Biased helical folding of chiral oligoindole foldamers

Veluru Ramesh Naidu, Min Cheol Kim, Jae Min Suk, Ho Joong Kim, Myongsoo Lee, Eunji Sim, Kyu Sung Jeong

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

(Chemical Equation Presented) Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (S,S)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.

Original languageEnglish
Pages (from-to)5373-5376
Number of pages4
JournalOrganic Letters
Volume10
Issue number23
DOIs
Publication statusPublished - 2008 Dec 4

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Phenethylamines
Circular Dichroism
Scaffolds
Isomers
helices
folding
Anions
Conformations
Hydrogen
Hydrogen bonds
dichroism
isomers
hydrogen bonds
anions
1,4-bis(di(5-hydroxy-1H-indol-3-yl)methyl)benzene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Naidu, V. R., Kim, M. C., Suk, J. M., Kim, H. J., Lee, M., Sim, E., & Jeong, K. S. (2008). Biased helical folding of chiral oligoindole foldamers. Organic Letters, 10(23), 5373-5376. https://doi.org/10.1021/ol8022243
Naidu, Veluru Ramesh ; Kim, Min Cheol ; Suk, Jae Min ; Kim, Ho Joong ; Lee, Myongsoo ; Sim, Eunji ; Jeong, Kyu Sung. / Biased helical folding of chiral oligoindole foldamers. In: Organic Letters. 2008 ; Vol. 10, No. 23. pp. 5373-5376.
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Naidu, VR, Kim, MC, Suk, JM, Kim, HJ, Lee, M, Sim, E & Jeong, KS 2008, 'Biased helical folding of chiral oligoindole foldamers', Organic Letters, vol. 10, no. 23, pp. 5373-5376. https://doi.org/10.1021/ol8022243

Biased helical folding of chiral oligoindole foldamers. / Naidu, Veluru Ramesh; Kim, Min Cheol; Suk, Jae Min; Kim, Ho Joong; Lee, Myongsoo; Sim, Eunji; Jeong, Kyu Sung.

In: Organic Letters, Vol. 10, No. 23, 04.12.2008, p. 5373-5376.

Research output: Contribution to journalArticle

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AB - (Chemical Equation Presented) Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (S,S)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.

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Naidu VR, Kim MC, Suk JM, Kim HJ, Lee M, Sim E et al. Biased helical folding of chiral oligoindole foldamers. Organic Letters. 2008 Dec 4;10(23):5373-5376. https://doi.org/10.1021/ol8022243