Citation: Yueming Wu, Min Zhou, Kang Chen, Sheng Chen, Ximian Xiao, Zhemin Ji, Jingcheng Zou, Runhui Liu. Alkali-metal hexamethyldisilazide initiated polymerization on alpha-amino acid N-substituted N-carboxyanhydrides for facile polypeptoid synthesis[J]. Chinese Chemical Letters, ;2021, 32(5): 1675-1678. doi: 10.1016/j.cclet.2021.02.039 shu

Alkali-metal hexamethyldisilazide initiated polymerization on alpha-amino acid N-substituted N-carboxyanhydrides for facile polypeptoid synthesis

Yueming Wu ^a ,
Min Zhou ^b ,
Kang Chen ^b ,
Sheng Chen ^b ,
Ximian Xiao ^b ,
Zhemin Ji ^b ,
Jingcheng Zou ^b ,
Runhui Liu ^{a, b, *,}

a.
State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
Key Laboratory for Ultrafine Materials of Ministry of Education, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Research Center for Biomedical Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

rliu@ecust.edu.cn

Received Date: 5 February 2021
Revised Date: 18 February 2021
Accepted Date: 19 February 2021
Available Online: 22 February 2021

Figures(5)

Polypeptoids have been explored as mimics of polypeptides, owing to polypeptoids' superior stability upon proteolysis. Polypeptoids can be synthesized from one-pot ring-opening polymerization of amino acid N-substituted N-carboxyanhydrides (NNCAs). However, the speed of polymerization of NNCAs can be very slow, especially for NNCAs bearing a bulky N-substitution group. This hindered the exploration on polypeptoids with more diverse structures and functions. Therefore, it is in great need to develop advanced strategies that can accelerate the polymerization on inactive NNCAs. Hereby, we report that lithium/sodium/potassium hexamethyldisilazide (Li/Na/KHMDS) initiates a substantially faster poly-merization on NNCAs than do commonly used amine initiators, especially for NNCAs with bulky N-substitution group. This fast NNCA polymerization will increase the structure diversity and application of polypeptoids as synthetic mimics of polypeptides.
- Polypeptoids,
- Peptide mimics,
- N-Substituted N-carboxyanhydrides (NNCA),
- Lithium hexamethyldisilazide,
- Sodium hexamethyldisilazide,
- Potassium hexamethyldisilazide,
- Ring-opening polymerization,
- Inactive NNCA
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