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Synthesis 2015; 47(10): 1479-1487
DOI: 10.1055/s-0034-1380267
DOI: 10.1055/s-0034-1380267
paper
Convergent and Facile Synthesis of Hybrid Sulfonophosphonodipeptides
Autor*innen
Weitere Informationen
Publikationsverlauf
Received: 29. Dezember 2014
Accepted after revision: 01. Februar 2015
Publikationsdatum:
02. März 2015 (online)
Abstract
A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.
Key words
hybrid peptide - hydrolysis - Mannich reaction - phosphonopeptide - sulfonamide - sulfonopeptideSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380267.
Copies of 1H NMR, 13C NMR, and 31P NMR spectra of the products 3, and 31P NMR spectra of the mechanism tracing experiments are included.
- Supporting Information (PDF) (opens in new window)
-
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