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A S-Sn Lewis Pair-Mediated Ring-Opening Polymerization of alpha-Amino Acid N-Carboxyanhydrides: Fast Kinetics, High Molecular Weight, and Facile Bioconjugation
Yuan, Jingsong; Zhang, Yi; Li, Zezhou; Wang, Yaoyi; Lu, Hua
2018-08-01
Source PublicationACS MACRO LETTERS
ISSN2161-1653
Volume7Issue:8Pages:892-897
AbstractThe rapid and controlled generation of poly peptides with ultrahigh molecular weight (MW) and well defined chain end functionality has been a great challenge. To tackle this problem, we report here an initiation system based on a S-Sn Lewis pair, trimethylstannyl phenyl sulfide (PhS-SnMe3), for the ring-opening polymerization (ROP) of alpha-amino acid N-carboxyanhydrides (NCAs). This initiator displays a strong solvent effect, and can yield polypeptides with high MW (>1.0 x 10(5) g.mol(-1)) and low polydispersity index within a few hours. The MWs of the obtained polypeptides are strongly dependent on the THE/DMF ratio. The polymerization follows a typical first-order kinetic character with respect to the monomer concentration in mixed THE and DMF. Moreover, a highly reactive phenyl thioester is in situ generated at the C-terminus of the polypeptides, which is readily accessible for native chemical ligation affording high MW and site-specific protein polypeptide conjugates. Together, this initiator sheds light on regulating the ROP of NCAs via appropriate Lewis pair and solvent selection, and is particularly useful in preparing ultrahigh MW polypeptides within a short period of time.
DOI10.1021/acsmacrolett.8b00465
Indexed BySCI
Language英语
WOS IDWOS:000444659000001
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:3[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/43014
Collection中国科学院化学研究所
Corresponding AuthorLu, Hua
AffiliationPeking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Ctr Soft Matter Sci & Engn,Key Lab Polymer Chem &, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Yuan, Jingsong,Zhang, Yi,Li, Zezhou,et al. A S-Sn Lewis Pair-Mediated Ring-Opening Polymerization of alpha-Amino Acid N-Carboxyanhydrides: Fast Kinetics, High Molecular Weight, and Facile Bioconjugation[J]. ACS MACRO LETTERS,2018,7(8):892-897.
APA Yuan, Jingsong,Zhang, Yi,Li, Zezhou,Wang, Yaoyi,&Lu, Hua.(2018).A S-Sn Lewis Pair-Mediated Ring-Opening Polymerization of alpha-Amino Acid N-Carboxyanhydrides: Fast Kinetics, High Molecular Weight, and Facile Bioconjugation.ACS MACRO LETTERS,7(8),892-897.
MLA Yuan, Jingsong,et al."A S-Sn Lewis Pair-Mediated Ring-Opening Polymerization of alpha-Amino Acid N-Carboxyanhydrides: Fast Kinetics, High Molecular Weight, and Facile Bioconjugation".ACS MACRO LETTERS 7.8(2018):892-897.
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