Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids

A number of protected proline‐containing dipeptides Boc‐Xaa‐Pro‐OBut were converted via epimerization‐free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc‐Xaa‐Glp‐OBut. The latter were subjected to oxidative Hoffman‐type rearrangement induced by PhI[OC(O)CF3]2 to gi...

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Bibliographic Details
Published in:Journal of peptide science 2005-03, Vol.11 (3), p.175-186
Main Authors: Chulin, A. N., Rodionov, I. L., Baidakova, L. K., Rodionova, L. N., Balashova, T. A., Ivanov, V. T.
Format: Article
Language:English
Subjects:
aminoacyl incorporation reaction
Aminoacylation
Aminobutyrates - chemistry
dilactams
Glutamic Acid - analogs & derivatives
Glutamic Acid - chemical synthesis
Glutamic Acid - chemistry
Hoffman rearrangement
Molecular Structure
Ornithine - chemistry
Oxidation-Reduction
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
PIFA
pyroglutamic acid
Pyrrolidonecarboxylic Acid - chemistry
ring expansion
ruthenium tetroxide
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Summary:A number of protected proline‐containing dipeptides Boc‐Xaa‐Pro‐OBut were converted via epimerization‐free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc‐Xaa‐Glp‐OBut. The latter were subjected to oxidative Hoffman‐type rearrangement induced by PhI[OC(O)CF3]2 to give N‐(aminoacyl)‐pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10‐membered‐ring dilactams derived from 1,4‐diaminobutyric and glutamic acids in practicable yields. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.611