Versatile Oligo(N‐substituted) Glycines: The Many Roles of Peptoids in Drug Discovery

Abstract

Organic chemistry Z 0200 Versatile Oligo(N-substituted) Glycines: The Many Roles of Peptoids in Drug Discovery -[79 refs.]. -(PATCH, J. A.; KIRSHENBAUM, K.; SEURYNCK, S. L.; ZUCKERMANN, R. N.; BARRON, A. E.; Pseudo-Pept. Drug Discovery 2004, 1-31; Germany; Eng.) -Lindner 36-265

Antimicrobial Activities of Twenty Lysine-Peptoid Hybrids against Clinically Relevant Bacteria and Fungi

“…One way to circumvent this problem is to incorporate non-natural building blocks into the peptide. Peptoids are oligomers composed of N-substituted glycines [9] . These peptidomimetic oligomers are based on the peptide backbone.…”

Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids

“…Reaction of 1 (8.41 g, 20.5 mmol) following method A yielded 1a (10.8 g, 90%) as a pale yellowish oil. Then reaction of 1a (5.27 g, 9.00 mmol) following method B and performing the flash column chromatography with EtOAc/MeOH 97 : 3 as eluent until the impurities had passed followed by change to CH 2 Cl 2 /MeOH 97 : 3 yielded 2 (5.33 g, 79%) as a pale yellowish solid: 3,172.1,171.3,171.2,171.1,171.0,170.9,170.8,170.6,170.3,170.2,170.0,170.0,169.7,168.3,168.0,167.9,167.8,167.6,167.4,167.0,166.9 (4C,4¥C O),144.8 (C,Ph),140.6,140.5,140.3,140.2,140.0,139.9,139.7,139.4,139.2,139.0 (3C,Ph),128.9,128.6,128.6,128.4,128.0,127.8,127.5,127.4,127.3,126.9,126.8,126.7,126.5,126.4,126.0,125.9 (20CH,Ph), 80.4, 80.2 (C, t Bu), 58.4,58.4,…”

“…This journal is © The Royal Society of Chemistry 2012 144.5, 144.2 (C, Ph), 140.8, 140.6, 140.5, 140.4, 140.3, 140.2, 140.1, 140.0, 139.9, 139.7, 139.6, 139.4, 139.4, 139.2, 139.2, 139.1, 139.0, 138.6 (5C, Ph), 128.8, 128.6, 128.4, 128.1, 127.7, 127.6, 127.5, 127.4, 127.3, 127.2, 127.1, 126.8, 126.7, 126.6, 126.5, 126.4 (30CH, Ph), 58.5, 58.4, 58.2, 58.0 (CH, HNCHCH 3 ), 55.6, 55.5, 55.2, 55.0, 54.9, 54.8, 54.6, 54.6, 54.4, 54.3, 54.3, 54.0, 54.0, 53.8, 53.8 (2.71CH, NCHCH 3 ), 52. 3,52.0,51.9,51.7,51.6,51.6,51.4,51.3,51.0,50.9,50.7 (2.29CH,NCHCH 3 ),48.8,48.8,48.5,48.5 (CH 2 ,HNCH 2 C O), 45.6,45.3,45.1,45.1,44.9,44.8,44.6,44.3,44.2,43.9,43.8 (2CH 2 ,2NCH 2 C O), 41.2, 41. 1,41.0,40.7,40.6,40.3,40.3,40.1,39.9,39.7,39.3,39.2,39.1,38.9,38.8 (3CH 2 , 3¥NCH 2 CH 2 C O), 36.5, 36.3, 36.2, 35.9, 35.8, 35.5, 35.4, 35.2, 35.0, 34.9, 34.8, 34.4, 34.2, 34.1, 33.9, 33.8, 33.7, 33.5, 33.4, 33.3, 32.5, 32.3, 32.2, 32.0 (3CH 2 ,3¥NCH 2 CH 2 C O), 24.4,…”

“…1,35.9,35.9,35.8,35.7,35.6,35.5 (CH 2 28.4 (3CH 3 ,Boc), 18.1,17.8,16.3 (2CH 3 ,2¥NCHCH 3 ); n max /cm -1 2979, 1700 (C O, Boc), 1665 (C O, amide), 1654 (C O, amide), 1496,1449,1399,1365,1331,1276,1254,1215,1166,1136,1071,1043,1028,997,953,918,864,811,787,762,748 m,PhH), 6.64-6.08 (0.22H, m, NH 2 ), 6.08-5.70 (1.49H, m, NCHCH 3 ), 5.70-5.10 (2.75H, m, 0.89¥NH 2 and 0.97¥NCHCH 3 ), 5.00-4.58 (1.54H, m, NCHCH 3 ), 4.48-3.02 (8H, m, 2¥NCH 2 C Oa n d2 ¥NCH 2 CH 2 C O), 2.86-2.00 (4H, m, 2¥NCH 2 CH 2 C O), 1.70-1.23 (21H, m, 4¥NCHCH 3 and Boc); 13 C NMR (100 MHz, CDCl 3 ): d 174. 3,174.0,172.2,171.8,171.5,171.4,169.2,168.9,168.7,168.6,168.0,167.8,167.6 (4C,4¥C O),155.9,155.7,…”

Peptoids: Emerging Therapeutics for Neurodegeneration

“…Intranasal administration of peptoids also achieves effective delivery to the CNS, enabling use as a therapeutic for neurodegenerative diseases [16][17][18] . Additionally, peptoids are less likely than peptides to elicit an immunogenic response while retaining the ability to specifically target and inhibit protein-protein interactions 19,20 . Together, these characteristics render peptoids an attractive, novel neurotherapeutic agent.…”