C6-Substituted methanopyrrolidine β-amino acid: synthesis and characterization of oligomeric foldamers

Zilun Hu; Guoliang Lin; Matthew Sender; Kevin C. Cannon; Franklin A. Davis; Grant R. Krow

doi:10.1016/j.tetlet.2020.152240

C6-Substituted methanopyrrolidine β-amino acid: synthesis and characterization of oligomeric foldamers

Zilun Hu
, Guoliang Lin
, Matthew Sender
, Kevin C. Cannon
, Franklin A. Davis
, Grant R. Krow

Division of Engineering and Science (Abington)

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Highly conformation constrained β-proline based methanopyrrolidine-5-carboxylic acids (6, MetPyr-5-acids, or MetPyr-β-amino acids) derivatives were designed, synthesized, and investigated to control peptide conformation and oligomer folding. Enhanced order of folding uniformity correlated with length of the prepared homo-oligomers as characterized by circular dichroism (CD). The octamer (34) exhibited minimal solvent effects and was stable with increasing temperature up to 80 °C. Substitutions on C6 of the 2-azabicyclo[2.1.1] hexane structure could modulate the amide cis/trans conformation.

Original language	English (US)
Article number	152240
Journal	Tetrahedron Letters
Volume	61
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2020.152240
State	Published - Aug 27 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.152240

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title = "C6-Substituted methanopyrrolidine β-amino acid: synthesis and characterization of oligomeric foldamers",

abstract = "Highly conformation constrained β-proline based methanopyrrolidine-5-carboxylic acids (6, MetPyr-5-acids, or MetPyr-β-amino acids) derivatives were designed, synthesized, and investigated to control peptide conformation and oligomer folding. Enhanced order of folding uniformity correlated with length of the prepared homo-oligomers as characterized by circular dichroism (CD). The octamer (34) exhibited minimal solvent effects and was stable with increasing temperature up to 80 °C. Substitutions on C6 of the 2-azabicyclo[2.1.1] hexane structure could modulate the amide cis/trans conformation.",

author = "Zilun Hu and Guoliang Lin and Matthew Sender and Cannon, \{Kevin C.\} and Davis, \{Franklin A.\} and Krow, \{Grant R.\}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

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doi = "10.1016/j.tetlet.2020.152240",

language = "English (US)",

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T1 - C6-Substituted methanopyrrolidine β-amino acid

T2 - synthesis and characterization of oligomeric foldamers

AU - Hu, Zilun

AU - Lin, Guoliang

AU - Sender, Matthew

AU - Cannon, Kevin C.

AU - Davis, Franklin A.

AU - Krow, Grant R.

PY - 2020/8/27

Y1 - 2020/8/27

N2 - Highly conformation constrained β-proline based methanopyrrolidine-5-carboxylic acids (6, MetPyr-5-acids, or MetPyr-β-amino acids) derivatives were designed, synthesized, and investigated to control peptide conformation and oligomer folding. Enhanced order of folding uniformity correlated with length of the prepared homo-oligomers as characterized by circular dichroism (CD). The octamer (34) exhibited minimal solvent effects and was stable with increasing temperature up to 80 °C. Substitutions on C6 of the 2-azabicyclo[2.1.1] hexane structure could modulate the amide cis/trans conformation.

AB - Highly conformation constrained β-proline based methanopyrrolidine-5-carboxylic acids (6, MetPyr-5-acids, or MetPyr-β-amino acids) derivatives were designed, synthesized, and investigated to control peptide conformation and oligomer folding. Enhanced order of folding uniformity correlated with length of the prepared homo-oligomers as characterized by circular dichroism (CD). The octamer (34) exhibited minimal solvent effects and was stable with increasing temperature up to 80 °C. Substitutions on C6 of the 2-azabicyclo[2.1.1] hexane structure could modulate the amide cis/trans conformation.

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DO - 10.1016/j.tetlet.2020.152240

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

C6-Substituted methanopyrrolidine β-amino acid: synthesis and characterization of oligomeric foldamers

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