Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation

Tomoya Yamashita; Hiroaki Matoba; Takefumi Kuranaga; Masayuki Inoue

doi:10.1016/j.tet.2014.05.091

Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation

Tomoya Yamashita, Hiroaki Matoba, Takefumi Kuranaga, Masayuki Inoue

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

21 Citations (Scopus)

Abstract

Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.

Original language	English
Pages (from-to)	7746-7752
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2014.05.091
Publication status	Published - 2014 Oct 21
Externally published	Yes

Keywords

Peptides
Solid-phase synthesis
Staudinger ligation
Total synthesis
TRPV1 antagonist

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.05.091

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title = "Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation",

abstract = "Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.",

keywords = "Peptides, Solid-phase synthesis, Staudinger ligation, Total synthesis, TRPV1 antagonist",

author = "Tomoya Yamashita and Hiroaki Matoba and Takefumi Kuranaga and Masayuki Inoue",

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doi = "10.1016/j.tet.2014.05.091",

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T1 - Total syntheses of nobilamides B and D

T2 - Application of traceless Staudinger ligation

AU - Yamashita, Tomoya

AU - Matoba, Hiroaki

AU - Kuranaga, Takefumi

AU - Inoue, Masayuki

N1 - Funding Information: This work was supported financially by Funding Program for Next Generation World-Leading Researchers [ Japan Society for the Promotion of Science (JSPS)] to M.I. and a Grant-in-Aid for Young Scientists (B) (JSPS) to T.K. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/10/21

Y1 - 2014/10/21

N2 - Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.

AB - Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.

KW - Peptides

KW - Solid-phase synthesis

KW - Staudinger ligation

KW - Total synthesis

KW - TRPV1 antagonist

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JF - Tetrahedron

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Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation

Abstract

Keywords

ASJC Scopus subject areas

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