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

被引：53

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
Alberty, KA
Hogen-Esch, TE
Carlotti, S
[J]. MACROMOLECULAR CHEMISTRY AND PHYSICS, 2005, 206 (10) : 1035 - 1042
[2] An "endless" route to cyclic polymers
Bielawski, CW
Benitez, D
Grubbs, RH
[J]. SCIENCE, 2002, 297 (5589) : 2041 - 2044
[3] STATIC AND DYNAMIC SCATTERING FROM CYCLIC DIBLOCK COPOLYMER CHAINS IN SOLUTION
BORSALI, R
BENMOUNA, M
[J]. MACROMOLECULAR SYMPOSIA, 1994, 79 : 153 - 166
[4] Scattering properties of rod-coil and once-broken rod block copolymers
Borsali, R
Lecommandoux, S
Pecora, R
Benoît, H
[J]. MACROMOLECULES, 2001, 34 (12) : 4229 - 4234
[5] UNSTABLE MESOIONIC OXAZOLIUM-5-OXIDES
BOYD, GV
WRIGHT, PH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (07): : 914 - &
[6] Center for Disease Control and Prevention (CDC), How Antibiotic Resistance Happens
[7] Polypeptoid polymers: Synthesis, characterization, and properties
Chan, Brandon A.
Xuan, Sunting
Li, Ang
Simpson, Jessica M.
Sternhagen, Garrett L.
Yu, Tianyi
Darvish, Omead A.
Jiang, Naisheng
Zhang, Donghui
[J]. BIOPOLYMERS, 2018, 109 (01)
[8] Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts
Culkin, Darcy A.
Jeong, Wonhee
Csihony, Szilard
Gomez, Enrique D.
Balsara, Nitash R.
Hedrick, James L.
Waymouth, Robert M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) : 2627 - 2630
[9] Controlled ring-opening polymerisation of cyclic esters: polymer blocks in self-assembled nanostructures
Dove, Andrew P.
[J]. CHEMICAL COMMUNICATIONS, 2008, (48) : 6446 - 6470
[10] Gingrich H.L., 2008, Chemistry of Heterocyclic Compounds, P731

← 1 2 3 4 →