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

19 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

Access to Document

10.1016/j.tet.2014.05.091

Cite this

@article{68618c37268c4226a1d4175473e47457,

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",

note = "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: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2014",

month = oct,

day = "21",

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

language = "English",

volume = "70",

pages = "7746--7752",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "42",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84907931503&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907931503&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.05.091

DO - 10.1016/j.tet.2014.05.091

M3 - Article

AN - SCOPUS:84907931503

VL - 70

SP - 7746

EP - 7752

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 42

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this