Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity

Qingzhou Zhang; Fan Jiang; Bingchuan Zhao; Huacan Lin; Yuan Tian; Mingsheng Xie; Guoyun Bai; Adam M. Gilbert; Gilles H. Goetz; Spiros Liras; Alan A. Mathiowetz; David A. Price; Kun Song; Meihua Tu; Yujie Wu; Tao Wang; Mark E. Flanagan; Yun Dong Wu; Zigang Li

doi:10.1038/srep38573

Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity

Qingzhou Zhang, Fan Jiang, Bingchuan Zhao, Huacan Lin, Yuan Tian, Mingsheng Xie, Guoyun Bai, Adam M. Gilbert, Gilles H. Goetz, Spiros Liras, Alan A. Mathiowetz, David A. Price, Kun Song, Meihua Tu, Yujie Wu, Tao Wang, Mark E. Flanagan, Yun Dong Wu, Zigang Li^*

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

Inducing α-helicity through side-chain cross-linking is a strategy that has been pursued to improve peptide conformational rigidity and bio-availability. Here we describe the preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings. Furthermore, a study of structure-activity relationships (SARs) disclosed properties with respect to ring size, sulfur position, oxidation state, and stereochemistry that show a propensity to induce α-helicity. Supporting data include circular dichroism spectroscopy (CD), NMR spectroscopy, and a single crystal X-ray structure for one such stabilized peptide. Finally, theoretical studies are presented to elucidate the effect of chiral sulfoxides in inducing backbone α-helicity.

Original language	English
Article number	38573
Journal	Scientific Reports
Volume	6
DOIs	https://doi.org/10.1038/srep38573
Publication status	Published - 9 Dec 2016
Externally published	Yes

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© 2016 The Author(s).

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title = "Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity",

abstract = "Inducing α-helicity through side-chain cross-linking is a strategy that has been pursued to improve peptide conformational rigidity and bio-availability. Here we describe the preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings. Furthermore, a study of structure-activity relationships (SARs) disclosed properties with respect to ring size, sulfur position, oxidation state, and stereochemistry that show a propensity to induce α-helicity. Supporting data include circular dichroism spectroscopy (CD), NMR spectroscopy, and a single crystal X-ray structure for one such stabilized peptide. Finally, theoretical studies are presented to elucidate the effect of chiral sulfoxides in inducing backbone α-helicity.",

author = "Qingzhou Zhang and Fan Jiang and Bingchuan Zhao and Huacan Lin and Yuan Tian and Mingsheng Xie and Guoyun Bai and Gilbert, \{Adam M.\} and Goetz, \{Gilles H.\} and Spiros Liras and Mathiowetz, \{Alan A.\} and Price, \{David A.\} and Kun Song and Meihua Tu and Yujie Wu and Tao Wang and Flanagan, \{Mark E.\} and Wu, \{Yun Dong\} and Zigang Li",

note = "Publisher Copyright: {\textcopyright} 2016 The Author(s).",

year = "2016",

month = dec,

day = "9",

doi = "10.1038/srep38573",

language = "English",

volume = "6",

journal = "Scientific Reports",

issn = "2045-2322",

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TY - JOUR

T1 - Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity

AU - Zhang, Qingzhou

AU - Jiang, Fan

AU - Zhao, Bingchuan

AU - Lin, Huacan

AU - Tian, Yuan

AU - Xie, Mingsheng

AU - Bai, Guoyun

AU - Gilbert, Adam M.

AU - Goetz, Gilles H.

AU - Liras, Spiros

AU - Mathiowetz, Alan A.

AU - Price, David A.

AU - Song, Kun

AU - Tu, Meihua

AU - Wu, Yujie

AU - Wang, Tao

AU - Flanagan, Mark E.

AU - Wu, Yun Dong

AU - Li, Zigang

PY - 2016/12/9

Y1 - 2016/12/9

N2 - Inducing α-helicity through side-chain cross-linking is a strategy that has been pursued to improve peptide conformational rigidity and bio-availability. Here we describe the preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings. Furthermore, a study of structure-activity relationships (SARs) disclosed properties with respect to ring size, sulfur position, oxidation state, and stereochemistry that show a propensity to induce α-helicity. Supporting data include circular dichroism spectroscopy (CD), NMR spectroscopy, and a single crystal X-ray structure for one such stabilized peptide. Finally, theoretical studies are presented to elucidate the effect of chiral sulfoxides in inducing backbone α-helicity.

AB - Inducing α-helicity through side-chain cross-linking is a strategy that has been pursued to improve peptide conformational rigidity and bio-availability. Here we describe the preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings. Furthermore, a study of structure-activity relationships (SARs) disclosed properties with respect to ring size, sulfur position, oxidation state, and stereochemistry that show a propensity to induce α-helicity. Supporting data include circular dichroism spectroscopy (CD), NMR spectroscopy, and a single crystal X-ray structure for one such stabilized peptide. Finally, theoretical studies are presented to elucidate the effect of chiral sulfoxides in inducing backbone α-helicity.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000389818900001

UR - https://www.scopus.com/pages/publications/85006040001

U2 - 10.1038/srep38573

DO - 10.1038/srep38573

M3 - Journal Article

C2 - 27934919

SN - 2045-2322

VL - 6

JO - Scientific Reports

JF - Scientific Reports

M1 - 38573

ER -

Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity

Abstract

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