Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones

被引：57

作者：

Salas-Ambrosio, Pedro ^{[1
]}

Tronnet, Antoine ^{[2
,3
]}

Since, Marc ^{[4
]}

Bourgeade-Delmas, Sandra ^{[5
]}

Stigliani, Jean-Luc ^{[2
]}

Vax, Amelie ^{[1
]}

Lecommandoux, Sebastien ^{[1
]}

Dupuy, Bruno ^{[3
]}

Verhaeghe, Pierre ^{[2
]}

Bonduelle, Colin ^{[1
]}

机构：

[1] Univ Bordeaux, LCPO, Bordeaux INP, CNRS,UMR 5629, F-33600 Pessac, France

[2] Univ Toulouse, UPS, CNRS, LCC CNRS,UPR8241, F-31400 Toulouse, France

[3] Univ Paris, Inst Pasteur, LPBA, UMR CNRS 2001, F-75724 Paris, France

[4] Normandie Univ, CERMN, UNICAEN, F-14000 Caen, France

[5] Univ Toulouse, UPS, UMR PHARMA DEV 152, IRD, F-31400 Toulouse, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 10期

关键词：

35;

D O I：

10.1021/jacs.0c13231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclic polymers display unique physicochemical and biological properties. However, their development is often limited by their challenging preparation. In this work, we present a simple route to cyclic poly(alpha-peptoids) from N-alkylated-N-carboxyanhydrides (NNCA) using LiHMDS promoted ring-expansion polymerization (REP) in DMF. This new method allows the unprecedented use of lysine-like monomers in REP to design bioactive macrocycles bearing pharmaceutical potential against Clostridioides difficile, a bacterium responsible for nosocomial infections.

引用

页码：3697 / 3702

页数：6

共 35 条

[1] Synthesis and characterization of macrocyclic vinyl-aromatic polymers. Molecular weight-dependent glass transition temperatures and emission of macrocyclic polystyrene [J].

Alberty, KA ;

Hogen-Esch, TE ;

Carlotti, S .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 2005, 206 (10) :1035-1042

[2] An "endless" route to cyclic polymers [J].

Bielawski, CW ;

Benitez, D ;

Grubbs, RH .

SCIENCE, 2002, 297 (5589) :2041-2044

[3] STATIC AND DYNAMIC SCATTERING FROM CYCLIC DIBLOCK COPOLYMER CHAINS IN SOLUTION [J].

BORSALI, R ;

BENMOUNA, M .

MACROMOLECULAR SYMPOSIA, 1994, 79 :153-166

[4] Scattering properties of rod-coil and once-broken rod block copolymers [J].

Borsali, R ;

Lecommandoux, S ;

Pecora, R ;

Benoît, H .

MACROMOLECULES, 2001, 34 (12) :4229-4234

[5] UNSTABLE MESOIONIC OXAZOLIUM-5-OXIDES [J].

BOYD, GV ;

WRIGHT, PH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (07) :914-&

[6]

CDC, Antibiotic Resistance in Healthcare

[7] Polypeptoid polymers: Synthesis, characterization, and properties [J].

Chan, Brandon A. ;

Xuan, Sunting ;

Li, Ang ;

Simpson, Jessica M. ;

Sternhagen, Garrett L. ;

Yu, Tianyi ;

Darvish, Omead A. ;

Jiang, Naisheng ;

Zhang, Donghui .

BIOPOLYMERS, 2018, 109 (01)

[8] Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts [J].

Culkin, Darcy A. ;

Jeong, Wonhee ;

Csihony, Szilard ;

Gomez, Enrique D. ;

Balsara, Nitash R. ;

Hedrick, James L. ;

Waymouth, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) :2627-2630

[9] Controlled ring-opening polymerisation of cyclic esters: polymer blocks in self-assembled nanostructures [J].

Dove, Andrew P. .

CHEMICAL COMMUNICATIONS, 2008, (48) :6446-6470

[10]

Gingrich H.L., 2008, Chemistry of Heterocyclic Compounds, P731

← 1 2 3 4 →