Chemoenzymatic Synthesis of Racemic and Enantiomerically Pure Phosphaaspartic Acid and Phosphaarginine
| Autor: | Renzhe Qian, Friedrich Hammerschmidt, Elena Macoratti, Edyta Kuliszewska |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Thermomyces lanuginosus biology Double bond 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry 010402 general chemistry 01 natural sciences Chloride Chiral resolution 0104 chemical sciences Enzyme catalysis Hydroboration Group (periodic table) biology.protein medicine Organic chemistry Physical and Theoretical Chemistry Lipase medicine.drug |
| Zdroj: | European Journal of Organic Chemistry. 2017:4836-4845 |
| ISSN: | 1434-193X |
| Popis: | Diisopropyl allyloxymethylphosphonate prepared by a one-pot procedure was isomerized to give racemic 1-hydroxy-3-butenylphosphonate with LDA by a [2,3]-sigmatropic rearrangement. Chloroacetylation delivered an ester, which was resolved in a two-phase system by using the lipase from Thermomyces lanuginosus. Racemic and (S)-α-hydroxyphosphonate 6 were converted to (±)- and (R)-phosphaaspartic acid by functional-group manipulation. (±)-, (R)- and (S)-6 were first esterified with 4-nitrobenzenesulfonyl chloride before hydroboration to transform the double bond into a hydroxyethyl group. The hydroxyl group was manipulated to give a guanidinyl group and the 4-nitrobenzenesulfonyloxy to give an amino group. Global deprotection of the α-aminophosphonates yielded the desired phosphaamino acids. |
| Databáze: | OpenAIRE |
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