Abstract
The synthesis of N-aminoimidazolidin-2-one (Aid) peptidomimetics has been achieved by alkylation of the urea nitrogen of a semicarbazone residue using ethylene bromide. The Aid scaffold combines electronic and structural constraints to rigidify the peptide backbone in the equivalent of an aza variant of a Freidinger-Veber lactam. The syntheses and isolation of 25 Aid peptides, including eight GHRP-6 analogues, are reported to demonstrate the utility of this method for controlling conformation.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Amino Acid Sequence
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Aza Compounds / chemical synthesis
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Aza Compounds / chemistry
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Chemistry, Organic / methods
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Lactams / chemical synthesis
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Lactams / chemistry
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Molecular Conformation
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Molecular Structure
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Oligopeptides / chemistry
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Peptides / chemical synthesis*
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Peptides / chemistry*
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Peptidomimetics
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Semicarbazones / chemistry*
Substances
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Aza Compounds
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Lactams
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Oligopeptides
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Peptides
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Peptidomimetics
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Semicarbazones
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growth hormone releasing hexapeptide