Expedient solution-phase synthesis and NMR studies of arylopeptoids

TY - JOUR

T1 - Expedient solution-phase synthesis and NMR studies of arylopeptoids

AU - Hjelmgaard, Thomas

AU - Faure, Sophie

AU - Stærk, Dan

AU - Taillefumier, Claude

AU - Nielsen, John

PY - 2011/8

Y1 - 2011/8

N2 - The development of a highly convenient and efficient protocol for iterative solution-phase synthesis of shorter oligomers of para-and meta-arylopeptoids is described. Peptide coupling methods for accessing longer oligomers were studied: use of the new coupling reagent COMU was found to be the most efficient for creation of the tertiary benzamide bonds. The cis/trans isomerism of arylopeptoid backbones was studied by NMR and was found to be highly dependent on the nature of the side chains. Increasing bulkiness of theside chains favored the cis amide bond conformation; arylopeptoids possessing tert-butyl side chains contained exclusively cis amide bonds.

AB - The development of a highly convenient and efficient protocol for iterative solution-phase synthesis of shorter oligomers of para-and meta-arylopeptoids is described. Peptide coupling methods for accessing longer oligomers were studied: use of the new coupling reagent COMU was found to be the most efficient for creation of the tertiary benzamide bonds. The cis/trans isomerism of arylopeptoid backbones was studied by NMR and was found to be highly dependent on the nature of the side chains. Increasing bulkiness of theside chains favored the cis amide bond conformation; arylopeptoids possessing tert-butyl side chains contained exclusively cis amide bonds.

U2 - 10.1002/ejoc.201100232

DO - 10.1002/ejoc.201100232

M3 - Journal article

SN - 1434-193X

VL - 2011

SP - 4121

EP - 4132

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 22

ER -