Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction

Jeong Kyu Bang; Hiromi Naka; Kenta Teruya; Saburo Aimoto; Hiroyuki Konno; Kazuto Nosaka; Tadashi Tatsumi; Kenichi Akaji

doi:10.1021/jo051872s

Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction

Jeong Kyu Bang, Hiromi Naka, Kenta Teruya, Saburo Aimoto, Hiroyuki Konno, Kazuto Nosaka, Tadashi Tatsumi, Kenichi Akaji

MED - United Centers for Advanced Research and Translational Medicine (ART)

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

10 Citations (Scopus)

Abstract

The solid-phase Horner-Emmons reaction was successfully applied for the convenient syntheses of olefin-containing protease inhibitors. The isomerization during the solid-phase Horner-Emmons reaction can be minimized simply by the use of an appropriate amount of the base. The synthesized olefin peptides, which have an olefin γ-amino acid at the scissile site, were found to act as effective inhibitors for the HTLV-1 protease for the first time.

Original language	English
Pages (from-to)	10596-10599
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	25
DOIs	https://doi.org/10.1021/jo051872s
Publication status	Published - 2005 Dec 9

Access to Document

10.1021/jo051872s

Cite this

@article{9ec618fc34bd4029ba611545deea03ab,

title = "Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction",

abstract = "The solid-phase Horner-Emmons reaction was successfully applied for the convenient syntheses of olefin-containing protease inhibitors. The isomerization during the solid-phase Horner-Emmons reaction can be minimized simply by the use of an appropriate amount of the base. The synthesized olefin peptides, which have an olefin γ-amino acid at the scissile site, were found to act as effective inhibitors for the HTLV-1 protease for the first time.",

author = "Bang, {Jeong Kyu} and Hiromi Naka and Kenta Teruya and Saburo Aimoto and Hiroyuki Konno and Kazuto Nosaka and Tadashi Tatsumi and Kenichi Akaji",

year = "2005",

month = dec,

day = "9",

doi = "10.1021/jo051872s",

language = "English",

volume = "70",

pages = "10596--10599",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction

AU - Bang, Jeong Kyu

AU - Naka, Hiromi

AU - Teruya, Kenta

AU - Aimoto, Saburo

AU - Konno, Hiroyuki

AU - Nosaka, Kazuto

AU - Tatsumi, Tadashi

AU - Akaji, Kenichi

PY - 2005/12/9

Y1 - 2005/12/9

N2 - The solid-phase Horner-Emmons reaction was successfully applied for the convenient syntheses of olefin-containing protease inhibitors. The isomerization during the solid-phase Horner-Emmons reaction can be minimized simply by the use of an appropriate amount of the base. The synthesized olefin peptides, which have an olefin γ-amino acid at the scissile site, were found to act as effective inhibitors for the HTLV-1 protease for the first time.

AB - The solid-phase Horner-Emmons reaction was successfully applied for the convenient syntheses of olefin-containing protease inhibitors. The isomerization during the solid-phase Horner-Emmons reaction can be minimized simply by the use of an appropriate amount of the base. The synthesized olefin peptides, which have an olefin γ-amino acid at the scissile site, were found to act as effective inhibitors for the HTLV-1 protease for the first time.

UR - http://www.scopus.com/inward/record.url?scp=28744436883&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=28744436883&partnerID=8YFLogxK

U2 - 10.1021/jo051872s

DO - 10.1021/jo051872s

M3 - Article

C2 - 16323881

AN - SCOPUS:28744436883

SN - 0022-3263

VL - 70

SP - 10596

EP - 10599

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction

Abstract

Access to Document

Other files and links

Fingerprint

Cite this