Quaternary centres as a tool for modulating foldamer conformation

Roberta Galeazzi; Gianluca Martelli; Andrea Mazzanti; Mario Orena; Samuele Rinaldi

doi:10.1002/chem.201102103

Quaternary centres as a tool for modulating foldamer conformation

Roberta Galeazzi, Gianluca Martelli, Andrea Mazzanti, Mario Orena, Samuele Rinaldi

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

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

Abstract

Centre refold: (3R,4S,1′S)-4-Amino-1-(1′-(4-methoxyphenyl) ethyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid (AMMOPC) gives a foldamer with an 8-helix conformation. When it was inserted in the 12-helix foldamer of (3R,4S,1′S)-4-amino-1-(1′-(4-methoxyphenyl)ethyl) -5-oxo-pyrrolidine-3-carboxylic acid (AMOPC), it locally induced formation of an 8-helix conformation (see figure).

Original language	English
Pages (from-to)	12564-12568
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	45
DOIs	https://doi.org/10.1002/chem.201102103
Publication status	Published - Nov 4 2011

Keywords

conformation analysis
foldamers
helical structures
lactams
quaternary carbon

ASJC Scopus subject areas

Chemistry(all)

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10.1002/chem.201102103

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title = "Quaternary centres as a tool for modulating foldamer conformation",

abstract = "Centre refold: (3R,4S,1′S)-4-Amino-1-(1′-(4-methoxyphenyl) ethyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid (AMMOPC) gives a foldamer with an 8-helix conformation. When it was inserted in the 12-helix foldamer of (3R,4S,1′S)-4-amino-1-(1′-(4-methoxyphenyl)ethyl) -5-oxo-pyrrolidine-3-carboxylic acid (AMOPC), it locally induced formation of an 8-helix conformation (see figure).",

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T1 - Quaternary centres as a tool for modulating foldamer conformation

AU - Galeazzi, Roberta

AU - Martelli, Gianluca

AU - Mazzanti, Andrea

AU - Orena, Mario

AU - Rinaldi, Samuele

PY - 2011/11/4

Y1 - 2011/11/4

N2 - Centre refold: (3R,4S,1′S)-4-Amino-1-(1′-(4-methoxyphenyl) ethyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid (AMMOPC) gives a foldamer with an 8-helix conformation. When it was inserted in the 12-helix foldamer of (3R,4S,1′S)-4-amino-1-(1′-(4-methoxyphenyl)ethyl) -5-oxo-pyrrolidine-3-carboxylic acid (AMOPC), it locally induced formation of an 8-helix conformation (see figure).

AB - Centre refold: (3R,4S,1′S)-4-Amino-1-(1′-(4-methoxyphenyl) ethyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid (AMMOPC) gives a foldamer with an 8-helix conformation. When it was inserted in the 12-helix foldamer of (3R,4S,1′S)-4-amino-1-(1′-(4-methoxyphenyl)ethyl) -5-oxo-pyrrolidine-3-carboxylic acid (AMOPC), it locally induced formation of an 8-helix conformation (see figure).

KW - conformation analysis

KW - foldamers

KW - helical structures

KW - lactams

KW - quaternary carbon

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