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Une nouvelle méthode de synthèse peptidique
Abstract
En ajoutant à un acide aminé ou peptide N‐acylé dans un solvant organique une amine tertiaire (tri‐n‐butylamine), puis du chloroformiate ( = chlorocarbonate = chlorométhanoate) d'éthyle (ou de méthyle) en quantités équimoléculaires, on obtient immédiatement une solution contenant des anhydrides mixtes de la forme: magnified image Si, à une telle solution, on ajoute une solution aqueuse ou organique d'un acide aminé, d'un peptide, d'un ester de ceux‐ci, ou d'une amine, on obtient sur le champ la formation d'une liaison peptidique, avec dégagement de CO 2. Grâce à cette méthode simple et rapide, nous avons préparé divers dipeptides ainsi qu'un tétrapeptide (à partir de deux dipeptides). Avec l'ammoniac, ces anhydrides mixtes alcoylcarboniques donnent des amides.
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Citations
Cited by
Peptide Coupling Reagents, More than a Letter Soup
El-Faham, A., & Albericio, F. (2011) · Chemical Reviews · doi:10.1021/cr100048w · Cited by 1,245
Heterolytic Fragmentation. A Class of Organic Reactions
Grob, C. A., & Schiess, P. W. (1967) · Angewandte Chemie International Edition in English · doi:10.1002/anie.196700011 · Cited by 354
The incorporation of amines into protein
Clarke, D. D., Mycek, M. J., Neidle, A., & Waelsch, H. (1959) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(59)90413-8 · Cited by 272
Chloroformates in gas chromatography as general purpose derivatizing agents
Hušek, P. (1998) · Journal of Chromatography B: Biomedical Sciences and Applications · doi:10.1016/s0378-4347(98)00136-4 · Cited by 268
The Formation of Peptide Bonds:A General Survey
JONES, J. H. (1979) · Major Methods of Peptide Bond Formation · doi:10.1016/b978-0-12-304201-9.50008-4 · Cited by 9
Metadata
- Authors
- Boissonnas, R. A.
- Venue
- Helvetica Chimica Acta
- Publisher
- Wiley
- Published
- 1951-01
- Volume
- 34
- Issue
- 3
- Pages
- 874-879
- ISSN
- 0018-019X (ISSN-L)
- 1522-2675
- OpenAlex
- W2113946213
- Cited by
- 390
- References
- 0
- FWCI
- 8.23
- Type
- journal article
- Language
- en
- Open access
- closed
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- Boissonnas, R. A. (1951). Une nouvelle méthode de synthèse peptidique. Helvetica Chimica Acta. https://doi.org/10.1002/hlca.19510340318
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