2 - 22180909
AN - SCOPUS:84856067368
SN - 0006-3525
VL - 96
SP - 617
EP - 626
JO - Biopolymers
JF - Biopolymers
IS - 5
ER -