Synthesis and conformation of fluorinated beta-peptidic compounds

Victoria Peddie, Raymond J Butcher, Ward T Robinson, Matthew C Wilce, Daouda A K Traore, Andrew D Abell

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Experimental and theoretical data indicate that, for alpha-fluoroamides, the FCC(O)N(H) moiety adopts an antiperiplanar conformation. In addition, a gauche conformation is favoured between the vicinal CF and CN(CO) bonds in N-beta-fluoroethylamides. This study details the synthesis of a series of fluorinated beta-peptides (1-8) designed to use these stereoelectronic effects to control the conformation of beta-peptide bonds. X-ray crystal structures of these compounds revealed the expected conformations: with fluorine beta to a nitrogen adopting a gauche conformation, and fluorine alpha to a CO group adopting an antiperiplanar conformation. Thus, the strategic placement of fluorine can control the conformation of a beta-peptide bond, with the possibility of directing the secondary structures of beta-peptides.
Original languageEnglish
Pages (from-to)6655 - 6662
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number21
DOIs
Publication statusPublished - 2012

Cite this

Peddie, Victoria ; Butcher, Raymond J ; Robinson, Ward T ; Wilce, Matthew C ; Traore, Daouda A K ; Abell, Andrew D. / Synthesis and conformation of fluorinated beta-peptidic compounds. In: Chemistry - A European Journal. 2012 ; Vol. 18, No. 21. pp. 6655 - 6662.
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abstract = "Experimental and theoretical data indicate that, for alpha-fluoroamides, the FCC(O)N(H) moiety adopts an antiperiplanar conformation. In addition, a gauche conformation is favoured between the vicinal CF and CN(CO) bonds in N-beta-fluoroethylamides. This study details the synthesis of a series of fluorinated beta-peptides (1-8) designed to use these stereoelectronic effects to control the conformation of beta-peptide bonds. X-ray crystal structures of these compounds revealed the expected conformations: with fluorine beta to a nitrogen adopting a gauche conformation, and fluorine alpha to a CO group adopting an antiperiplanar conformation. Thus, the strategic placement of fluorine can control the conformation of a beta-peptide bond, with the possibility of directing the secondary structures of beta-peptides.",
author = "Victoria Peddie and Butcher, {Raymond J} and Robinson, {Ward T} and Wilce, {Matthew C} and Traore, {Daouda A K} and Abell, {Andrew D}",
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Synthesis and conformation of fluorinated beta-peptidic compounds. / Peddie, Victoria; Butcher, Raymond J; Robinson, Ward T; Wilce, Matthew C; Traore, Daouda A K; Abell, Andrew D.

In: Chemistry - A European Journal, Vol. 18, No. 21, 2012, p. 6655 - 6662.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Synthesis and conformation of fluorinated beta-peptidic compounds

AU - Peddie, Victoria

AU - Butcher, Raymond J

AU - Robinson, Ward T

AU - Wilce, Matthew C

AU - Traore, Daouda A K

AU - Abell, Andrew D

PY - 2012

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AB - Experimental and theoretical data indicate that, for alpha-fluoroamides, the FCC(O)N(H) moiety adopts an antiperiplanar conformation. In addition, a gauche conformation is favoured between the vicinal CF and CN(CO) bonds in N-beta-fluoroethylamides. This study details the synthesis of a series of fluorinated beta-peptides (1-8) designed to use these stereoelectronic effects to control the conformation of beta-peptide bonds. X-ray crystal structures of these compounds revealed the expected conformations: with fluorine beta to a nitrogen adopting a gauche conformation, and fluorine alpha to a CO group adopting an antiperiplanar conformation. Thus, the strategic placement of fluorine can control the conformation of a beta-peptide bond, with the possibility of directing the secondary structures of beta-peptides.

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