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.
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U2 - 10.1016/j.tet.2014.05.091
DO - 10.1016/j.tet.2014.05.091
M3 - Article
AN - SCOPUS:84907931503
SN - 0040-4020
VL - 70
SP - 7746
EP - 7752
JO - Tetrahedron
JF - Tetrahedron
IS - 42
ER -