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Toward the Design of Molecular Chameleons: Flexible Shielding of an Amide Bond Enhances Macrocycle Cell Permeability
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0002-8880-9247
AstraZeneca, Early Prod Dev, IMED Biotech Unit, Pharmaceut Sci, Gothenburg, Sweden.
AstraZeneca, Early Prod Dev, IMED Biotech Unit, Pharmaceut Sci, Gothenburg, Sweden.
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2018 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 18, p. 5737-5742Article in journal (Refereed) Published
Abstract [en]

A series of macrocycles inspired by natural products were synthesized to investigate how side-chains may shield amide bonds and influence cell permeability. NMR spectroscopy and X-ray crystallography revealed that the phenyl group of phenylalanine, but not the side-chains of homologous or aliphatic amino acids, shields the adjacent amide bond through an intramolecular NH-pi interaction. This resulted in increased cell permeability, suggesting that NH-pi interactions may be used in the design of molecular chameleons.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2018. Vol. 20, no 18, p. 5737-5742
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-368110DOI: 10.1021/acs.orglett.8b02447ISI: 000445711500048PubMedID: 30207734OAI: oai:DiVA.org:uu-368110DiVA, id: diva2:1268401
Funder
Swedish Research Council, 2016-05160AstraZenecaAvailable from: 2018-12-05 Created: 2018-12-05 Last updated: 2018-12-05Bibliographically approved

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Tyagi, MohitPoongavanam, VasanthanathanKihlberg, Jan

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