Synthesis of 9-membered dilactams derived from 1,3-diaminopropionic and glutamic acids

:  Previously unknown 9‐membered bridged dipeptides derived from l or d isomers of 1,3‐diaminopropionic acids and l‐glutamic acid were synthesized using aminoacyl incorporation reaction. Key intermediates containing internal pyroglutamyl moiety were prepared via side chain to backbone cyclization of...

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Bibliographic Details
Published in:The journal of peptide research 2004-03, Vol.63 (3), p.235-240
Main Authors: Chulin, A.N., Rodionov, I.L., Ivanov, V.T.
Format: Article
Language:English
Subjects:
aminoacyl incorporation reaction
beta-Alanine - analogs & derivatives
beta-Alanine - chemistry
bridged dipeptides
Combinatorial Chemistry Techniques - methods
Dipeptides - chemical synthesis
Glutamic Acid - chemistry
Hofmann rearrangement
iodobenzene diacetate
Lactams - chemical synthesis
Molecular Structure
ring expansion
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Summary::  Previously unknown 9‐membered bridged dipeptides derived from l or d isomers of 1,3‐diaminopropionic acids and l‐glutamic acid were synthesized using aminoacyl incorporation reaction. Key intermediates containing internal pyroglutamyl moiety were prepared via side chain to backbone cyclization of related protected dipeptide derivatives of glutamic acid.
ISSN:1397-002X
1399-3011
DOI:10.1111/j.1399-3011.2004.00131.x