Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids

Bong Hyeon Baek, Myung Ryul Lee, Kwang Yon Kim, Ung In Cho, Doo Wan Boo, Injae Shin

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The folded structures of peptidomimetics containing dimers of oxanipecotic acid (Oxa) in loop segments were characterized and compared with those of the corresponding nipecotic acid (Nip)-based ones. According to structural studies using FT-IR and NMR spectroscopies, di-oxanipecotic acid adopted more stable turn conformations than di-nipecotic acid, and for tetramers, L,(S)-Oxa,(S)-Oxa,L and L,(S)-Oxa,(R)-Oxa,L formed hairpin-like structures but only L,(R)-Nip,(S)-Nip,L promoted the stable folded conformations.

Original languageEnglish
Pages (from-to)3447-3450
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number17
DOIs
Publication statusPublished - 2003 Apr 21

Fingerprint

Nipecotic Acids
Acids
Conformations
Peptidomimetics
Dimers
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Baek, Bong Hyeon ; Lee, Myung Ryul ; Kim, Kwang Yon ; Cho, Ung In ; Boo, Doo Wan ; Shin, Injae. / Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 17. pp. 3447-3450.
@article{f14098b684014fe99aeecd9cab23cffd,
title = "Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids",
abstract = "The folded structures of peptidomimetics containing dimers of oxanipecotic acid (Oxa) in loop segments were characterized and compared with those of the corresponding nipecotic acid (Nip)-based ones. According to structural studies using FT-IR and NMR spectroscopies, di-oxanipecotic acid adopted more stable turn conformations than di-nipecotic acid, and for tetramers, L,(S)-Oxa,(S)-Oxa,L and L,(S)-Oxa,(R)-Oxa,L formed hairpin-like structures but only L,(R)-Nip,(S)-Nip,L promoted the stable folded conformations.",
author = "Baek, {Bong Hyeon} and Lee, {Myung Ryul} and Kim, {Kwang Yon} and Cho, {Ung In} and Boo, {Doo Wan} and Injae Shin",
year = "2003",
month = "4",
day = "21",
doi = "10.1016/S0040-4039(03)00677-4",
language = "English",
volume = "44",
pages = "3447--3450",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "17",

}

Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids. / Baek, Bong Hyeon; Lee, Myung Ryul; Kim, Kwang Yon; Cho, Ung In; Boo, Doo Wan; Shin, Injae.

In: Tetrahedron Letters, Vol. 44, No. 17, 21.04.2003, p. 3447-3450.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids

AU - Baek, Bong Hyeon

AU - Lee, Myung Ryul

AU - Kim, Kwang Yon

AU - Cho, Ung In

AU - Boo, Doo Wan

AU - Shin, Injae

PY - 2003/4/21

Y1 - 2003/4/21

N2 - The folded structures of peptidomimetics containing dimers of oxanipecotic acid (Oxa) in loop segments were characterized and compared with those of the corresponding nipecotic acid (Nip)-based ones. According to structural studies using FT-IR and NMR spectroscopies, di-oxanipecotic acid adopted more stable turn conformations than di-nipecotic acid, and for tetramers, L,(S)-Oxa,(S)-Oxa,L and L,(S)-Oxa,(R)-Oxa,L formed hairpin-like structures but only L,(R)-Nip,(S)-Nip,L promoted the stable folded conformations.

AB - The folded structures of peptidomimetics containing dimers of oxanipecotic acid (Oxa) in loop segments were characterized and compared with those of the corresponding nipecotic acid (Nip)-based ones. According to structural studies using FT-IR and NMR spectroscopies, di-oxanipecotic acid adopted more stable turn conformations than di-nipecotic acid, and for tetramers, L,(S)-Oxa,(S)-Oxa,L and L,(S)-Oxa,(R)-Oxa,L formed hairpin-like structures but only L,(R)-Nip,(S)-Nip,L promoted the stable folded conformations.

UR - http://www.scopus.com/inward/record.url?scp=0037459869&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037459869&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(03)00677-4

DO - 10.1016/S0040-4039(03)00677-4

M3 - Article

VL - 44

SP - 3447

EP - 3450

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -