Practical synthesis of novel phosphonopeptides containing Aib(P)

Practical and convenient method for the synthesis of novel phosphonopeptides 8a-h and 10a-f incorporating the quaternary α-aminophosphonate 6 is reported. The target compounds were prepared in moderate to good yield based on the preparation of the quaternary α-aminophosphonate 6 followed by the form...

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Bibliographic Details
Published in:Journal of peptide science 2016-02, Vol.22 (2), p.70-75
Main Authors: Cervera-Villanueva, Juan Manuel Junior, Viveros-Ceballos, José Luis, Linzaga-Elizalde, Irma, Ordóñez, Mario
Format: Article
Language:English
Subjects:
Acylation
Aminoisobutyric Acids - chemistry
Catalysis
Formates - chemistry
Glycopeptides - chemical synthesis
Hydrogenation
Hydrolysis
Organophosphonates - chemical synthesis
Solvents - chemistry
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Summary:Practical and convenient method for the synthesis of novel phosphonopeptides 8a-h and 10a-f incorporating the quaternary α-aminophosphonate 6 is reported. The target compounds were prepared in moderate to good yield based on the preparation of the quaternary α-aminophosphonate 6 followed by the formation of the α-bromoamide 7 and subsequent nucleophilic substitution reaction with several amines or by peptide bond formation with several amino acids and with the quaternary α-aminophosphonate 6, using isobutyl chloroformate as activating agent under racemization-free condition.
ISSN:1099-1387
DOI:10.1002/psc.2841