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Award Abstract # 1308485
Poly(alpha-hydroxy acids) via Ring-Opening Polymerization of O-Carboxyanhydrides

NSF Org: CHE
Division Of Chemistry
Recipient: UNIVERSITY OF ILLINOIS
Initial Amendment Date: September 8, 2013
Latest Amendment Date: September 8, 2013
Award Number: 1308485
Award Instrument: Standard Grant
Program Manager: George Janini
CHE
 Division Of Chemistry
MPS
 Directorate for Mathematical and Physical Sciences
Start Date: September 15, 2013
End Date: August 31, 2018 (Estimated)
Total Intended Award Amount: $390,000.00
Total Awarded Amount to Date: $390,000.00
Funds Obligated to Date: FY 2013 = $390,000.00
History of Investigator:
  • Jianjun Cheng (Principal Investigator)
    jianjunc@uiuc.edu
Recipient Sponsored Research Office: University of Illinois at Urbana-Champaign
506 S WRIGHT ST
URBANA
IL  US  61801-3620
(217)333-2187
Sponsor Congressional District: 13
Primary Place of Performance: University of Illinois at Urbana-Champaign
506 S. Wright Street
Urbana
IL  US  61801-3620
Primary Place of Performance
Congressional District:
13
Unique Entity Identifier (UEI): Y8CWNJRCNN91
Parent UEI: V2PHZ2CSCH63
NSF Program(s): Macromolec/Supramolec/Nano
Primary Program Source: 01001314DB NSF RESEARCH & RELATED ACTIVIT
Program Reference Code(s):
Program Element Code(s): 688500
Award Agency Code: 4900
Fund Agency Code: 4900
Assistance Listing Number(s): 47.049

ABSTRACT

In this project funded by the Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division of the National Science Foundation, Jianjun Cheng at the University of Illinois at Urbana-Champaign aims to develop methods for facile preparation of poly(alpha-hydroxy acids) bearing pendant functionalities. The project will first focus on the design and synthesis of various O-carboxyanhydride monomers containing natural or unnatural amino acid side chains. These monomers will then be used in the development of organo- and metal-catalyzed, living ring-opening polymerization of O-carboxyanhydrides to yield well-defined poly(alpha-hydroxy acids) with functionalized side chains. Finally, some applications of poly(alpha-hydroxy acids), such as their uses in encapsulation, conjugation and membrane penetration, will be explored. The broader impacts and proposed education and outreach activities include mentoring academically underperforming undergraduate students and leading summer education and outreach programs designed for stimulating interest of high school and college students in science and engineering.

Polyesters are useful materials encountered in many aspects of everyday life: clothing fiber, plastic bottles, plastic shopping bags, etc. One drawback of many commercial polyesters is that they are not easily modified to form new materials with new properties. In this research project, new classes of polyesters that incorporate different types of chemical groups are developed. Such materials could impact a range of technologies in which plastics are used, such as new technologies for recycling of polyester plastics, the generation of renewable plastics and new functional materials for biomedical applications.

PUBLICATIONS PRODUCED AS A RESULT OF THIS RESEARCH

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(Showing: 1 - 10 of 14)
Azzi, J.; Yin, Q.; Uehara, M.; Ohori, S.; Tang, L.; Cai, K; Ichimura, T.; McGrath, M.; Maarouf, M.; Kefaloyianni, E.; Loughhead, S.; Petr, J.; Sun, Q.; Kwon, M.; Tullius, M.; Andrian, U.; Cheng, J.; Abdi, R. "Targeted delivery of immunomodulators to lymph nodes" Cell Reports , v.15 , 2016 , p.1202 10.1016/j.celrep.2016.04.007
Baumgartner, R., Fu, H.; Song, Z.; Lin, Y.; Cheng, J. "Cooperative polymerization of ?-helices induced by macromolecular architecture" Nature Chemistry , v.9 , 2017 , p.614 10.1038/nchem.2712
Fatih M. Uckun, Lloyd G. Mitchell, Sanjive Qazi, Yang Liu, Nan Zheng, Dorothea E. Myers, Ziyuan Song, Hong Ma, Jianjun Cheng "Development of Polypeptide-based Nanoparticles for Non-viral Delivery of CD22 RNA Trans-splicing Molecule as a New Precision Medicine Candidate Against B-lineage ALL" EBioMedicine , 2015 10.1016/j.ebiom.2015.04.016
Qian Yin, Lichen Yin, Hua Wang, Jianjun Cheng* "Synthesis and Biomedical Applications of Functional Poly(?-hydroxy acids) via Ring-Opening Polymerization of O?Carboxyanhydrides" Accounts of Chemical Research , 2015 10.1021/ar500455z
Ren, Y.; Baumgartner, R.; Fu, H.; Schoot, P.V.D.; Cheng, J.; Lin, Y. "Revisiting the Helical Cooperativity of Synthetic Polypeptides in Solution" Biomacromolecules , v.18 , 2017 , p.2324 10.1021/acs.biomac.7b00534
Ren, Y.; Fu, H.; Baumgartner, R.; Zhang, Y.; Cheng, J.; Lin, Y. "Folding Cooperativity of Synthetic Polypeptides with or without ?Tertiary? Interactions" ACS Macro Letter , v.6 , 2017 , p.733 10.1021/acsmacrolett.7b00324
Ruibo Wang, Jiawei Zhang, Qian Yin, Yunxiang Xu, Jianjun Cheng*, Rong Tong* "Controlled Ring-Opening Polymerization of O-Carboxyanhydrides Using ?-Diiminate Zinc Catalyst" Angewandte Chemie International Edition , v.55 , 2016 , p.13010 10.1002/anie.201605508
Song, Z.; Fu, H.; Wang, R.; Pacheco, L.A.; Wang, X.; Lin, Y.; Cheng, J. "Secondary structures in synthetic polypeptides from N-carboxyanhydrides: design, modulation, association, and material applications" Chemical Society Reviews , v.47 , 2018 , p.7401 10.1039/C8CS00095F
Song, Z.; Han, Z.; Lv, S.; Chen, C.; Chen, L.; Lin, Y.; Cheng, J. "Synthetic polypeptides: from polymer design to supramolecular assembly and biomedical application" Chemical Society Reviews , v.46 , 2017 , p.6570 10.1039/C7CS00460E
Song, Ziyuan and Fu, Hailin and Wang, Ruibo and Pacheco, Lazaro A. and Wang, Xu and Lin, Yao and Cheng, Jianjun "Secondary structures in synthetic polypeptides from N -carboxyanhydrides: design, modulation, association, and material applications" Chemical Society Reviews , v.47 , 2018 10.1039/c8cs00095f Citation Details
Song, Z.; Mansbach, R.A.; He, H.; Shik, K.C.; Baumgartner, R.; Zheng, N.; Ba, X.; Huang, Y.; Mani, D.; Nieh, M.P.; Ferguson, A.L.; Yin, L.; Cheng, J. "Modulation of Polypeptide Conformation through Donor-Acceptor Transformation of Side-Chain Hydrogen Bonding Ligands" Nature Communication , v.8 , 2017 , p.92 10.1038/s41467-017-00079-5
(Showing: 1 - 10 of 14)

PROJECT OUTCOMES REPORT

Disclaimer

This Project Outcomes Report for the General Public is displayed verbatim as submitted by the Principal Investigator (PI) for this award. Any opinions, findings, and conclusions or recommendations expressed in this Report are those of the PI and do not necessarily reflect the views of the National Science Foundation; NSF has not approved or endorsed its content.

Degradable polymers such as polyesters and polypeptides are materials that we see, touch and use almost every day in our life. To give a few examples, numerous clothing, plastic bottles for beverage, plastic shopping bags, sleep bags, high strength ropes and hoses are made of these polymers.  One drawback of these conventional polymers is that we cannot easily modify them to achieve new properties because they typically do not have chemical groups that can be used for property modification.  In the proposed research, we aimed to develop new synthetic strategies for the access of a large variety of these degradable polymers that not only have unprecedented, new properties and but also have chemical groups that can be used for structure and chemical modification to achieve other properties.  We developed a library of building blocks and catalysts that can allow for preparation of these special polymers with any desirable and uniform length, with properties suitable for bio-applications.  We also explored the fundamental studies of the structure-function correlation, their direct use as therapeutic materials, and applications such as making small devices capable of on-demand release of cargos or bacteria-resistant fabric.  We published a total of nine papers in leading journals such as Nature Communications, Journal of American Chemical Society, and Proceedings of the National Academy of Sciences.  


Last Modified: 03/29/2019
Modified by: Jianjun Cheng

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