Synthesis and conformational analysis of optically active poly(β-peptides)

Jianjun Cheng, Timothy J. Deming

Research output: Contribution to journalArticle

Abstract

Optically active poly(β-peptides) with proteinogenic side chains were synthesized via the polymerization of β-amino acid-N-carboxyanhydrides (β-NCAs) initiated using either NaOtBu or a nickel amido amidate complex. Although most of these low molecular weight poly(β-peptides) have poor solubility in common organic solvents, those that were soluble were found to adopt stable chiral conformations in solution. Poly(Nξ-carbobenzyloxy-β-L-homolysine) (2f) was observed to adopt a helical conformation in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), which could be disrupted by addition of methanesulfonic acid (MSA), a strong denaturing agent. The side-chain deprotected polymers, poly(β-L-homolysine) (3) and poly(β-L-homoglutamate) (4), were found to display pH-dependent conformation transitions in aqueous solution.

Original languageEnglish (US)
Pages (from-to)5169-5174
Number of pages6
JournalMacromolecules
Volume34
Issue number15
DOIs
StatePublished - Jul 17 2001
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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