Adv Polym Sci (2013) 262: 389–414
DOI: 10.1007/12_2013_237
© Springer-Verlag Berlin Heidelberg 2013
Published online: 20 October 2013
Peptoids for Biomimetic Hierarchical
Structures
Niklas Gangloff and Robert Luxenhofer
Abstract Life as we know it is impossible without formation of hierarchical
structures. First and foremost, proteins, that is, sequence-specific polypeptides,
are nature
0 s vanguard in this respect. Peptoids and polypeptoids are structural
isomers and analogs to peptides and polypeptides. Here, we review the advancements over the last few years on biomimetic hierarchical structures obtained using
polypeptoids. Although the inherently more flexible amide bond in peptoids make
the stabilization of secondary structure challenging, it also gives us a tool to direct
the conformation of the amide bond by design. As will be seen, this is a particularly
important feature of peptoids.
Keywords High-precision polymer Á Secondary structure Á Self-assembly Á
Sequence-specific polymer Á Synthetic biology Á Tertiary structure
Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 390
2 Primary Structure: Synthetic Possibilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 392
2.1 Iterative Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . 392
2.2 Living Polymerization of N-Substituted N-Carboxyanhydrides . . . . . . . . . . . . . . . . . . . . 395
3 Secondary Structure Mimetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 396
3.1 Helices . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397
3.2 Loops, Turns, and Ribbons . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400
4 Tertiary Structure Mimetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 402
4.1 Globular Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 403
4.2 Multihelical Bundles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 404
N. Gangloff and R. Luxenhofer (*)
Functional Polymer Materials, Chair of Chemical Technology of Materials Synthesis,
University Wu ¨rzburg, Ro ¨ntgenring 11, 97070 Wu ¨rzburg, Germany
e-mail: robert.luxenhofer@uni-wuerzburg.de
DOI: 10.1007/12_2013_237
© Springer-Verlag Berlin Heidelberg 2013
Published online: 20 October 2013
Peptoids for Biomimetic Hierarchical
Structures
Niklas Gangloff and Robert Luxenhofer
Abstract Life as we know it is impossible without formation of hierarchical
structures. First and foremost, proteins, that is, sequence-specific polypeptides,
are nature
0 s vanguard in this respect. Peptoids and polypeptoids are structural
isomers and analogs to peptides and polypeptides. Here, we review the advancements over the last few years on biomimetic hierarchical structures obtained using
polypeptoids. Although the inherently more flexible amide bond in peptoids make
the stabilization of secondary structure challenging, it also gives us a tool to direct
the conformation of the amide bond by design. As will be seen, this is a particularly
important feature of peptoids.
Keywords High-precision polymer Á Secondary structure Á Self-assembly Á
Sequence-specific polymer Á Synthetic biology Á Tertiary structure
Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 390
2 Primary Structure: Synthetic Possibilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 392
2.1 Iterative Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . 392
2.2 Living Polymerization of N-Substituted N-Carboxyanhydrides . . . . . . . . . . . . . . . . . . . . 395
3 Secondary Structure Mimetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 396
3.1 Helices . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397
3.2 Loops, Turns, and Ribbons . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400
4 Tertiary Structure Mimetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 402
4.1 Globular Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 403
4.2 Multihelical Bundles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 404
N. Gangloff and R. Luxenhofer (*)
Functional Polymer Materials, Chair of Chemical Technology of Materials Synthesis,
University Wu ¨rzburg, Ro ¨ntgenring 11, 97070 Wu ¨rzburg, Germany
e-mail: robert.luxenhofer@uni-wuerzburg.de