Access to poly-beta-peptides with functionalized side chains and end groups via controlled ring-opening polymerization of beta-lactams

Journal of the American Chemical Society
Jihua ZhangShannon S Stahl

Abstract

Poly-beta-peptides are attractive for biomedical applications because the backbone is similar enough to that of proteins for biocompatibility, but the backbone is sufficiently unnatural that these polymers evade proteolytic degradation. Prior investigations of poly-beta-peptides have been hindered by two principal limitations: (1) most known examples are insoluble, and (2) the range of accessible side chain functionality has been quite limited (mostly simple hydrocarbon units). The present study describes innovations in poly-beta-peptide synthesis that enable the preparation of diversely functionalized examples and provide the basis for broad exploration of the properties and applications of these nylon-3 materials. We describe several beta-lactams with a protected amino group in their side chain that readily undergo ring-opening polymerization (ROP). These monomers are available in large quantities via N-chlorosulfonylisocyanate (CSI) cycloaddition reactions with functionalized alkenes; previously CSI reactions have been limited to alkenes with hydrocarbon substituents. Postpolymerization deprotection of the amino groups leads to water-soluble poly-beta-peptides. In addition, we introduce a simple co-initiation strategy that a...Continue Reading

References

Aug 10, 2000·Biopolymers·A TossiA Giangaspero
Sep 20, 2001·Journal of the American Chemical Society·J Cheng, T J Deming
Nov 17, 2001·Chemical Reviews·R P ChengW F DeGrado
Nov 17, 2001·Chemical Reviews·K Y Lee, D J Mooney
Jan 25, 2002·Nature·Michael Zasloff
Apr 2, 2004·Nature·Robert Langer, David A Tirrell
Oct 20, 2005·Biopolymers·Dieter SeebachAlice Glättli
Jan 31, 2006·Angewandte Chemie·Rainer Haag, Felix Kratz
Jul 13, 2006·Annual Review of Biomedical Engineering·Derek M Dykxhoorn, Judy Lieberman
Sep 28, 2006·Journal of the American Chemical Society·Amy J KarlssonSean P Palecek
Dec 13, 2006·Nature Biotechnology·Robert E W Hancock, Hans-Georg Sahl
Sep 1, 2007·Science·Kristi L Kiick
Nov 24, 2007·Journal of the American Chemical Society·Brendan P MowerySamuel H Gellman
Apr 9, 2008·Antimicrobial Agents and Chemotherapy·Radeekorn AkkarawongsaCurtis R Brandt

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Citations

Mar 30, 2012·Biomacromolecules·Runhui LiuSamuel H Gellman
Jan 6, 2011·Journal of the American Chemical Society·Hanxiang Zeng, Zhibin Guan
Sep 4, 2012·Journal of the American Chemical Society·Eric L Dane, Mark W Grinstaff
Nov 6, 2009·Journal of the American Chemical Society·Myung-Ryul LeeKristyn S Masters
May 21, 2010·Journal of the American Chemical Society·Michelle T DohmAnnelise E Barron
Jul 5, 2012·Journal of Drug Targeting·Zong-Wei WuShu-Yi Lin
Mar 8, 2014·Journal of the American Chemical Society·Runhui LiuSamuel H Gellman
Jul 30, 2015·Biomaterials Science·G T QinC Z Cai
May 25, 2012·Journal of Biomedical Materials Research. Part a·Runhui LiuKristyn S Masters
Jul 26, 2017·Antimicrobial Agents and Chemotherapy·Leslie A RankChristina M Hull
Feb 16, 2020·Angewandte Chemie·Min ZhouRunhui Liu
Feb 6, 2015·Macromolecular Rapid Communications·Jagadeesh MalineniMartin Möller
Mar 21, 2019·Macromolecular Rapid Communications·Paul N StockmannVolker Sieber
Jan 1, 2014·Chemical Science·Eric L DaneMark W Grinstaff
Aug 23, 2012·Chemical Communications : Chem Comm·Li ChenScott McN Sieburth
Sep 22, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yueming WuRunhui Liu
Jan 27, 2021·Nature Communications·Qi ChenRunhui Liu
Feb 23, 2021·Journal of the American Chemical Society·Lei LiuSamuel H Gellman
Mar 20, 2021·ACS Infectious Diseases·Joshua B JonesShonna M McBride
Jul 16, 2009·Journal of the American Chemical Society·Brendan P MowerySamuel H Gellman
Jan 29, 2013·ACS Macro Letters·Jihua ZhangSamuel H Gellman
Sep 30, 2010·The Journal of Organic Chemistry·Ram N RamNem Singh
Dec 2, 2014·Molecular Pharmaceutics·Venkatareddy NaditheOlivia M Merkel
Apr 4, 2013·Journal of the American Chemical Society·Runhui LiuSamuel H Gellman
Jun 21, 2014·Journal of the American Chemical Society·Sarah E StidhamMark W Grinstaff
Dec 17, 2016·The Journal of Organic Chemistry·Gerardo M TorresBruce A Arndtsen
Aug 28, 2020·The Journal of Organic Chemistry·Anant S BalijepalliMark W Grinstaff
Oct 2, 2014·Journal of the American Chemical Society·Saswata ChakrabortySamuel H Gellman
Oct 7, 2021·Advanced Materials·Kenward JungCyrille Boyer

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