Issue 0, 1984

1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids

Abstract

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described. These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrqsine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved. Tha alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties. Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkyl-phosphonic acid analogues of (±)-alanine, (–)-alanine, (±)-valine, (–)-valine, (±)-serine, (±)-threonine, (±)-lysine, (–)-leucine, and (±)-ornithine.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2845-2853

1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids

E. K. Baylis, C. D. Campbell and J. G. Dingwall, J. Chem. Soc., Perkin Trans. 1, 1984, 2845 DOI: 10.1039/P19840002845

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.

Spotlight

Advertisements