4.8 Article

Cis-Trans Proline Isomerization Effects on Collagen Triple-Helix Stability Are Limited

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 38, 页码 13728-13732

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ja904177k

关键词

-

资金

  1. ACS-PRF [44314-AC7]
  2. NSF [CHE-0749061]

向作者/读者索取更多资源

We investigated the effect of restricting cis-trans proline isomerization on collagen triple-helix stability. The Pro residues at the Xaa and Yaa positions of an (Xaa-Yaa-Gly) triplet were replaced by a Pro-trans-Pro alkene isostere in the host-guest peptide, H-(Pro-Pro-Gly)(10)-OH. The resulting alkene isostere peptide had a T-m value 53.6 degrees C lower than that of the control peptide. The Pro-trans-Pro alkene isostere peptide had a T-m value 3.9 degrees C higher than that of the previously reported Pro-trans-Gly alkene isostere peptide that did not involve cis-trans Pro isomerization (Jenkins, C. L.; Vasbinder, M. M.; Miller, S. J.; Raines, R. T. Org. Lett. 2005, 7, 2619-22). Thus, single cis-trans proline amide isomerization alone has limited contribution to the overall stability of the collagen triple helix. Since collagen has a high content of imino acid residues, the cumulative effects of cis-trans isomerization may be quite significant. The peptide containing the Pro-trans-Pro isostere was significantly less stable than the previously reported Gly-trans-Pro alkene isostere peptide that retained the backbone interchain hydrogen bond (Dai, N.; Wang, X. J.; Etzkorn, F. A. J. Am. Chem. Soc. 2008, 130, 5396-5397), which confirms that direct interchain backbone hydrogen bonding is a major force for stabilizing the collagen triple helix.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Biochemistry & Molecular Biology

Chemical Tools To Decipher Regulation of Phosphatases by Proline Isomerization on Eukaryotic RNA Polymerase II

Joshua E. Mayfield, Shuang Fan, Shuo Wei, Mengmeng Zhang, Bing Li, Andrew D. Ellington, Felicia A. Etzkorn, Yan Jessie Zhang

ACS CHEMICAL BIOLOGY (2015)

Article Biochemistry & Molecular Biology

Stereospecific Phosphorylation by the Central Mitotic Kinase Cdk1-Cyclin B

Felicia A. Etzkorn, Song Zhao

ACS Chemical Biology (2015)

Article Multidisciplinary Sciences

Stereochemical Control in the Still-Wittig Rearrangement Synthesis of Cyclohexyl (Z)-Alkene Inhibitors of Pin1

Xingguo R. Chen, Shuang A. Fan, Rachel I. Ware, Felicia A. Etzkorn

PLOS ONE (2015)

Article Biochemistry & Molecular Biology

Structural and Kinetic Analysis of Prolyl-isomerization/Phosphorylation Cross-Talk in the CTD Code

Mengmeng Zhang, Xiaodong J. Wang, Xi Chen, Marianne E. Bowman, Yonghua Luo, Joseph P. Noel, Andrew D. Ellington, Felicia A. Etzkorn, Yan Zhang

ACS CHEMICAL BIOLOGY (2012)

Article Biochemistry & Molecular Biology

Kinetic Isotope Effects Support the Twisted Amide Mechanism of Pin1 Peptidyl-Prolyl Isomerase

Ana Y. Mercedes-Camacho, Ashley B. Mullins, Matthew D. Mason, Guoyan G. Xu, Brendan J. Mahoney, Xingsheng Wang, Jeffrey W. Peng, Felicia A. Etzkorn

BIOCHEMISTRY (2013)

Article Biochemistry & Molecular Biology

A Prolyl-Isomerase Mediates Dopamine-Dependent Plasticity and Cocaine Motor Sensitization

Joo Min Park, Jia-Hua Hu, Aleksandr Milshteyn, Ping-Wu Zhang, Chester G. Moore, Sungjin Park, Michael C. Datko, Racquel D. Domingo, Cindy M. Reyes, Xiaodong J. Wang, Felicia A. Etzkorn, Bo Xiao, Karen K. Szumlinski, Dorothee Kern, David J. Linden, Paul F. Worley

Article Environmental Sciences

Drinking water treatment is not associated with an observed increase in neural tube defects in mice

Vanessa E. Melin, David W. Johnstone, Felicia A. Etzkorn, Terry C. Hrubec

ENVIRONMENTAL MONITORING AND ASSESSMENT (2014)

Article Biochemistry & Molecular Biology

Regulation of CK2 by phosphorylation and O-GlcNAcylation revealed by semisynthesis

Mary Katherine Tarrant, Hee-Sool Rho, Zhi Xie, Yu Lin Jiang, Christopher Gross, Jeffrey C. Culhane, Gai Yan, Jiang Qian, Yoshitaka Ichikawa, Tatsuji Matsuoka, Natasha Zachara, Felicia A. Etzkorn, Gerald W. Hart, Jun Seop Jeong, Seth Blackshaw, Heng Zhu, Philip A. Cole

NATURE CHEMICAL BIOLOGY (2012)

Article Biochemistry & Molecular Biology

Evaluation of insect CAP(2b) analogs with either an (E)-alkene, trans- or a (Z)-alkene, cis-Pro isostere identifies the Pro orientation for antidiuretic activity in the stink bug

Ronald J. Nachman, Xiaodong J. Wang, Felicia A. Etzkorn, Krzysztof Kaczmarek, Janusz Zabrocki, Juan Lopez, Geoffrey M. Coast

PEPTIDES (2013)

Article Multidisciplinary Sciences

Cyclohexyl Ketone Inhibitors of Pin1 Dock in a Trans-Diaxial Cyclohexane Conformation

Guoyan G. Xu, Carla Slebodnick, Felicia A. Etzkorn

PLOS ONE (2012)

Article Multidisciplinary Sciences

Stereospecific gating of functional motions in Pin1

Andrew T. Namanja, Xiaodong J. Wang, Bailing Xu, Ana Y. Mercedes-Camacho, Kimberly A. Wilson, Felicia A. Etzkorn, Jeffrey W. Peng

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2011)

Article Chemistry, Physical

Conformational Analysis of n→π* Interactions in Collagen Triple Helix Models

Felicia A. Etzkorn, Rachel I. Ware, Amanda M. Pester, Diego Troya

JOURNAL OF PHYSICAL CHEMISTRY B (2019)

Article Biochemistry & Molecular Biology

Designed leucine-rich repeat proteins bind two muramyl dipeptide ligands

Christina S. Kim, Anne M. Brown, Tijana Z. Grove, Felicia A. Etzkorn

Summary: Novel consensus leucine-rich repeat proteins (CLRR4-8) based on the LRR domain of NOD-like receptors show promise in high-affinity binding to bacterial cell wall component MDP. The biphasic binding curves and docking studies suggest multi-MDP binding, indicating potential for future pathogen biosensor design.

PROTEIN SCIENCE (2021)

Article Chemistry, Physical

Conformational Analysis of Fluoro-, Chloro-, and Proteo-Alkene Gly-Pro and Pro-Pro Isosteres to Mimic Collagen

Paul J. Arcoria, Rachel Ware, Sunny Makwana, Diego Troya, Felicia A. Etzkorn

Summary: Fluoro- and chloro-alkene mimics of Gly-Pro and Pro-Pro can participate in n ->pi* donation to stabilize PPII conformations, but are poor n.p* acceptors. Proteo-alkene mimics lack significant n ->pi* interactions, leading to unstable PPII-like geometries.

JOURNAL OF PHYSICAL CHEMISTRY B (2022)

Article Chemistry, Multidisciplinary

Integrating Green Chemistry into Chemistry Education

Felicia A. A. Etzkorn, Jamie L. L. Ferguson

Summary: Full integration of green chemistry into undergraduate curriculum is essential for preparing students for a sustainable future. This article discusses the reasons for curriculum change, institutions leading the way in integration efforts, and available textbooks for both classroom and laboratory. The authors emphasize the need to give college professors more time to revamp the curriculum and to value their efforts. They call on the chemistry education community to participate in these efforts immediately.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

暂无数据