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

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

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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; Andersen, Jeanette Marker; Frydenvang, Karla Andrea; Nielsen, John.

In: European Journal of Organic Chemistry, Vol. 2014, No. 19, 2014, p. 3971-3975.

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

Harvard

Hjelmgaard, T, Plesner, M, Dissing, MM, Andersen, JM, Frydenvang, KA & Nielsen, J 2014, 'Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains', European Journal of Organic Chemistry, vol. 2014, no. 19, pp. 3971-3975. https://doi.org/10.1002/ejoc.201402040

APA

Hjelmgaard, T., Plesner, M., Dissing, M. M., Andersen, J. M., Frydenvang, K. A., & Nielsen, J. (2014). Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains. European Journal of Organic Chemistry, 2014(19), 3971-3975. https://doi.org/10.1002/ejoc.201402040

Vancouver

Hjelmgaard T, Plesner M, Dissing MM, Andersen JM, Frydenvang KA, Nielsen J. Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains. European Journal of Organic Chemistry. 2014;2014(19):3971-3975. https://doi.org/10.1002/ejoc.201402040

Author

Hjelmgaard, Thomas ; Plesner, Malene ; Dissing, Mette Marie ; Andersen, Jeanette Marker ; Frydenvang, Karla Andrea ; Nielsen, John. / Advances towards aromatic oligoamide foldamers : synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains. In: European Journal of Organic Chemistry. 2014 ; Vol. 2014, No. 19. pp. 3971-3975.

Bibtex

@article{cb986258d2964399bf7b715533e06d68,
title = "Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains",
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",
volume = "2014",
pages = "3971--3975",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "19",

}

RIS

TY - JOUR

T1 - Advances towards aromatic oligoamide foldamers

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

VL - 2014

SP - 3971

EP - 3975

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 19

ER -

ID: 127672067