Issue 73, 2015
From the journal:

RSC Advances

An efficient one pot ipso-nitration: structural transformation of a dipeptide by N-terminus modification†

Rajib Sarkar,a   Krishnendu Majia  and  Debasish Haldar*a  

* Corresponding authors

a Department, of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal 741246, India
E-mail: deba_h76@yahoo.com, deba_h76@iiserkol.ac.in
Fax: +913325873020
Tel: +913325873119

Abstract

The one pot ipso-nitration of Boc-capped rigid dipeptide Boc-Maba-Aba-OMe 1 gave poor yields under excess NaNO2 in dilute mineral acidic medium at 0 °C. The yield is improved with the use of a catalytic amount of CuSO4. The N-terminus modification leads to structural transformation of the dipeptide from anti parallel to parallel β-sheet. We have also explored the reverse reaction by one pot reduction of nitro group to amine and Boc protection.

Graphical abstract: An efficient one pot ipso-nitration: structural transformation of a dipeptide by N-terminus modification

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Article information

DOI
https://doi.org/10.1039/C5RA09789D
Article type
Paper
Submitted
25 May 2015
Accepted
03 Jul 2015
First published
03 Jul 2015

RSC Adv., 2015,5, 59570-59575

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An efficient one pot ipso-nitration: structural transformation of a dipeptide by N-terminus modification

R. Sarkar, K. Maji and D. Haldar, RSC Adv., 2015, 5, 59570 DOI: 10.1039/C5RA09789D

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