Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains

Thomas Hjelmgaard; Malene Plesner; Mette Marie Dissing; Jeanette Marker Andersen; Karla Andrea Frydenvang; John Nielsen

doi:10.1002/ejoc.201402040

Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains

Thomas Hjelmgaard^*, Malene Plesner, Mette Marie Dissing, Jeanette Marker Andersen, Karla Andrea Frydenvang, John Nielsen

^*Corresponding author for this work

Department of Chemistry

7 Citations (Scopus)

Abstract

We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a "submonomer method" on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	19
Pages (from-to)	3971-3975
Number of pages	5
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201402040
Publication status	Published - 2014

Keywords

Amides
Foldamers
Solid-phase synthesis
Structure elucidation

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10.1002/ejoc.201402040

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Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains. / Hjelmgaard, Thomas; Plesner, Malene; Dissing, Mette Marie et al.
In: European Journal of Organic Chemistry, Vol. 2014, No. 19, 2014, p. 3971-3975.

Research output: Contribution to journal › Journal article › Research › peer-review

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abstract = "We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a {"}submonomer method{"} on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.",

keywords = "Amides, Foldamers, Solid-phase synthesis, Structure elucidation",

author = "Thomas Hjelmgaard and Malene Plesner and Dissing, {Mette Marie} and Andersen, {Jeanette Marker} and Frydenvang, {Karla Andrea} and John Nielsen",

year = "2014",

doi = "10.1002/ejoc.201402040",

language = "English",

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T2 - synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains

AU - Hjelmgaard, Thomas

AU - Plesner, Malene

AU - Dissing, Mette Marie

AU - Andersen, Jeanette Marker

AU - Frydenvang, Karla Andrea

AU - Nielsen, John

PY - 2014

Y1 - 2014

N2 - We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a "submonomer method" on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.

AB - We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a "submonomer method" on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.

KW - Amides

KW - Foldamers

KW - Solid-phase synthesis

KW - Structure elucidation

U2 - 10.1002/ejoc.201402040

DO - 10.1002/ejoc.201402040

M3 - Journal article

AN - SCOPUS:84903287384

SN - 1434-193X

VL - 2014

SP - 3971

EP - 3975

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains

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Keywords

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