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 | |
| Publication status | Published - 2008 Dec 4 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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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 journal › Article
TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=61349145592&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=61349145592&partnerID=8YFLogxK
U2 - 10.1021/ol8022243
DO - 10.1021/ol8022243
M3 - Article
C2 - 18973333
AN - SCOPUS:61349145592
VL - 10
SP - 5373
EP - 5376
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -