Telechelic Triblock Poly(α‐Amino Acid)‐Poly(Tetrahydrofuran)‐Poly(α‐Amino Acid) Copolymers: Chain‐End Transformation, Polymerization and pH‐Responsive Hydrolysis†. Issue 10 (15th August 2021)

• Record Type: Journal Article
• Authors: Zhou, Peng; Li, Zixian; Lu, Yanzhi; Kong, Jie; Ling, Jun
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 10(2021)
• Page Start: 2852
• Page End: 2856
• Publication Date: 2021-08-15
• Subjects: End group transformation -- Block copolymers -- Amino acid -- Peptides -- Peptoids; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100319
• Languages: English
• ISSNs: 1001-604X

Abstract

Main observation and conclusion: Block copolymers not only combine properties of different segments but also generate new application prospects. Poly(α‐amino acid)‐ b ‐poly(tetrahydrofuran)‐ b ‐poly(α‐amino acid) (PAA‐PTHF‐PAA) is one of the copolymers. In this contribution, di‐hydroxyl‐ended HO‐PTHF‐OH is transferred into di‐oxyamino‐ended H2 NO‐PTHF‐ONH2 quantitatively, which is used as a macroinitiator to polymerize sarcosine N ‐thiocarboxyanhydride (Sar‐NTA) and N ‐phenyoxycarbonyl N ‐ε‐carbobenzyloxy‐ D ‐lysine (ZDL‐NPC). Well‐defined triblock PAA‐NHO‐PTHF‐ONH‐PAA is produced with high molecular weight (up to 25.3 kg/mol) and narrow dispersity. The amphiphilic PSar‐NHO‐PTHF‐ONH‐PSar (STS) self‐assembles into micelles with uniform diameters of 30—40 nm according to DLS. Owing to oxygen amide groups inside the backbone of these copolymers, the polyether‐poly(amino acid)s block copolymers are cleavable under an acidic environment and therefore have potential applications in smart biomedicine and engineering. Abstract : Transformation of chain‐end hydroxyl groups of poly(tetrahydrofuran) (PTHF) into oxyamino groups through Mitsunobu reaction is presented here. Comparable to alkyl amine, the oxyamine of PTHF is able to initiate sarcosine N ‐thiocarboxyanhydride and N ‐phenyoxycarbonyl N ‐ε‐carbobenzyloxy‐ D ‐lysine, forming three block copolymers which contain poly(α‐amino acid)s and are pH‐responsive.