Selective monoacylation of alkane-α,ω-diols using crude acetone powders of animal tissues

Ryszard Ostaszewski 1Dominik Koszelewski 1Marta Komar 1Adam Redzej 1Piotr Kiełbasiński 2

1. Polish Academy of Science, Institute of Organic Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
2. Polish Academy of Sciences, Center of Molecular and Macromolecular Studies (CMMS-PAS), Sienkiewicza 112, Łódź 90-363, Poland


Monofunctionalization of symmetrical substrates bearing two identical substituents continues to be a real challenge for organic chemists, despite a number of attempts that have been described in the literature [1]. Of particular importance is the monoacylation of polymethylene α,ω-diols, since the resulting products are crucial building blocks in the synthesis of various biologically active derivatives, e.g. insect sex pheromones [2].

In this paper a new methodology of the monoacylation of alkane-α,ω-diols will be presented, which rests upon the use of crude animal tissues (liver or kidney) acetone powders as the source of ester-forming enzymes.Clipboard.jpg

The reaction was performed in various solvents using isopropenyl acetate as the acetylating agent. It should be stressed, that certain crude acetone powders proved superior to a variety of commercially available enzymes. For example, the use of bovine liver acetone powder (BLAP) in the acetylation of octane-1,8-diol in toluene allowed to reach the 87% conversion with a monoacetylation excess of 95%. The influence of the solvents and reaction conditions on the reaction outcome will be discussed and experimental details will be presented.


This work was supported by the network "Synthesis, Structure and Therapeutic Properties of Compounds and Organic Substances".

[1] V. Framis, F. Camps, P. Clapes, Tetrahedron Lett. 2004, 45, 5031-5033 and references therein.
[2] H. Shargi, M. H. Sarvari, Tetrahedron 2003, 59, 3627-3633.


    Legal notice
    • Legal notice:

      Copyright (c) Pielaszek Research, all rights reserved.
      The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
      In every case, proper references including Author(s) name(s) and URL of this webpage: must be provided.


    Related papers
    1. Studies towards stereoselective bionanocatalysis on gold nanoparticles
    2. Studies toward Novel Peptidomimetc Inhibitors of Thioredoxin-Thiredoxin Reductase System
    3. Synthesis of marker compounds for detailed explanation the mechanism of anticancer activity of peptidomimetics with β-acyloxymethacrylic fragment
    4. Synthesis and biological evaluation of new inhibitors of thioredoxin - thioredoxin reductase.
    5. Chemoenzymatic approach to the synthesis of bioactive tripeptide mimetics for treatment of cancer
    6. Synthesis of novel, thioredoxin - thioredoxin reductase inhibitors
    7. Synthesis of novel, peptidic kinase inhibitors with cytotoxic activity
    8. First attempts at the enzyme-promoted hydrolysis of N-acyl phosphonoamides

    Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Adam Redzej
    See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

    Submitted: 2008-03-13 13:00
    Revised:   2009-06-07 00:48