Literature DB >> 31088971

Synthesis of polypeptides via bioinspired polymerization of in situ purified N-carboxyanhydrides.

Ziyuan Song1, Hailin Fu2,3, Jiang Wang4, Jingshu Hui5, Tianrui Xue5, Lazaro A Pacheco1, Haoyuan Yan6, Ryan Baumgartner5, Zhiyu Wang1, Yingchun Xia1, Xuefang Wang1, Lichen Yin7, Chongyi Chen1, Joaquín Rodríguez-López5, Andrew L Ferguson8, Yao Lin9,3, Jianjun Cheng10,5,7,11,12,13,14.   

Abstract

Ribozymes synthesize proteins in a highly regulated local environment to minimize side reactions caused by various competing species. In contrast, it is challenging to prepare synthetic polypeptides from the polymerization of N-carboxyanhydrides (NCAs) in the presence of water and impurities, which induce monomer degradations and chain terminations, respectively. Inspired by natural protein synthesis, we herein report the preparation of well-defined polypeptides in the presence of competing species, by using a water/dichloromethane biphasic system with macroinitiators anchored at the interface. The impurities are extracted into the aqueous phase in situ, and the localized macroinitiators allow for NCA polymerization at a rate which outpaces water-induced side reactions. Our polymerization strategy streamlines the process from amino acids toward high molecular weight polypeptides with low dispersity by circumventing the tedious NCA purification and the demands for air-free conditions, enabling low-cost, large-scale production of polypeptides that has potential to change the paradigm of polypeptide-based biomaterials.

Entities:  

Keywords:  N-carboxyanhydride; bioinspired polymerization; in situ purification; polypeptide; segregation

Year:  2019        PMID: 31088971      PMCID: PMC6561217          DOI: 10.1073/pnas.1901442116

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  30 in total

1.  Rapidly recovering hydrogel scaffolds from self-assembling diblock copolypeptide amphiphiles.

Authors:  Andrew P Nowak; Victor Breedveld; Lisa Pakstis; Bulent Ozbas; David J Pine; Darrin Pochan; Timothy J Deming
Journal:  Nature       Date:  2002-05-23       Impact factor: 49.962

2.  Nucleation-elongation: a mechanism for cooperative supramolecular polymerization.

Authors:  Dahui Zhao; Jeffrey S Moore
Journal:  Org Biomol Chem       Date:  2003-10-21       Impact factor: 3.876

3.  Synthesis and chemical properties of poly-alpha-amino acids.

Authors:  E KATCHALSKI; M SELA
Journal:  Adv Protein Chem       Date:  1958

4.  The ribosome as an entropy trap.

Authors:  Annette Sievers; Malte Beringer; Marina V Rodnina; Richard Wolfenden
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-12       Impact factor: 11.205

5.  Stimuli-responsive polypeptide vesicles by conformation-specific assembly.

Authors:  Enrico G Bellomo; Michael D Wyrsta; Lisa Pakstis; Darrin J Pochan; Timothy J Deming
Journal:  Nat Mater       Date:  2004-03-14       Impact factor: 43.841

6.  Mechanism of peptide bond synthesis on the ribosome.

Authors:  Stefan Trobro; Johan Aqvist
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-22       Impact factor: 11.205

7.  Reversible inside-out micellization of pH-responsive and water-soluble vesicles based on polypeptide diblock copolymers.

Authors:  Juan Rodríguez-Hernández; Sébastien Lecommandoux
Journal:  J Am Chem Soc       Date:  2005-02-23       Impact factor: 15.419

8.  Interfacial properties of adsorbed films made of a PEG2000 and PLA50 mixture or a copolymer at the dichloromethane-water interface.

Authors:  A Malzert; F Boury; P Saulnier; Tz Ivanova; I Panaïotov; J P Benoît; J E Proust
Journal:  J Colloid Interface Sci       Date:  2003-03-15       Impact factor: 8.128

9.  The formation of polymer vesicles or "peptosomes" by polybutadiene-block-poly(L-glutamate)s in dilute aqueous solution.

Authors:  Hildegard Kukula; Helmut Schlaad; Markus Antonietti; Stephan Förster
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

10.  Living polypeptides.

Authors:  Thrasyvoulos Aliferis; Hermis Iatrou; Nikos Hadjichristidis
Journal:  Biomacromolecules       Date:  2004 Sep-Oct       Impact factor: 6.988

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Authors:  Dylan T Holden; Nicolás M Morato; R Graham Cooks
Journal:  Proc Natl Acad Sci U S A       Date:  2022-10-03       Impact factor: 12.779

2.  Understanding Proton Transfer in Non-aqueous Biopolymers based on Helical Peptides: A Quantum Mechanical Study.

Authors:  Jiang Bian; Anthony Cruz; Gabriel López-Morales; Anton Kyrylenko; Donna McGregor; Gustavo E López
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Review 3.  Recent Advances in Poly(α-L-glutamic acid)-Based Nanomaterials for Drug Delivery.

Authors:  Yu Zhang; Wenliang Song; Yiming Lu; Yixin Xu; Changping Wang; Deng-Guang Yu; Il Kim
Journal:  Biomolecules       Date:  2022-04-25

4.  Induction of a higher-ordered architecture in glatiramer acetate improves its biological efficiency in an animal model of multiple sclerosis.

Authors:  Ziyuan Song; Yee Ming Khaw; Lazaro A Pacheco; Kuan-Ying Tseng; Zhengzhong Tan; Kaimin Cai; Ettigounder Ponnusamy; Jianjun Cheng; Makoto Inoue
Journal:  Biomater Sci       Date:  2020-09-30       Impact factor: 6.843

5.  Open-air synthesis of oligo(ethylene glycol)-functionalized polypeptides from non-purified N-carboxyanhydrides.

Authors:  Zhengzhong Tan; Ziyuan Song; Tianrui Xue; Lining Zheng; Lei Jiang; Yunjiang Jiang; Zihuan Fu; Anh Nguyen; Cecilia Leal; Jianjun Cheng
Journal:  Biomater Sci       Date:  2021-06-04       Impact factor: 7.590

Review 6.  Density Functional Theory Studies on the Synthesis of Poly(α-Amino Acid)s Via the Amine-Mediated Ring Opening Polymerizations of N-Carboxyanhydrides and N-Thiocarboxyanhydrides.

Authors:  Tianwen Bai; Botuo Zheng; Jun Ling
Journal:  Front Chem       Date:  2021-03-29       Impact factor: 5.221

7.  Substituent Effects Provide Access to Tetrasubstituted Ring-Opening Olefin Metathesis of Bicyclo[4.2.0]oct-6-enes.

Authors:  Gyusaang Youn; Nicole S Sampson
Journal:  ACS Org Inorg Au       Date:  2021-08-13

8.  Water-assisted and protein-initiated fast and controlled ring-opening polymerization of proline N-carboxyanhydride.

Authors:  Yali Hu; Zi-You Tian; Wei Xiong; Dedao Wang; Ruichi Zhao; Yan Xie; Yu-Qin Song; Jun Zhu; Hua Lu
Journal:  Natl Sci Rev       Date:  2022-02-24       Impact factor: 23.178

Review 9.  Polylysine for skin regeneration: A review of recent advances and future perspectives.

Authors:  Payam Zarrintaj; Sadegh Ghorbani; Mahmood Barani; Narendra Pal Singh Chauhan; Mohsen Khodadadi Yazdi; Mohammad Reza Saeb; Joshua D Ramsey; Michael R Hamblin; Masoud Mozafari; Ebrahim Mostafavi
Journal:  Bioeng Transl Med       Date:  2021-11-05
  9 in total

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