Issue 4, 2011
From the journal:

Organic & Biomolecular Chemistry

Syntheses and reactivities of non-symmetrical “active ester” bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group†

Md. Chanmiya Sheikh,*a   Shunsuke Takagi,a   Mebumi Sakai,a   Tasuya Mori,a   Naoto Hayashi,b   Tetsuo Fujie,a   Shin Ono,a   Toshiaki Yoshimura*a  and  Hiroyuki Morita*a  

* Corresponding authors

a Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
E-mail: chansheikh@yahoo.com
Fax: +81-76-445-6850
Tel: +81-76-445-6850

b Department of Chemistry, Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan

Abstract

We have newly synthesized the non-symmetrical “phthalimidoyl active ester” bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazole group (i.e., 9, 15, and 16) on the basis of the reactivity study of the “active ester” model compounds, 11–14, toward the various nucleophiles and examined their reaction selectivity towards the same nucleophiles. Then, we applied for the modification of cholesterol at the more reactive site of the bi-dentate linkers to give 3β-cholesteryl 4-(phthalimidoyloxycarbonyl)butyrate (39), and the subsequent reaction of 39 with several amines, such as benzylamine, 4-chlorobenzylamine, 2-phenylethylamine, L-phenylalanine methyl ester, or diphenylalanine benzyl ester as a protein model of the cholesterol antigen.

Graphical abstract: Syntheses and reactivities of non-symmetrical “active ester” bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0OB00671H
Article type
Paper
Submitted
04 Sep 2010
Accepted
02 Nov 2010
First published
04 Jan 2011

Org. Biomol. Chem., 2011,9, 1244-1254

Permissions

Request permissions

Syntheses and reactivities of non-symmetrical “active ester” bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group

Md. C. Sheikh, S. Takagi, M. Sakai, T. Mori, N. Hayashi, T. Fujie, S. Ono, T. Yoshimura and H. Morita, Org. Biomol. Chem., 2011, 9, 1244 DOI: 10.1039/C0OB00671H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements