A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid
| Autor: | Horst Kessler, Christoph Riemer, Tom Bayer |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Cystine Antineoplastic Agents Octreotide Biochemistry High-performance liquid chromatography Peptides Cyclic chemistry.chemical_compound Glutamates Structural Biology Drug Discovery Molecular Biology Racemization Chromatography High Pressure Liquid Pharmacology Chemistry Organic Chemistry Diastereomer General Medicine Nuclear magnetic resonance spectroscopy Hormones Models Chemical Molecular Medicine Amine gas treating Gas chromatography Peptides Somatostatin Derivative (chemistry) |
| Zdroj: | Journal of peptide science : an official publication of the European Peptide Society. 7(5) |
| ISSN: | 1075-2617 |
| Popis: | A new synthesis of orthogonally protected diaminoglutaric acid containing peptides using the Ugi four component condensation is presented. To demonstrate that this method is useful to replace cystine by diaminoglutaric acid in biologically interesting peptides, we built up two cyclic somatostatin analogues deriving from Sandostatin and from TT-232. A photolytically cleavable amine derivative of the nitroveratryl type is used for the Ugi four component condensation. Because of a racemic build up of the new stereocentre of the diaminoglutaric acid, and racemization of the isonitrile component, four diastereomeric peptides resulted that were separated by HPLC. The stereochemistry of the cyclopeptides could be easily and unambiguously assigned by chiral gas chromatography and a reference sample of enantiomerically pure (2S,4S)-diaminoglutaric acid. |
| Databáze: | OpenAIRE |
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