Preparation of Pseudo‐Peptide Building Blocks with retro‐Thioamide Bond Mediated via Thiocarbamoyl Meldrum's Acid |
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| Authors: | Karolina Janikowska Sławomir Makowiec Janusz Rachoń |
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| Institution: | 1. Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, PL‐80‐952 Gdansk, (phone: +48?58?3471724;2. fax: +48?58?3472694) |
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| Abstract: | An easy and efficient synthesis of pseudo‐tripeptide containing a thiomalonamide moiety was developed. Isothiocyanate derivatives of amino acids react smoothly with 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione (Meldrum's acid) to yield new thiocarbamoyl derivatives of Meldrum's acids. Thermal decomposition of these new derivatives leads to thiocarbamoyl ketenes, which acylate amino acid esters to give pseudo‐tripeptides. |
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| Keywords: | Amides Peptides Acylation Ketenes Meldrum's acid |
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