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Synthesis 2017; 49(22): 5039-5044
DOI: 10.1055/s-0036-1588505
DOI: 10.1055/s-0036-1588505
paper
A Short and Scalable Synthesis of Orthogonally Protected Bis(aminomethyl)malonic Acid: Access to Bioactive Macrocyclic Peptides
Further Information
Publication History
Received: 28 April 2017
Accepted after revision: 27 June 2017
Publication Date:
01 August 2017 (online)
Abstract
A short and scalable process for the preparation of multi-gram quantities of orthogonally protected bis(aminomethyl)malonic acid in good yield from readily available starting material is described. These orthogonally protected amino acids are important building blocks to make peptides based drugs, glycoconjugates, and in the total synthesis of peptide natural products. The newly developed route has only six steps with an overall yield of 27%, which involves nucleophilic attack of a malonate on an imide as one of the key steps.
Key words
macrocyclic peptides - orthogonally protected amino acid - gram scale synthesis - improved process - benzyl ethyl malonateSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588505.
- Supporting Information
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