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

doi:10.1016/S0040-4039(03)00677-4

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

Department of Chemistry

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

6 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 language	English
Pages (from-to)	3447-3450
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(03)00677-4
Publication status	Published - 2003 Apr 21

Bibliographical note

Funding Information:
This work was supported by a grant of the Center for Integrated Molecular Systems (KOSEF). We thank Dr. Yong Jun Chung for several helpful discussions concerning IR studies.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(03)00677-4

Cite this

@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",

note = "Funding Information: This work was supported by a grant of the Center for Integrated Molecular Systems (KOSEF). We thank Dr. Yong Jun Chung for several helpful discussions concerning IR studies.",

year = "2003",

month = apr,

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",

}

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

N1 - Funding Information: This work was supported by a grant of the Center for Integrated Molecular Systems (KOSEF). We thank Dr. Yong Jun Chung for several helpful discussions concerning IR studies.

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

AN - SCOPUS:0037459869

SN - 0040-4039

VL - 44

SP - 3447

EP - 3450

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this