Chemie von α-Aminonitrilen. Aziridin-2-carbonitril, ein Vorläufer von rca-O3-Phosphoserinnitril und Glycolaldehyd-phosphat
| Autor: | Yi-Bin Xiang, Ernst Wagner, Karl Baumann, Jürgen Gück, Albert Eschenmoser |
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| Rok vydání: | 1990 |
| Předmět: |
chemistry.chemical_classification
Sugar phosphates Aqueous solution Stereochemistry Organic Chemistry Regioselectivity Biochemistry Medicinal chemistry Catalysis Inorganic Chemistry Turn (biochemistry) chemistry Drug Discovery Glycolaldehyde phosphate Physical and Theoretical Chemistry Aliphatic compound |
| Zdroj: | Helvetica Chimica Acta. 73:1391-1409 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.19900730525 |
| Popis: | Chemistry of α-Aminonitriles. Aziridine-2-carbonitrile, a Source of Racemic O′-Phosphoserinenitrile and Glycolaldehyde Phosphate Racemic aziridine-2-carbonitrile (rac-1) in MeCN solution reacts regioselectively (> 90%) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic O3-tosylserinenitrile (rac-2) via β-ring opening (Scheme 2). A similar regioselective reaction takes place between rac-l and H3PO4 to produce racemic O3-phosphoserinenitrite (rac-3) which is in turn a source of glycolaldehyde phosphate (=formylmethyl dihydrogenphosphate) under the conditions of a ‘retro-Strecker’ reaction in aqueous solution (Scheme 6). These experiments document a close structural relationship between the simplest of the sugar phosphates and an α-aminonitrile precursor. The English Footnotes (*) referring to Schemes 1-7 are intended to provide an extension of this summary. |
| Databáze: | OpenAIRE |
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