Accelerated Polypeptide Synthesis via N-Carboxyanhydride Ring Opening Polymerization in Continuous Flow.

Macromolecular Rapid Communications
Jeroen Hendrik VrijsenGreg G Qiao

Abstract

In nature, polypeptide-based materials are ubiquitous, yet their synthetic production is hampered by high cost, limited scalability, and often stringent reaction conditions. Herein an elegant approach is presented for N-carboxyanhydride ring opening polymerization (NCA ROP) of Nε-benzyloxycarbonyl-l-lysine (ZLL) and γ-benzyl-l-glutamate (BLG) NCA in continuous flow. The polymerization is initiated by primary amine initiators using N,N-dimethylformamide (DMF) as solvent. Carrying out the reaction in a silicon microflow reactor speeds up the rate of ROP (92% conversion in 40 min in flow as opposed to 6 h in batch) due to highly efficient permeation of CO2 through the reactor tubing. The polymerization strategy provides a facile, scale-up friendly alternative to traditional batch mode polymerization and has the capability of streamlining NCA ROP.

References

Aug 1, 1971·European Journal of Immunology·D TeitelbaumM Sela
Feb 11, 1983·Science·I S Johnson
Sep 21, 2002·Chemical Communications : Chem Comm·J C van Hest, D A Tirrell
Sep 14, 2004·Biomacromolecules·Thrasyvoulos AliferisNikos Hadjichristidis
Jul 20, 2005·Lab on a Chip·Takeshi HondaHideaki Maeda
Jul 27, 2005·Current Opinion in Structural Biology·Robert Fairman, Karin S Akerfeldt
Aug 9, 2011·Journal of the American Chemical Society·Claire F HansellRachel K O'Reilly
Jan 31, 2012·Journal of Medicinal Chemistry·Laia Malet-Sanz, Flavien Susanne
Jul 7, 2015·Chemical Reviews·Timothy J Deming
Sep 18, 2015·Macromolecular Rapid Communications·Mark ByrneAndreas Heise
Oct 2, 2015·Beilstein Journal of Organic Chemistry·Marcus Baumann, Ian R Baxendale
Oct 19, 2016·Macromolecular Bioscience·Oleksandr ZagorodkoMaría J Vicent
Mar 1, 2017·Nature Chemical Biology·Alexander J MijalisBradley L Pentelute
Jun 24, 2017·Nature Chemistry·Ryan BaumgartnerJianjun Cheng
Sep 25, 2017·Scientific Reports·Víctor R Campos-GarcíaLuis F Flores-Ortiz
Sep 5, 2018·Colloids and Surfaces. B, Biointerfaces·Bo LiuXiaoyan Yuan
Oct 21, 2018·Chemistry, an Asian Journal·Shinichiro FuseHiroyuki Nakamura
Nov 30, 2018·Chemical Communications : Chem Comm·Faith M Akwi, Paul Watts
Feb 23, 2019·Journal of Medicinal Chemistry·Andrew R Bogdan, Amanda W Dombrowski
Oct 25, 2017·Polymers·Carmen M González-HenríquezJuan Rodríguez-Hernández
Apr 25, 2019·Journal of the American Chemical Society·Chongyi ChenJianjun Cheng
May 16, 2019·Proceedings of the National Academy of Sciences of the United States of America·Ziyuan SongJianjun Cheng
Aug 31, 2019·Chemistry : a European Journal·Shinichiro FuseHiroyuki Nakamura
Feb 6, 2020·ACS Applied Materials & Interfaces·Bingxin LiuGreg G Qiao

❮ Previous
Next ❯

Citations

Dec 8, 2020·Angewandte Chemie·Héctor Soria-CarreraRafael Martín-Rapún
Sep 26, 2021·Macromolecular Rapid Communications·Botuo ZhengJun Ling

❮ Previous
Next ❯

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.