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

doi:10.1021/ol8022243

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

62 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 language	English
Pages (from-to)	5373-5376
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	23
DOIs	https://doi.org/10.1021/ol8022243
Publication status	Published - 2008 Dec 4

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Biased helical folding of chiral oligoindole foldamers",

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.",

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T1 - Biased helical folding of chiral oligoindole foldamers

AU - Naidu, Veluru Ramesh

AU - Kim, Min Cheol

AU - Suk, Jae Min

AU - Kim, Ho Joong

AU - Lee, Myongsoo

AU - Sim, Eunji

AU - Jeong, Kyu Sung

PY - 2008/12/4

Y1 - 2008/12/4

N2 - (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.

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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Biased helical folding of chiral oligoindole foldamers

Abstract

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