Peptidomimicry with C                         2                         -symmetric oligourea derivatives of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane: Chirality and chain length-dependent conformation

Pengyun Yue; Siqing Peng; Sean Parkin; Tonglei Li; Faquan Yu; Sihui Long

doi:10.1002/slct.201801900

Peptidomimicry with C ₂ -symmetric oligourea derivatives of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane: Chirality and chain length-dependent conformation

Pengyun Yue
, Siqing Peng
, Sean Parkin
, Tonglei Li
, Faquan Yu
, Sihui Long

Chemistry

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

Abstract

To study whether C ₂ symmetric oligoureas form secondary structures such as sheets and helices/turns to serve as peptidomimetics, conformations of oligoureas composed of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane were investigated using X-ray diffraction, UV, CD and NMR spectroscopic methods. Alternating heterochiral diamines in these chains strongly favored helical conformations. The conformations of C ₂ -symmetric chains of homochiral diamines were more conditional, giving indications of conditional extended and helical structure.

Original language	English
Pages (from-to)	11035-11041
Number of pages	7
Journal	ChemistrySelect
Volume	3
Issue number	39
DOIs	https://doi.org/10.1002/slct.201801900
State	Published - Oct 24 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Funding

SL is grateful to National Science Foundation of Hubei Province for financial support (2014CFB787), and thanks Dr. Arthur Cammers for helpful discussions. Crystallography at UK is supported by the NSF MRI program (CHE-0319176 and CHE-1625732).

Funders	Funder number
National Science Foundation (NSF)	CHE-0319176, CHE-1625732

Keywords

C symmetric
Conformation
Oligourea
Peptidomimetic
Secondary structure

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/slct.201801900

Cite this

@article{ce31c7d9a1b141cd93c6b0c0aac29137,

title = "Peptidomimicry with C 2 -symmetric oligourea derivatives of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane: Chirality and chain length-dependent conformation",

abstract = " To study whether C 2 symmetric oligoureas form secondary structures such as sheets and helices/turns to serve as peptidomimetics, conformations of oligoureas composed of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane were investigated using X-ray diffraction, UV, CD and NMR spectroscopic methods. Alternating heterochiral diamines in these chains strongly favored helical conformations. The conformations of C 2 -symmetric chains of homochiral diamines were more conditional, giving indications of conditional extended and helical structure.",

keywords = "C symmetric, Conformation, Oligourea, Peptidomimetic, Secondary structure",

author = "Pengyun Yue and Siqing Peng and Sean Parkin and Tonglei Li and Faquan Yu and Sihui Long",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2018",

month = oct,

day = "24",

doi = "10.1002/slct.201801900",

language = "English",

volume = "3",

pages = "11035--11041",

number = "39",

}

Peptidomimicry with C ₂ -symmetric oligourea derivatives of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane: Chirality and chain length-dependent conformation. / Yue, Pengyun; Peng, Siqing; Parkin, Sean et al.
In: ChemistrySelect, Vol. 3, No. 39, 24.10.2018, p. 11035-11041.

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

TY - JOUR

T1 - Peptidomimicry with C 2 -symmetric oligourea derivatives of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane

T2 - Chirality and chain length-dependent conformation

AU - Yue, Pengyun

AU - Peng, Siqing

AU - Parkin, Sean

AU - Li, Tonglei

AU - Yu, Faquan

AU - Long, Sihui

PY - 2018/10/24

Y1 - 2018/10/24

N2 - To study whether C 2 symmetric oligoureas form secondary structures such as sheets and helices/turns to serve as peptidomimetics, conformations of oligoureas composed of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane were investigated using X-ray diffraction, UV, CD and NMR spectroscopic methods. Alternating heterochiral diamines in these chains strongly favored helical conformations. The conformations of C 2 -symmetric chains of homochiral diamines were more conditional, giving indications of conditional extended and helical structure.

AB - To study whether C 2 symmetric oligoureas form secondary structures such as sheets and helices/turns to serve as peptidomimetics, conformations of oligoureas composed of 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-diaminoethane were investigated using X-ray diffraction, UV, CD and NMR spectroscopic methods. Alternating heterochiral diamines in these chains strongly favored helical conformations. The conformations of C 2 -symmetric chains of homochiral diamines were more conditional, giving indications of conditional extended and helical structure.

KW - C symmetric

KW - Conformation

KW - Oligourea

KW - Peptidomimetic

KW - Secondary structure

UR - https://www.scopus.com/pages/publications/85062610184

UR - https://www.scopus.com/pages/publications/85062610184#tab=citedBy

U2 - 10.1002/slct.201801900

DO - 10.1002/slct.201801900

M3 - Article

AN - SCOPUS:85062610184

VL - 3

SP - 11035

EP - 11041

JO - ChemistrySelect

JF - ChemistrySelect

IS - 39

ER -