Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

Masato Sasaki; Kazuo Tachibana

doi:10.1016/j.tetlet.2007.03.041

Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

Masato Sasaki, Kazuo Tachibana

LIF - Molecular and Chemical Life Science

The University of Tokyo

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

14 Citations (Scopus)

Abstract

Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between α-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the α-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins.

Original language	English
Pages (from-to)	3181-3186
Number of pages	6
Journal	Tetrahedron Letters
Volume	48
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.041
Publication status	Published - 2007 Apr 30

Keywords

α-Helix
Convergent synthesis
Polycyclic ether
Simplified ring system
Suzuki-Miyaura cross coupling

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10.1016/j.tetlet.2007.03.041

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@article{1a8f1b6ed31b41aeb741ebfffe8ee761,

title = "Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins",

abstract = "Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between α-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the α-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins.",

keywords = "α-Helix, Convergent synthesis, Polycyclic ether, Simplified ring system, Suzuki-Miyaura cross coupling",

author = "Masato Sasaki and Kazuo Tachibana",

note = "Funding Information: We are grateful to Professor M. Satake in our laboratory for a valuable discussion. Mr. S. Motoi contributed to this study in an earlier stage. This work was financially supported by CREST, Japan Science and Technology Agency (JST) and 21st century COE program. A fellowship (to M.S.) from the Ajinomoto Scholarship Foundation is also gratefully acknowledged.",

year = "2007",

month = apr,

day = "30",

doi = "10.1016/j.tetlet.2007.03.041",

language = "English",

volume = "48",

pages = "3181--3186",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

AU - Sasaki, Masato

AU - Tachibana, Kazuo

N1 - Funding Information: We are grateful to Professor M. Satake in our laboratory for a valuable discussion. Mr. S. Motoi contributed to this study in an earlier stage. This work was financially supported by CREST, Japan Science and Technology Agency (JST) and 21st century COE program. A fellowship (to M.S.) from the Ajinomoto Scholarship Foundation is also gratefully acknowledged.

PY - 2007/4/30

Y1 - 2007/4/30

N2 - Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between α-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the α-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins.

AB - Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between α-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the α-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins.

KW - α-Helix

KW - Convergent synthesis

KW - Polycyclic ether

KW - Simplified ring system

KW - Suzuki-Miyaura cross coupling

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U2 - 10.1016/j.tetlet.2007.03.041

DO - 10.1016/j.tetlet.2007.03.041

M3 - Article

AN - SCOPUS:34047140769

SN - 0040-4039

VL - 48

SP - 3181

EP - 3186

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

Abstract

Keywords

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