A versatile strategy for the synthesis of sequence-defined peptoids with side-chain and backbone diversity via amino acid building blocks

Chemical Science
Shixue WangXianhong Wang

Abstract

Designing artificial macromolecules with absolute sequence order is still a long-term challenge in polymer chemistry as opposed to natural biopolymers with perfectly defined sequences like proteins and DNA. Herein, we combined amino acid building blocks and iterative Ugi reactions for the de novo design and synthesis of sequence-defined peptoids. The highly efficient strategy provided excellent yields and enables multigram-scale synthesis of perfectly defined peptoids. This new strategy furnishes the broad structural diversity of side chains, as well as backbones. Importantly, the overall hydrophobicity and lower critical solution temperature (LCST) behaviours of these precisely defined peptoids can be logically altered by variation of the sequence. By following the same Ugi chemistry, these peptoids are also conjugated to DNA in a simple way, facilitating the development of novel therapeutics.

References

Nov 9, 2002·Organic Letters·Hernando J OlivosThomas Kodadek
Nov 13, 2003·Journal of the American Chemical Society·Daniel M Rosenbaum, David R Liu
Jul 20, 2007·Journal of the American Chemical Society·Sebastian Pfeifer, Jean-François Lutz
Jan 15, 2008·Journal of the American Chemical Society·Kenichi TakizawaCraig J Hawker
Mar 18, 2008·Journal of the American Chemical Society·Ralph E KleinerDavid R Liu
Sep 13, 2008·Current Opinion in Chemical Biology·Barney Yoo, Kent Kirshenbaum
Jun 16, 2009·Journal of the American Chemical Society·Sebastian PfeiferJean-François Lutz
May 8, 2010·Chemical Society Reviews·Nezha Badi, Jean-François Lutz
Mar 25, 2011·Macromolecular Rapid Communications·Sandra BinauldEric Drockenmuller
Jul 7, 2011·Current Pharmaceutical Design·Michelle T DohmAnnelise E Barron
Nov 24, 2011·Nature Chemistry·Makoto OuchiMitsuo Sawamoto
Aug 10, 2013·Science·Jean-François LutzMitsuo Sawamoto
Oct 1, 2013·Nature Communications·Guillaume GodySébastien Perrier
Oct 24, 2013·Nature Materials·Rosemary KanastyDaniel Anderson
Nov 1, 2013·Angewandte Chemie·Pieter EspeelAnnemieke Madder
Dec 7, 2013·Angewandte Chemie·Susanne C Solleder, Michael A R Meier
Mar 29, 2014·Angewandte Chemie·Thomas G W EdwardsonHanadi F Sleiman
Sep 11, 2014·Journal of the American Chemical Society·Mintu Porel, Christopher A Alabi
Apr 10, 2015·Advanced Materials·Abigail S KnightRonald N Zuckermann
May 7, 2015·Nature Communications·Jonas S LaursenChristian A Olsen
May 27, 2015·Nature Communications·Raj Kumar RoyJean-François Lutz
Jun 9, 2015·Journal of the American Chemical Society·Will R Gutekunst, Craig J Hawker
Jul 16, 2015·Accounts of Chemical Research·Jonas S LaursenChristian A Olsen
Aug 14, 2015·Proceedings of the National Academy of Sciences of the United States of America·Frank A LeibfarthTimothy F Jamison
Sep 24, 2015·Nature Chemistry·Jonathan C BarnesJeremiah A Johnson
Dec 15, 2015·Angewandte Chemie·Susanne C SollederMichael A R Meier
Dec 25, 2015·Chemical Reviews·Niklas GangloffRobert Luxenhofer
Jan 8, 2016·Accounts of Chemical Research·Ellen J RobertsonRonald N Zuckermann
May 25, 2016·Nature Chemistry·Mintu PorelChristopher A Alabi
Jul 2, 2016·Angewandte Chemie·Rosemary L KanastyDaniel G Anderson
Jul 14, 2016·Journal of the American Chemical Society·Yivan JiangJeremiah A Johnson
Jul 28, 2016·Journal of the American Chemical Society·Gianni CavalloJean-François Lutz
Nov 3, 2016·Journal of the American Chemical Society·Steven MartensPieter Espeel
Dec 3, 2016·Nature Communications·Nicolas ZydziakChristopher Barner-Kowollik
Dec 16, 2016·Journal of the American Chemical Society·Faheem AmirMichael J Monteiro
Jan 10, 2017·ACS Chemical Biology·Mintu PorelChristopher A Alabi
Mar 11, 2017·Nature Chemistry·Nikolaos G EngelisDavid M Haddleton
Mar 16, 2017·Macromolecular Rapid Communications·Susanne C SollederMichael A R Meier
Jun 14, 2017·Topics in Current Chemistry·Audrey LlevotMichael A R Meier
Sep 1, 2017·Journal of the American Chemical Society·Alexander E StrossChristopher A Hunter
Jan 23, 2018·Journal of the American Chemical Society·Matthew R GolderJeremiah A Johnson

❮ Previous
Next ❯

Citations

Oct 3, 2020·Macromolecular Rapid Communications·Guoqiang LiuLei Tao
Mar 20, 2019·Angewandte Chemie·Waldemar KonradChristopher Barner-Kowollik
May 16, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Sunting Xuan, Ronald N Zuckermann
Nov 24, 2020·Macromolecular Rapid Communications·Yue Tao, Youhua Tao
Nov 8, 2019·Acta Biomaterialia·Hannah R ReeseStefano Menegatti
Jun 3, 2021·Polymers·Chao GengHongda Wang
Feb 27, 2019·Biomacromolecules·Shixue WangXianhong Wang
Oct 7, 2021·Chemical Communications : Chem Comm·Claudine Nicole HerlanStefan Bräse
Sep 26, 2021·Macromolecular Rapid Communications·Botuo ZhengJun Ling

❮ Previous
Next ❯

Methods Mentioned

BETA
electrophoresis

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.